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  • Madeira Bay Resort #1602 ~ Gulf View from 6th Floor Balcony ~ Walk to John's Pass
    From $374 per night (USD)

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    Madeira Bay Resort #1602 ~ Gulf View from 6th Floor Balcony ~ Walk to John's Pass

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently clos ...

    From $374 per night (USD)

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    Details
  • Top floor beachfront unit at premier building
    From $462 per night (USD)

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    Top floor beachfront unit at premier building

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    HURRICANE UPDATE: Despite the recent impact of Hurricane Helene & Hurricane Milton, we're pleased to share that cleanup ...

    From $462 per night (USD)

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  • Quaint Madeira Beach Cottage with Heated Pool
    From $169 per night (USD)

    VRBO

    Quaint Madeira Beach Cottage with Heated Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy a Gulf vacation in a private beach cottage located directly across the street from the beach. In less than a one m ...

    From $169 per night (USD)

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  • Madeira Bay Resort I 1505 NEW Complex with a Breathtaking Bayfront View!
    From $266 per night (USD)

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    Madeira Bay Resort I 1505 NEW Complex with a Breathtaking Bayfront View!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Please be aware that our beautiful beach town did experience damage from Hurricanes Helene and Milton. Our community is ...

    From $266 per night (USD)

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    Details
  • Beautiful Madeira Yacht Club Beach Condo-1BR\/ 1.5BA. Sleeps 4 comfortably!
    From $217 per night (USD)

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    Beautiful Madeira Yacht Club Beach Condo-1BR\/ 1.5BA. Sleeps 4 comfortably!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    ACCOMODATIONS: Steps away from the beach and your toes touching the sand! Enjoy leisurely afternoon strolls around the b ...

    From $217 per night (USD)

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  • PRIVACY, RELAX with the DOLPHINS at the SEASIDE,no people. LOUNGERS & UMBRELLA,
    From $264 per night (USD)

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    PRIVACY, RELAX with the DOLPHINS at the SEASIDE,no people. LOUNGERS & UMBRELLA,

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    MADEIRA BEACH. TOTAL PRIVACY at SUNGLOW SEASIDE IS A RARE in TOWN PROPERTY FIND.. SLEEPS 4. THIS GROUND FLOOR END UNIT ...

    From $264 per night (USD)

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  • Luxury Updated Beach Condo - Crimson #104
    From $250 per night (USD)

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    Luxury Updated Beach Condo - Crimson #104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Crimson on the Gulf #104 - You won't need to walk far to the beach from this beautiful condo! Located just steps from th ...

    From $250 per night (USD)

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  • Top Floor Balcony Beach View - Crimson #304
    From $284 per night (USD)

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    Top Floor Balcony Beach View - Crimson #304

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Crimson on the Gulf #304 - This beautiful condo is a popular 2 bedroom, 2 bathroom vacation retreat that is close to eve ...

    From $284 per night (USD)

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  • EXCELLENT Madeira Beach GULF FRONT vacation rental at SEA BREEZE    63202B
    From $352 per night (USD)

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    EXCELLENT Madeira Beach GULF FRONT vacation rental at SEA BREEZE 63202B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Completely updated in fall of 2013- Home away from home- Home Away from Home -Sea Breeze 202 is a GOLD rated corner two- ...

    From $352 per night (USD)

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  • BEST DEALS NOW !AMAZING BEACH, PRIVACY, UNWIND. SLEEP 4, FREE CHAIRS, BBQ, PKG
    From $244 per night (USD)

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    BEST DEALS NOW !AMAZING BEACH, PRIVACY, UNWIND. SLEEP 4, FREE CHAIRS, BBQ, PKG

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    SIMPLY AMAZING MILE OF PRIVATE RESIDENTIAL BEACHFRONT.....SUNGLOW SEASIDE, ST PETERSBURG-MADEIRA BEACH DOWNTOWN CENTRAL ...

