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Results: 913 Rentals

  • Sea Grape Inn #7 - Beachfront Property
    From $591 per night (USD)

    VRBO

    Sea Grape Inn #7 - Beachfront Property

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 1-Queen, 1-Sofa Sleeper ** Ne ...

    From $591 per night (USD)

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    Details
  • Sea Grape Inn #5- Beachfront Property
    From $580 per night (USD)

    Expedia

    Sea Grape Inn #5- Beachfront Property

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. ...

    From $580 per night (USD)

    Expedia

    Details
  • Sea Grape Inn #4- Beachfront Property
    From $591 per night (USD)

    VRBO

    Sea Grape Inn #4- Beachfront Property

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen. ** Need to stay less ...

    From $591 per night (USD)

    VRBO

    Details
  • On the beach, Sunset view, Monthly rental 2B\/B2 Pool&Tennis
    From $343 per night (USD)

    Expedia

    On the beach, Sunset view, Monthly rental 2B\/B2 Pool&Tennis

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The view is amazing! The condo overlooks the pristine white sand beach and has a beautiful Gulf view. This second floor ...

    From $343 per night (USD)

    Expedia

    Details
  • Luxurious Beachfront Villa with Private Pool
    From $236 per night (USD)

    VRBO

    Luxurious Beachfront Villa with Private Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This three-bedroom, three-bathroom unit is 2,200 square feet and steps from the Gulf of Mexico. Guests will enjoy a secl ...

    From $236 per night (USD)

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    Details
  • Beachcomber unit 401
    From $338 per night (USD)

    Expedia

    Beachcomber unit 401

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...

    From $338 per night (USD)

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    Details
  • Gulf Getaway with Porch + Direct Beach Access!
    From $302 per night (USD)

    VRBO

    Gulf Getaway with Porch + Direct Beach Access!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Pack your sunscreen when you embrace a coastal retreat at this 1-bedroom, 1-bathroom vacation rental condo located in th ...

    From $302 per night (USD)

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    Details
  • 2 Bedroom Beachfront Condo by FVC
    From $608 per night (USD)

    Expedia

    2 Bedroom Beachfront Condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Offered by FL Vacation Connection, this perfect island getaway is located on the southern tip of Longboat Key with a bea ...

    From $608 per night (USD)

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    Details
  • Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
    From $404 per night (USD)

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    Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Your Coastal Oasis at Cabana Beach Club Unit 8! NO MAJOR HURRICANE DAMAGE!!! Just a two-minute stroll from pr ...

    From $404 per night (USD)

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    Details
  • GULF FRONT CONDO \/ PRIVATE PATIO \/ STEPS TO THE BEACH
    From $609 per night (USD)

    Expedia

    GULF FRONT CONDO \/ PRIVATE PATIO \/ STEPS TO THE BEACH

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our Ground floor BEACHFRONT condo unit #119 at the beautiful Sand Cay Beach Resort on Longboat Key! Magnific ...

    From $609 per night (USD)

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    Details
  • Whitney Beach #336 Condo by RVA
    From $224 per night (USD)

    VRBO

    Whitney Beach #336 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on a superb pristine beach with ne ...

    From $224 per night (USD)

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  • This AMAZING 2\/2 has stunning views of the bay!
    From $352 per night (USD)

    Expedia

    This AMAZING 2\/2 has stunning views of the bay!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Due to Hurricane Helene, our properties are still recovering and updating until further notice. Harbor Villa Club is no ...

    From $352 per night (USD)

    Expedia

    Details
  • Love the beach? Tennis? Swimming? This great family friendly retreat has it all!
    From $353 per night (USD)

    VRBO

    Love the beach? Tennis? Swimming? This great family friendly retreat has it all!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Spacious 2400 square foot elevated home (there are 16 steps to enter and exit) featuring wide open floor plan with vault ...

    From $353 per night (USD)

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    Details
  • Luxury Beach Front Condo on the most private and select beach in Longboat Key!
    From $249 per night (USD)

    VRBO

    Luxury Beach Front Condo on the most private and select beach in Longboat Key!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Are you looking for a quiet and select, non-touristy location right on what happens to be one of the most spectacular an ...