    From $244 per night (USD)

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  • **DIRECT BEACH FRONT**GREAT LOCATION** 2 BEDROOM 2 BATH**AWESOME VIEWS**
    From $363 per night (USD)

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    **DIRECT BEACH FRONT**GREAT LOCATION** 2 BEDROOM 2 BATH**AWESOME VIEWS**

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    ***** 8/8/24 - NOTICE: THE ELEVATOR WILL BE REPLACED STARTING ON 9/30/24 AND SHOULD BE COMPLETED BY 11/8/24***** THIS I ...

    From $363 per night (USD)

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  • The New Madeira Bay Resort I 1609 Marina View
    From $271 per night (USD)

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    The New Madeira Bay Resort I 1609 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $271 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1308 Gulf View
    From $341 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1308 Gulf View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $341 per night (USD)

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    Details
  • PENTHOUSE BEACHFRONT, SLEEP 4, <br>  2 MIN to TOWN. FREE LOUNGERS, BBQ, WiFi
    From $261 per night (USD)

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    PENTHOUSE BEACHFRONT, SLEEP 4, <br> 2 MIN to TOWN. FREE LOUNGERS, BBQ, WiFi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    SUNGLOW SEASIDE. A QUAINT PROPERTY, Few PEOPLE, No elevators or congested common areas. COME RELAX by the SEASIDE AT S ...

    From $261 per night (USD)

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  • Surf Song 348 Gulf Front Balcony Across from John's Pass Village
    From $276 per night (USD)

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    Surf Song 348 Gulf Front Balcony Across from John's Pass Village

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This one bedroom, one bathroom condo features a private balcony with a direct Gulf Front view. - Kitchen: Full size app ...

    From $276 per night (USD)

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  • The New Madeira Bay Resort I 1407 Marina View
    From $327 per night (USD)

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    The New Madeira Bay Resort I 1407 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $327 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1701 Marina View
    From $376 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1701 Marina View

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $376 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1301 Marina View
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    The New Madeira Bay Resort I 1301 Marina View

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    The brand new Madeira Bay Resort I #1301 is a three bedroom, two bathroom condo with a private balcony. King size bed in ...

    Click For Pricing

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  • The New Madeira Bay Resort I 1501 Marina View
    From $362 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1501 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $362 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1403 Marina View
    From $314 per night (USD)

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    The New Madeira Bay Resort I 1403 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $314 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1305 Marina View
    From $395 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1305 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $395 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1608 Gulf View
    From $356 per night (USD)

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    The New Madeira Bay Resort I 1608 Gulf View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $356 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1702
    From $305 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1702

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $305 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1601 Marina View
    From $406 per night (USD)

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    The New Madeira Bay Resort I 1601 Marina View

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $406 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1708 Gulf View
    From $341 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1708 Gulf View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $341 per night (USD)

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    Details
  • 2b 2b - Partial Beach View - Sandy Shores #211
    From $442 per night (USD)

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    2b 2b - Partial Beach View - Sandy Shores #211

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sandy Shores #211 - Under new ownership and freshened up with new paint, appliances, kitchen backsplash, bedding, smart ...

    From $442 per night (USD)

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  • The New Madeira Bay Resort I 1401 Marina View
    From $440 per night (USD)

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    The New Madeira Bay Resort I 1401 Marina View

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $440 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1707 Marina View
    From $312 per night (USD)

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    The New Madeira Bay Resort I 1707 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $312 per night (USD)

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    Details
  • Superb Location on the Beaches of Madeira. Great Corner Unit Views. Beachfront Pool on the Sand!
    From $382 per night (USD)

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    Superb Location on the Beaches of Madeira. Great Corner Unit Views. Beachfront Pool on the Sand!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    HURRICANE UPDATE: Despite the recent impact of Hurricane Helene & Hurricane Milton, we're pleased to share that cleanup ...