    From $249 per night (USD)

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  • Newly Remodeled!  Directly Across from Beach ~ Condo
    From $132 per night (USD)

    VRBO

    Newly Remodeled! Directly Across from Beach ~ Condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The location of the condo is fantastic as you will have access to the luxurious Longboat Key Beach nearly to yourself. T ...

    From $132 per night (USD)

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    Details
  • Cedars East #519 Townhome by RVA
    From $354 per night (USD)

    Expedia

    Cedars East #519 Townhome by RVA

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...

    From $354 per night (USD)

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  • Unit #212 Sand Cay Beach Resort Pool and Garden View
    From $442 per night (USD)

    VRBO

    Unit #212 Sand Cay Beach Resort Pool and Garden View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Tastefully renovated, non-smoking, second floor unit. New updates every year. Light and bright with all the comforts of ...

    From $442 per night (USD)

    VRBO

    Details
  • Inn on the Beach 3007 by FVC
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    Inn on the Beach 3007 by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Offered by FL Vacation Connection, this island getaway is located on the southern tip of Longboat Key with beautiful bea ...

    Click For Pricing

    Expedia

    Details
  • Luxury 2 bedroom Beachfront Condo by FVC
    From $1234 per night (USD)

    VRBO

    Luxury 2 bedroom Beachfront Condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FL Vacation Connection offers this 2brm luxury condo. 3rd floor. 1700 sq ft. 52' beachfront balcony. Large Living, dini ...

    From $1234 per night (USD)

    VRBO

    Details
  • FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3\/29 - 4\/5  2025
    From $814 per night (USD)

    Expedia

    FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3\/29 - 4\/5 2025

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    WE ARE RENTING A FANTASTIC KEY WEST STYLE COTTAGE ON THE BEACH OF LONGBOAT KEY FLORIDA. JUST STEPS TO THE LOVELY BEACH ...

    From $814 per night (USD)

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  • Unit #207 Sand Cay Beach Resort Pool and Garden View
    From $477 per night (USD)

    VRBO

    Unit #207 Sand Cay Beach Resort Pool and Garden View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Second floor,.. It's very cozy with all the comforts of home. This renovated unit has an updated kitchen and baths wit ...

    From $477 per night (USD)

    VRBO

    Details
  • Sea Grape Inn #1- Beachfront Property
    From $806 per night (USD)

    Expedia

    Sea Grape Inn #1- Beachfront Property

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    BEACH FRONT Condo- 1st Floor of Beach Front Property, 2 BDRM/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. ...

    From $806 per night (USD)

    Expedia

    Details
  • Beachcomber unit 205
    From $353 per night (USD)

    VRBO

    Beachcomber unit 205

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Our building is located on the beach, this unit has an ISLAND view. Beautifully renovated 1 bedroom, 1 bath ...

    From $353 per night (USD)

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    Details
  • Tropical Paradise - boutique house and cottage with outdoor entertainment deck
    From $589 per night (USD)

    Expedia

    Tropical Paradise - boutique house and cottage with outdoor entertainment deck

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This house, located in a prime location next door to the best restaurant on the Island, is a tropical paradise that you ...

    From $589 per night (USD)

    Expedia

    Details
  • Penthouse timeshare
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    VRBO

    Penthouse timeshare

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    A rare opportunity to escape to your four bedroom penthouse on the beach in Longboat Key or for a week in February (2/5/ ...

    Click For Pricing

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    Details
  • Veranda Beach Club, beachfront Longboat Key, Florida
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    Veranda Beach Club, beachfront Longboat Key, Florida

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit #309, a beach front condo, is available Weeks #51 & #52 2019, and Week #1 2020. Unit #306, with a partial ocean vi ...

    Click For Pricing

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  • Amazing 2\/2 Condo LBK w\/ Spectacular Bay Views!
    From $621 per night (USD)

    VRBO

    Amazing 2\/2 Condo LBK w\/ Spectacular Bay Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Longboat Key is perfect for a dream vacation on an island! This condo offers a stunning 180-degree view of Sarasota Bay. ...

    From $621 per night (USD)

    VRBO

    Details
  • Private Island Retreat with Private Beach,  Dock, Palm Trees & Glorious Sunsets
    From $1638 per night (USD)

    Expedia

    Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Set on 2 acres of land on a 38 acre private island, this award winning home will provide an island vacation experience f ...

    From $1638 per night (USD)

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    Details
  • Renovated Beach Paradise. Ground Floor unit 64
    From $294 per night (USD)

    VRBO

    Renovated Beach Paradise. Ground Floor unit 64

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Completely renovated. Everything is new. Amazing location. Condo management will help you with your accommodation. The u ...

    From $294 per night (USD)

    VRBO

    Details
  • Longboat Village Getaway: House on Longboat Key by RVA
    From $463 per night (USD)

    Expedia

    Longboat Village Getaway: House on Longboat Key by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Step into tranquility with Longboat Village Getaway, a charming two-bedroom, two-bathroom stilted home nestled on the pe ...

    From $463 per night (USD)

    Expedia

    Details
  • 2 BR Beach front villa with enclosed lanai overlooking the pool
    From $463 per night (USD)

    VRBO

    2 BR Beach front villa with enclosed lanai overlooking the pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This 2 bedroom home with a split floor plan works beautifully to accommodate your family's vacation. You walk into a wel ...

    From $463 per night (USD)

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    Details
  • Retreat Between the Beach & Bay
    From $284 per night (USD)

    Expedia

    Retreat Between the Beach & Bay

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    The quaintness of our condo and its location are unmatched. This 2B/2B unit is steps away from the bay, and merely acros ...

    From $284 per night (USD)

    Expedia

    Details
  • Veranda Beach Club, ( Week 2 )  Jan. 11 to 18, 2020
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    Veranda Beach Club, ( Week 2 ) Jan. 11 to 18, 2020

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautifully furnished beach front property, Second floor corner garden unit with two balconies. Private beach with umbr ...

    Click For Pricing

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  • This beautiful unit has front row seats to the sunrise! Direct bayfront! Call today for your holiday stay!
    From $321 per night (USD)

    Expedia

    This beautiful unit has front row seats to the sunrise! Direct bayfront! Call today for your holiday stay!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Due to Hurricane Helene, our properties are still recovering and updating until further notice. Harbor Villa Club is no ...

    From $321 per night (USD)

    Expedia

    Details
  • Longboat Key with Gulf to Bay access. Beautiful view of Bishop's Bayou.
    From $230 per night (USD)

    VRBO

    Longboat Key with Gulf to Bay access. Beautiful view of Bishop's Bayou.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Outdoor living at its best in this updated WATERFRONT first floor condo in Whitney Beach Bay Side. Mesmerizing views of ...

    From $230 per night (USD)

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    Details
  • Breathtaking Beach Front Property Ground Floor Condo
    From $363 per night (USD)

    Expedia

    Breathtaking Beach Front Property Ground Floor Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Granite and stainless steel appliances in the kitchen. The living room’s sliding patio door provides first floor access ...

    From $363 per night (USD)

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  • Spectacular Sarasota Bay Views from all rooms
    From $289 per night (USD)

    VRBO

    Spectacular Sarasota Bay Views from all rooms

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Seasonal Rental. Spectacular views of Sarasota Bay and the Gulf of Mexico from this island penthouse condo. Enjoy the ma ...

    From $289 per night (USD)

    VRBO

    Details
  • Sea Grape Inn #6- Beachfront Property
    From $553 per night (USD)

    Expedia

    Sea Grape Inn #6- Beachfront Property

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. ...

    From $553 per night (USD)

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  • Sea Grape Inn #2- Beachfront Property
    From $584 per night (USD)

    VRBO

    Sea Grape Inn #2- Beachfront Property

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper, ...

    From $584 per night (USD)

    VRBO

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  • Beautiful beachfront condo on Longboat Key, FL!!!
    From $455 per night (USD)

    VRBO

    Beautiful beachfront condo on Longboat Key, FL!!!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Direct Beachfront, Longboat Key remodeled 2/2 Condo in Beachplace. Beautiful Beachplace is a gated community located on ...