    From $382 per night (USD)

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    Details
  • Madeira Beach 2 Bedroom, 1 Bath Pool, Hot Tub, Gym
    From $297 per night (USD)

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    Madeira Beach 2 Bedroom, 1 Bath Pool, Hot Tub, Gym

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful 2-bedroom 1 bathroom in the highly sought-after Madeira Beach Yacht Club. A gated, waterfront community is loc ...

    From $297 per night (USD)

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  • The Penthouse at Madeira Beach 5 bedroom (sleeps 14) gorgeous Gulf views
    From $1000 per night (USD)

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    The Penthouse at Madeira Beach 5 bedroom (sleeps 14) gorgeous Gulf views

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    ****THIS CONDO WAS NOT DAMAGED IN THE RECENT HURRICANE. THE STREET SIDE ELEVATOR IS WORKING, HOWEVER, THE POOL IS IS NOT ...

    From $1000 per night (USD)

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  • ☀️Happy Home-Across Street from Beach-3BR-Madeira Beach-Great Location☀️
    From $394 per night (USD)

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    ☀️Happy Home-Across Street from Beach-3BR-Madeira Beach-Great Location☀️

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Please be aware that our beautiful beach town did experience damage from Hurricanes Helene and Milton. Our community is ...

    From $394 per night (USD)

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  • Sand Beach lifestyle and boardwalk vacation house
    From $892 per night (USD)

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    Sand Beach lifestyle and boardwalk vacation house

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome "Madeira Beach Area" - just steps from the beautiful white-sanded Beach and famous John's Pass Boardwalk! Great ...

    From $892 per night (USD)

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  • Ocean Sands 1107: Amazing Gulf Front Retreat in
    From $287 per night (USD)

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    Ocean Sands 1107: Amazing Gulf Front Retreat in

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amazing 11th floor 2 bedroom 2 bath Gulf Front condo with upgrades galore and panoramic views from every window! There's ...

    From $287 per night (USD)

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  • Stunning Top Floor Views and an Interior to Match. On the Beach. Close to Johns Pass Village.
    From $274 per night (USD)

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    Stunning Top Floor Views and an Interior to Match. On the Beach. Close to Johns Pass Village.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    HURRICANE UPDATE: Despite the recent impact of Hurricane Helene & Hurricane Milton, we're pleased to share that cleanup ...

    From $274 per night (USD)

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    Details
  • Top Floor Overlooking the Marina. Close to Johns Pass. Spacious with Two Private Balconies!
    From $389 per night (USD)

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    Top Floor Overlooking the Marina. Close to Johns Pass. Spacious with Two Private Balconies!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    HURRICANE UPDATE: Despite the recent impact of Hurricane Helene & Hurricane Milton, we're pleased to share that cleanup ...

    From $389 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1405 Marina View
    From $313 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1405 Marina View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool is currently not ...

    From $313 per night (USD)

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    Details
  • Villas at John's Pass 01 just 1 Block to the Village and the Beach
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    Villas at John's Pass 01 just 1 Block to the Village and the Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    The" Villas at John's Pass" is a small property of just 4 units, located on the North end of the historic boardwalk and ...

    Click For Pricing

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  • Villas at John's Pass 04 just 1 Block to the Village and the Beach
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    Villas at John's Pass 04 just 1 Block to the Village and the Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    The" Villas at John's Pass" is a small property of just 4 units, located on the North end of the historic boardwalk and ...

    Click For Pricing

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    Details
  • Madeira Bay Resort 209  Marina View w\/Beach Access
    From $268 per night (USD)

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    Madeira Bay Resort 209 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Madeira Bay Resort #209 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $268 per night (USD)

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  • Villas at John's Pass 02 just 1 Block to the Village and the Beach
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    Villas at John's Pass 02 just 1 Block to the Village and the Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    The" Villas at John's Pass" is a small property of just 4 units, located on the North end of the historic boardwalk and ...