    From $455 per night (USD)

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    Details
  • 637 Norton - Longboat Key - Private canal home 4 Bedroom\/ 3.5 Bath with...
    From $800 per night (USD)

    VRBO

    637 Norton - Longboat Key - Private canal home 4 Bedroom\/ 3.5 Bath with...

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    637 Norton - Longboat Key - 4 Bedroom/ 3.5 Bath, maximum occupancy of 8 people. Canal Home - Private Pool - Boat D ...

    From $800 per night (USD)

    VRBO

    Details
  • The Beach on Longboat Key #221 Resort by RVA
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    The Beach on Longboat Key #221 Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium co ...

    Click For Pricing

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  • Longboat Key Resort Escape - Walk to the Beach!
    From $277 per night (USD)

    VRBO

    Longboat Key Resort Escape - Walk to the Beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Prepare yourself for a Gulf Coast getaway at this welcoming 1-bed, 1-bath vacation rental nestled in the tropical Beach ...

    From $277 per night (USD)

    VRBO

    Details
  • Blue Heron House on Longboat Key by RVA
    From $247 per night (USD)

    Expedia

    Blue Heron House on Longboat Key by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Blue Heron House by RVA. This three-bedroom plus office, two-bathroom house is located on the Northern end of ...

    From $247 per night (USD)

    Expedia

    Details
  • Ocean view Longboat Key condo
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    Ocean view Longboat Key condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 BR/2 BA spacious condo timeshare at the Veranda Beach Club in Longboat Key with Gulf of Mexico views from the balcony. ...

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  • DIRECT BAYFRONT VIEWS ON LONGBOAT KEY! Fall dates available
    From $307 per night (USD)

    Expedia

    DIRECT BAYFRONT VIEWS ON LONGBOAT KEY! Fall dates available

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Due to Hurricane Helene, our properties are still recovering and updating until further notice. Harbor Villa Club is no ...

    From $307 per night (USD)

    Expedia

    Details
  • LONGBOAT KEY BEAUTY! This 2\/2 unit offers stunning views of the bay! Call today to book your fall vacation!
    From $300 per night (USD)

    VRBO

    LONGBOAT KEY BEAUTY! This 2\/2 unit offers stunning views of the bay! Call today to book your fall vacation!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Due to Hurricane Helene, our properties are still recovering and updating until further notice. Harbor Villa Club is no ...

    From $300 per night (USD)

    VRBO

    Details
  • The Beach on Longboat Key #221S Resort by RVA
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    Expedia

    The Beach on Longboat Key #221S Resort by RVA

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium co ...

    Click For Pricing

    Expedia

    Details
  • Little Gull Resort - Longboat Key, Florida
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    Little Gull Resort - Longboat Key, Florida

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Large 4 bedroom Suite on beautiful Sarasota Bay. 2 bathroom Pull-out sofa bed sleeps 2. Large verandah with a great vie ...

    Click For Pricing

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  • Right on the beach.Renovated ground Floor unit 63.
    From $295 per night (USD)

    Expedia

    Right on the beach.Renovated ground Floor unit 63.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Completely renovated. Everything is new. Amazing location. Charming studio right on the beach. Condo management will he ...

    From $295 per night (USD)

    Expedia

    Details
  • Beach Front. No Street Crossing. Two Bedroom. 2 Full kitchens. 2 Full bathrooms.
    From $714 per night (USD)

    VRBO

    Beach Front. No Street Crossing. Two Bedroom. 2 Full kitchens. 2 Full bathrooms.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    NO HURRICANE HELENE AND MILTON DAMAGES! BEACH IS OPEN. POOL IS CLEANED, UP AND RUNNING. GROUND AREA IS CLEANED! WE ARE ...

    From $714 per night (USD)

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    Details
  • beachfront condo on 6th floor of the   longboat key club resort !
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    beachfront condo on 6th floor of the longboat key club resort !

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    6th floor bedroom king suite with 1 bathroom living room area with pull out queen bed and kitchen with washer dryer con ...

    Click For Pricing

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  • Longboat Key Cottage: Extended Stays Welcome!
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    Longboat Key Cottage: Extended Stays Welcome!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Head to Florida for a much-needed, month-long getaway when you book and stay at this amenity-packed 2-bedroom, 2-bathroo ...