    Click For Pricing

    VRBO

    Details
  • Villas at John's Pass 03 just 1 Block to the Village and the Beach
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    Villas at John's Pass 03 just 1 Block to the Village and the Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    The" Villas at John's Pass" is a small property of just 4 units, located on the North end of the historic boardwalk and ...

    Click For Pricing

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    Details
  • Madeira Bay Resort 316 Beach Access
    From $253 per night (USD)

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    Madeira Bay Resort 316 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #316 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a queen size ...

    From $253 per night (USD)

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  • Stunning 3 bed\/2 bath beachfront condo in Madeira Beach, FL
    From $476 per night (USD)

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    Stunning 3 bed\/2 bath beachfront condo in Madeira Beach, FL

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The beachfront condo directly overlooks the glistening Gulf of Mexico and sparkling white, sandy beach of Madeira Beach, ...

    From $476 per night (USD)

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  • Sea Breeze 707 Gulf Front Balcony with Heated Pool
    From $408 per night (USD)

    VRBO

    Sea Breeze 707 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #707 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $408 per night (USD)

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    Details
  • Las Brisas 407 3BR 2BA Gulf Front
    From $459 per night (USD)

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    Las Brisas 407 3BR 2BA Gulf Front

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Las Brisas #407 is a spacious 3 bedroom, 2 bathroom condo with a balcony. Stunning direct gulf front view. The master be ...

    From $459 per night (USD)

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  • Madeira Bay Resort 414 Beach Access
    From $251 per night (USD)

    VRBO

    Madeira Bay Resort 414 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #414 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $251 per night (USD)

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    Details
  • Sea Breeze 505 Gulf Front Balcony with Heated Pool
    From $426 per night (USD)

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    Sea Breeze 505 Gulf Front Balcony with Heated Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Sea Breeze #505 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious 710 sq. ft. fl ...

    From $426 per night (USD)

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    Details
  • Madeira Bay Resort 313 Marina View w\/Beach Access
    From $306 per night (USD)

    VRBO

    Madeira Bay Resort 313 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #313 is a two bedroom, two bathroom condo with a private balcony. View of marina, sunrises, waterway ...

    From $306 per night (USD)

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    Details
  • Villa Madeira 601 Gulf Front Corner Unit Large Balcony
    From $423 per night (USD)

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    Villa Madeira 601 Gulf Front Corner Unit Large Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Villa Madeira is a Gulf Front property with large screened balconies. Expansive view of the Gulf of Mexico. So close to ...

    From $423 per night (USD)

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    Details
  • Madeira Bay Resort 506 Gulf View w\/Beach Access
    From $294 per night (USD)

    VRBO

    Madeira Bay Resort 506 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #506 is a two bedroom, two bathroom condo with two private balconies. The master bedroom has a king s ...

    From $294 per night (USD)

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    Details
  • Villa Madeira 610 Gulf Front Large Balcony
    From $448 per night (USD)

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    Villa Madeira 610 Gulf Front Large Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Villa Madeira is a Gulf Front property with large screened balconies. Expansive view of the Gulf of Mexico. So close to ...

    From $448 per night (USD)

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    Details
  • Madeira Bay Resort 307 Marina View w\/Beach Access
    From $266 per night (USD)

    VRBO

    Madeira Bay Resort 307 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #307 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $266 per night (USD)

    VRBO

    Details
  • Gulf Lane 2BR Beach House w\/Private Path to Beach
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    Gulf Lane 2BR Beach House w\/Private Path to Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    This two bedroom, one bathroom beach house is Gulf Front and offers a large deck overlooking the beach! Lots of natural ...

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  • Madeira Bay Resort 416 Beach Access
    From $229 per night (USD)

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    Madeira Bay Resort 416 Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #416 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $229 per night (USD)

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    Details
  • Madeira Bay Resort 410
    From $297 per night (USD)

    Expedia

    Madeira Bay Resort 410

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #410 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $297 per night (USD)

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    Details
  • Sea Breeze 508 Gulf Front Balcony with Heated Pool
    From $315 per night (USD)

    VRBO

    Sea Breeze 508 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #508 is a direct Gulf Front condo with a large private balcony overlooking the beach. This corner unit also h ...

    From $315 per night (USD)

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  • Sea Breeze 301 Gulf Front Balcony with Heated Pool
    From $371 per night (USD)

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    Sea Breeze 301 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #301 is a direct Gulf Front condo with a large private balcony overlooking the beach. This corner unit also h ...

    From $371 per night (USD)

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    Details
  • Madeira Bay Resort 205 Beach Access
    From $249 per night (USD)

    VRBO

    Madeira Bay Resort 205 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #205 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a queen size ...

    From $249 per night (USD)

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    Details
  • Madeira Bay Resort 413 Marina View w\/Beach Access
    From $238 per night (USD)

    Expedia

    Madeira Bay Resort 413 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Madeira Bay Resort #413 is a two bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wate ...

    From $238 per night (USD)

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    Details
  • Sea Breeze 703 Gulf Front Balcony with Heated Pool
    From $407 per night (USD)

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    Sea Breeze 703 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #703 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $407 per night (USD)

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    Details
  • Madeira Bay Resort 301 Marina View w\/Beach Access
    From $243 per night (USD)

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    Madeira Bay Resort 301 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #301 is a one bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $243 per night (USD)

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    Details
  • Madeira Bay Resort 207 Marina View w\/Beach Access
    From $268 per night (USD)

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    Madeira Bay Resort 207 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Madeira Bay Resort #207 is a two bedroom, one bathroom condo with a private balcony. View of marina, sunrises, waterway ...

    From $268 per night (USD)

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    Details
  • Madeira Bay Resort 610 Gulf View w\/Beach Access
    From $332 per night (USD)

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    Madeira Bay Resort 610 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #610 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $332 per night (USD)

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    Details
  • Sea Breeze 402 Gulf Front Balcony with Heated Pool
    From $362 per night (USD)

    VRBO

    Sea Breeze 402 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sea Breeze #402 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $362 per night (USD)

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    Details
  • Sea Breeze 406 Gulf Front Balcony with Heated Pool
    From $427 per night (USD)

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    Sea Breeze 406 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sea Breeze #406 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $427 per night (USD)

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    Details
  • Las Brisas 207 Gulf Front Large Balcony Sleeps 9
    From $436 per night (USD)

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    Las Brisas 207 Gulf Front Large Balcony Sleeps 9

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Las Brisas #207 is a beautiful Gulf front corner unit condo with large balcony. With 3 bedrooms and 2 bathroom, this is ...

    From $436 per night (USD)

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    Details
  • Sea Breeze 203 Gulf Front Balcony with Heated Pool
    From $358 per night (USD)

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    Sea Breeze 203 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #203 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $358 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 510 Gulf View w\/Beach Access
    From $292 per night (USD)

    VRBO

    Madeira Bay Resort 510 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #510 is a two bedroom, two bathroom condo with a private balcony. The master and second bedroom both ...

    From $292 per night (USD)

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    Details
  • Madeira Bay Resort 206 Marina View w\/Beach Access
    From $336 per night (USD)

    Expedia

    Madeira Bay Resort 206 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #206 is a two bedroom, one bathroom condo with private balcony. The master bedroom has a king size be ...

    From $336 per night (USD)

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    Details
  • Villa Madeira 606 Gulf Front Large Balcony
    From $363 per night (USD)

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    Villa Madeira 606 Gulf Front Large Balcony

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    Villa Madeira is a Gulf Front property with large screened balconies. Expansive view of the Gulf of Mexico. So close to ...