    Click For Pricing

    VRBO

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  • 2 Bd\/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico 3-6 month rental
    From $169 per night (USD)

    Expedia

    2 Bd\/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico 3-6 month rental

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Available from June 1st - December 15, 2023. Long-term renter desired. Beautiful corner unit condo with an abundance of ...

    From $169 per night (USD)

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  • Beautiful Longboat Key, Florida - Little Gull Resort
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    Beautiful Longboat Key, Florida - Little Gull Resort

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Large 2 bedroom, 2 bathroom suite (plus pull-out sofa bed) Fully equipped kitchen with dishwasher 3 TVs and WIFI Firepla ...

    Click For Pricing

    VRBO

    Details
  • Sea Grape Inn#8- Beach Front Condo
    From $1000 per night (USD)

    Expedia

    Sea Grape Inn#8- Beach Front Condo

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    BEACH FRONT Condo- 2nd Floor of Beach Front Property, 3 Bdrms/2.5 Baths or UPGRADE to 4 Bdrms/ 3.5 Baths Condo! 3 BDRMS ...

    From $1000 per night (USD)

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  • Longbeach Lucky #13 Condo by RVA
    From $219 per night (USD)

    VRBO

    Longbeach Lucky #13 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    No luck needed here to know you've stumbled upon one of the best spots Longboat Key has to offer. Longbeach Lucky 13 by ...

    From $219 per night (USD)

    VRBO

    Details
  • Exquisite Beachfront Condo with both Sunrise & Sunset Views
    From $302 per night (USD)

    Expedia

    Exquisite Beachfront Condo with both Sunrise & Sunset Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A tropical treasure is waiting for you. Newly renovated beachfront beauty with Tommy Bahama inspired furnishings through ...

    From $302 per night (USD)

    Expedia

    Details
  • SPECTACULAR GULF OF MEXICO VIEWS ON LONGBOAT KEY!!
    From $306 per night (USD)

    VRBO

    SPECTACULAR GULF OF MEXICO VIEWS ON LONGBOAT KEY!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    3 bedroom, 2 full bath 3rd Floor (Top Floor)-Southwest Corner 1500+ sq./ft. of living space Bedrooms (Sleeps 6): Bedroo ...

    From $306 per night (USD)

    VRBO

    Details
  • Sunlit Longboat Key Escape w\/ Private Resort Beach
    From $304 per night (USD)

    Expedia

    Sunlit Longboat Key Escape w\/ Private Resort Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Whether you're looking to escape the mid-winter blues or satisfy your saltwater craving, this bright and airy 1-bedroom, ...

    From $304 per night (USD)

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    Details
  • Silver Sands on the Sea!
    From $441 per night (USD)

    VRBO

    Silver Sands on the Sea!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in excl ...

    From $441 per night (USD)

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    Details
  • Paradise!  Gulf beach, On bay, bike, fish, kayak, relax, shop, swim, tennis.....
    From $142 per night (USD)

    Expedia

    Paradise! Gulf beach, On bay, bike, fish, kayak, relax, shop, swim, tennis.....

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful condo located on 2nd floor. End unit overlooking beautiful tropical plants and offering natural light ! Turn ...

    From $142 per night (USD)

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    Details
  • Beachplace 11-303 Condo by RVA
    From $199 per night (USD)

    VRBO

    Beachplace 11-303 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RVA offers this comfortably appointed two-bedroom, two-bathroom condominium in the desirable gated community of Beachpla ...

    From $199 per night (USD)

    VRBO

    Details
  • Private home, North End LBK. 2 Bedrooms 1 Bath On 2nd Floor NO HURRICANE DAMAGE
    From $188 per night (USD)

    Expedia

    Private home, North End LBK. 2 Bedrooms 1 Bath On 2nd Floor NO HURRICANE DAMAGE

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Private Beach Cottage with apartment on second floor. Top floor apartment has two bedrooms, one bath, Living Room and Ea ...

    From $188 per night (USD)

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    Details
  • Best views of the beach from your balcony Unit 301
    From $417 per night (USD)

    VRBO

    Best views of the beach from your balcony Unit 301

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Paradise! Unit 301 with unobstructed Mexican Gulf View. This is a corner condo, so you have more space and a ...

    From $417 per night (USD)

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    Details
  • Cedars East #603 Townhome by RVA
    From $299 per night (USD)

    Expedia

    Cedars East #603 Townhome by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...