    From $363 per night (USD)

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    Details
  • Madeira Bay Resort 611 ~ TOP FLOOR GREAT VIEWS OF THE BEACH AND CITY, CORNER UNIT FOR GREAT PRIVACY
    From $283 per night (USD)

    Expedia

    Madeira Bay Resort 611 ~ TOP FLOOR GREAT VIEWS OF THE BEACH AND CITY, CORNER UNIT FOR GREAT PRIVACY

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #611 is a TOP FLOOR CORNER UNIT, offering stunning views of both the beach and city. Its corner locat ...

    From $283 per night (USD)

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    Details
  • Madeira Bay Resort 210 Marina View w\/Beach Access
    From $290 per night (USD)

    VRBO

    Madeira Bay Resort 210 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #210 is a two bedroom, two bathroom condo with a private balcony. Corner balcony with access from liv ...

    From $290 per night (USD)

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    Details
  • Madeira Bay Resort 602 Gulf View w\/Beach Access
    From $284 per night (USD)

    Expedia

    Madeira Bay Resort 602 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #602 is a two bedroom, two bathroom condo with two private balconies. The master bedroom has a king s ...

    From $284 per night (USD)

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    Details
  • Madeira Bay Resort 402 Beach Access
    From $265 per night (USD)

    VRBO

    Madeira Bay Resort 402 Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #402 is a one bedroom, one bathroom condo with a private balcony. This spacious floorplan is handicap ...

    From $265 per night (USD)

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    Details
  • Madeira Bay Resort 412 Marina View w\/Beach Access
    From $221 per night (USD)

    Expedia

    Madeira Bay Resort 412 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #412 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $221 per night (USD)

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    Details
  • Madeira Bay Resort 208 Beach Access
    From $219 per night (USD)

    VRBO

    Madeira Bay Resort 208 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #208 is a two bedroom, two bathroom condo and private balcony. The master bedroom has a queen size be ...

    From $219 per night (USD)

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    Details
  • Sea Breeze 305 Gulf Front Balcony with Heated Pool
    From $336 per night (USD)

    Expedia

    Sea Breeze 305 Gulf Front Balcony with Heated Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Sea Breeze #305 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious 710 sq. ft. fl ...

    From $336 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 504 Marina View w\/Beach Access
    From $280 per night (USD)

    VRBO

    Madeira Bay Resort 504 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #504 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $280 per night (USD)

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    Details
  • Madeira Bay Resort 404 Beach Access
    From $270 per night (USD)

    Expedia

    Madeira Bay Resort 404 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Enjoy our updated Madeira Beach condo with a great location to beach and John's Pass! Madeira Bay Resort #404 is a two b ...

    From $270 per night (USD)

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    Details
  • Madeira Bay Resort 608 Marina View w\/Beach Access
    From $310 per night (USD)

    VRBO

    Madeira Bay Resort 608 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #608 is a two bedroom, two bathroom condo with two private balconies. Spacious corner unit with views ...

    From $310 per night (USD)

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  • Gulf Lane 1BR Beach House w\/Private Path to Beach
    Click For Pricing

    Expedia

    Gulf Lane 1BR Beach House w\/Private Path to Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This one bedroom, one bathroom beach house is Gulf Front and offers a large deck overlooking the beach! Lots of natural ...

    Click For Pricing

    Expedia

    Details
  • Villa Madeira 304 Gulf Front Large Balcony Sleeps 8
    From $507 per night (USD)

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    Villa Madeira 304 Gulf Front Large Balcony Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Villa Madeira is a Gulf Front property with large screened balconies. Expansive view of the Gulf of Mexico. So close to ...

    From $507 per night (USD)

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    Details
  • Chambre #301 Beach Front Balcony and Pool
    From $322 per night (USD)

    Expedia

    Chambre #301 Beach Front Balcony and Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Spend your days relaxing by the heated pool or in the sparkling waters of the Gulf and be sure to get the white sugar sa ...