    From $299 per night (USD)

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    Details
  • Arbomar 302 Gulf Front 2 BR by FVC
    From $232 per night (USD)

    VRBO

    Arbomar 302 Gulf Front 2 BR by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beachfront Bliss on Longboat Key – Stunning Views & Modern Comfort Stay directly on the beach in this beautifully upd ...

    From $232 per night (USD)

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    Details
  • Newly Renovated - 2BR Beachfront Condo by FVC
    From $387 per night (USD)

    Expedia

    Newly Renovated - 2BR Beachfront Condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    NEWLY RENOVATED!! A beachfront condominium managed by Florida Vacation Connection is located on the world-renowned Long ...

    From $387 per night (USD)

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    Details
  • Beachview 2 BR \/ 2 BA Beachplace condo by FVC
    From $253 per night (USD)

    VRBO

    Beachview 2 BR \/ 2 BA Beachplace condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Offered by FL Vacation Connection, Beachplace is a wonderful community known for its beautifully manicured grounds, outs ...

    From $253 per night (USD)

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    Details
  • Experience a resort feel vacation on the beach in Longboat Key
    From $305 per night (USD)

    Expedia

    Experience a resort feel vacation on the beach in Longboat Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Two bedrooms, two baths, (approximately 1500 square feet) with a study, two balconies, an assigned covered parking , loc ...

    From $305 per night (USD)

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    Details
  • Unit #208 Sand Cay Beach Resort Pool and Garden View
    From $414 per night (USD)

    VRBO

    Unit #208 Sand Cay Beach Resort Pool and Garden View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you ...

    From $414 per night (USD)

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    Details
  • Beachplace 7-102 Condo by RVA
    From $333 per night (USD)

    Expedia

    Beachplace 7-102 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Beachplace 7-102, a nicely decorated two-bedroom, two-bath unit at Beachplace that includes direct, private w ...

    From $333 per night (USD)

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    Details
  • Beachfront With Incredible Panoramic Gulf View and The Most Beautiful Sunset.
    From $380 per night (USD)

    VRBO

    Beachfront With Incredible Panoramic Gulf View and The Most Beautiful Sunset.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    NO HURRICANE HELENE AND MILTON DAMAGES! BEACH IS OPEN. POOL IS CLEANED, UP AND RUNNING. GROUND AREA IS CLEANED. WE ARE ...

    From $380 per night (USD)

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    Details
  • ON the Beach, 2nd Floor \nNOTE: DUE TO HURRICANES, THE ELEVATOR IS NOT WORKING.
    From $379 per night (USD)

    Expedia

    ON the Beach, 2nd Floor \nNOTE: DUE TO HURRICANES, THE ELEVATOR IS NOT WORKING.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    On the Beach - Full view of the Gulf of Mexico. Fully furnished and equipped. Includes Long Distance phone service wit ...

    From $379 per night (USD)

    Expedia

    Details
  • \Discover Your Coastal Oasis  in Longboat Key, FL\  and St. Armands Area
    From $329 per night (USD)

    VRBO

    \"Discover Your Coastal Oasis in Longboat Key, FL\" and St. Armands Area

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stunning one bedroom one bath unit with just a short walk to Longboat Key Beach(Across the Street). Come enjoy beautiful ...

    From $329 per night (USD)

    VRBO

    Details
  • La Playa #203D Luxury Condo by RVA
    From $1762 per night (USD)

    Expedia

    La Playa #203D Luxury Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to La Playa #203D by RVA. Step out your door to the white sandy beach and emerald waters of the Gulf of Mexico. ...

    From $1762 per night (USD)

    Expedia

    Details
  • Beautiful 2\/2 bay veiw unit!! Fall dates are filling up quick, book yours today!
    From $289 per night (USD)

    VRBO

    Beautiful 2\/2 bay veiw unit!! Fall dates are filling up quick, book yours today!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Due to Hurricane Helene, our properties are still recovering and updating until further notice. Harbor Villa Club is no ...

    From $289 per night (USD)

    VRBO

    Details
  • Take a Peek at a fabulous unit. On Sale, Jan 9- to 25, then booked late April
    From $364 per night (USD)

    Expedia

    Take a Peek at a fabulous unit. On Sale, Jan 9- to 25, then booked late April

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full ki ...