    From $322 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 408 Marina View w\/Beach Access
    From $247 per night (USD)

    VRBO

    Madeira Bay Resort 408 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #408 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $247 per night (USD)

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    Details
  • Madeira Bay Resort 314 Beach Access
    From $295 per night (USD)

    Expedia

    Madeira Bay Resort 314 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Hurricane Update: This condo was not damaged in the hurricanes! We'd love to accommodate you. The pool and elevator are ...

    From $295 per night (USD)

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    Details
  • Madeira Bay Resort 415 Beach Access
    From $338 per night (USD)

    VRBO

    Madeira Bay Resort 415 Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #415 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $338 per night (USD)

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    Details
  • Madeira Bay Resort 501 Gulf View w\/Beach Access
    From $249 per night (USD)

    Expedia

    Madeira Bay Resort 501 Gulf View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #501 is a one bedroom, one bathroom condo with a private balcony. This spacious floorplan is handicap ...

    From $249 per night (USD)

    Expedia

    Details
  • Sea Breeze 403 Gulf Front Balcony with Heated Pool
    From $301 per night (USD)

    VRBO

    Sea Breeze 403 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #403 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $301 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 505 Marina View w\/Beach Access
    From $406 per night (USD)

    Expedia

    Madeira Bay Resort 505 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Madeira Bay Resort #505 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $406 per night (USD)

    Expedia

    Details
  • Sea Breeze 206 Gulf Front Balcony with Heated Pool
    From $424 per night (USD)

    VRBO

    Sea Breeze 206 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sea Breeze #206 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $424 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 502 Marina View w\/Beach Access
    From $292 per night (USD)

    Expedia

    Madeira Bay Resort 502 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #502 is a two bedroom, two bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $292 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 604 Marina View w\/Beach Access
    From $384 per night (USD)

    VRBO

    Madeira Bay Resort 604 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Madeira Bay Resort #604 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $384 per night (USD)

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    Details
  • Madeira Bay Resort 507 Marina View w\/Beach Access
    From $361 per night (USD)

    Expedia

    Madeira Bay Resort 507 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Madeira Bay Resort #507 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $361 per night (USD)

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    Details
  • Large Family Condo with Outstanding View of the Beach
    From $541 per night (USD)

    VRBO

    Large Family Condo with Outstanding View of the Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Las Brisas 201 is a recently renovated 1440 square foot condo with 3 bedrooms and 2 bathrooms. You can take pleasure in ...

    From $541 per night (USD)

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    Details
  • Luxury Beachfront Corner Condo 3 BR 2 BA with a Pool - It’s 5 o’clock somewhere!
    From $368 per night (USD)

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    Luxury Beachfront Corner Condo 3 BR 2 BA with a Pool - It’s 5 o’clock somewhere!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    This newly remodeled Villa Madeira condo is a large north corner unit that has a screened in balcony facing the white sa ...

    From $368 per night (USD)

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    Details
  • Surf Song 223 Escape to Island Life
    Click For Pricing

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    Surf Song 223 Escape to Island Life

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song Resort #223 Escape to island life in this 2 bedroom, 2 bath poolside condo on the second floor with a view of ...

    Click For Pricing

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  • Surf Song 119 Coastal Retreat on Madeira Beach
    Click For Pricing

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    Surf Song 119 Coastal Retreat on Madeira Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Surf Song Resort #119 You will feel like you're on vacation the moment you step into this 2 bedroom, 2 bath poolside co ...

    Click For Pricing

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    Details
  • Surf Song 236 Beach Vibes
    From $190 per night (USD)

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    Surf Song 236 Beach Vibes

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This one bedroom, one bathroom condo offers all the convenience of being beach side and even has a partial view of the G ...

    From $190 per night (USD)

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    Details
  • Surf Song 237 Florida Charm on Madeira Beach
    From $232 per night (USD)

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    Surf Song 237 Florida Charm on Madeira Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song Resort #237 12960 Gulf Blvd, Madeira Beach, FL 33708 TRS office located just a block away: 13030 Gulf Blvd, Ma ...

    From $232 per night (USD)

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