    From $364 per night (USD)

    Expedia

    Details
  • Client texted said View Last minute cancel Feb 8-15
    From $364 per night (USD)

    VRBO

    Client texted said View Last minute cancel Feb 8-15

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full ki ...

    From $364 per night (USD)

    VRBO

    Details
  • Beachplace 5-301 Condo by RVA
    From $238 per night (USD)

    Expedia

    Beachplace 5-301 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RVA proudly presents an exquisite two-bedroom, two-bathroom residence nestled in building 5, offering unparalleled Gulf ...

    From $238 per night (USD)

    Expedia

    Details
  • NO REGRETS -Bright beautiful sunny home. Elevator beside driveway to upstairs.
    From $597 per night (USD)

    VRBO

    NO REGRETS -Bright beautiful sunny home. Elevator beside driveway to upstairs.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    8

    We have a private laneway to our own piece of beautiful sugar sand, longboat key beach. We adjoin 35 acres of park and ...

    From $597 per night (USD)

    VRBO

    Details
  • Cabana Beach Club #2 Resort by RVA
    From $638 per night (USD)

    Expedia

    Cabana Beach Club #2 Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key islan ...

    From $638 per night (USD)

    Expedia

    Details
  • Casa Del Mar Home on Longboat Key by RVA
    From $429 per night (USD)

    VRBO

    Casa Del Mar Home on Longboat Key by RVA

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy island-style vacations at the Casa del Mar Home. Located on the north end of the exclusive island of Longboat Key, ...

    From $429 per night (USD)

    VRBO

    Details
  • Cedars East #528 Townhome by RVA
    From $308 per night (USD)

    Expedia

    Cedars East #528 Townhome by RVA

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...

    From $308 per night (USD)

    Expedia

    Details
  • Silver Sands #234 Resort by RVA
    From $253 per night (USD)

    VRBO

    Silver Sands #234 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...

    From $253 per night (USD)

    VRBO

    Details
  • Walk to Beach\/Bay, 1st Floor, Beach Castle #23
    From $417 per night (USD)

    Expedia

    Walk to Beach\/Bay, 1st Floor, Beach Castle #23

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Relax in this privately owned and “coastal themed” ground floor condo that sleeps 4 with bay views from the privacy of y ...

    From $417 per night (USD)

    Expedia

    Details
  • Silver Sands #245 Resort by RVA
    From $363 per night (USD)

    VRBO

    Silver Sands #245 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...

    From $363 per night (USD)

    VRBO

    Details
  • Silver Sands #255S Resort by RVA
    From $427 per night (USD)

    Expedia

    Silver Sands #255S Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...

    From $427 per night (USD)

    Expedia

    Details
  • Beach Castle Resort #1 by RVA
    From $607 per night (USD)

    VRBO

    Beach Castle Resort #1 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to laun ...

    From $607 per night (USD)

    VRBO

    Details
  • Silver Sands #235 Resort by RVA
    From $383 per night (USD)

    Expedia

    Silver Sands #235 Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...

    From $383 per night (USD)

    Expedia

    Details
  • Cabana Beach Club #7 Resort by RVA
    From $497 per night (USD)

    VRBO

    Cabana Beach Club #7 Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key islan ...

    From $497 per night (USD)

    VRBO

    Details
  • Silver Sands #241 Resort by RVA
    From $341 per night (USD)

    Expedia

    Silver Sands #241 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...

    From $341 per night (USD)

    Expedia

    Details
  • Cedars East #810 Townhome by RVA
    From $343 per night (USD)

    VRBO

    Cedars East #810 Townhome by RVA

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    7

    RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...

    From $343 per night (USD)

    VRBO

    Details
  • Outrigger Resort #8 Condo by RVA
    From $367 per night (USD)

    Expedia

    Outrigger Resort #8 Condo by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger ...

    From $367 per night (USD)

    Expedia

    Details
  • Silver Sands #232 Resort by RVA
    From $302 per night (USD)

    VRBO

    Silver Sands #232 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...

    From $302 per night (USD)

    VRBO

    Details
  • Tarawitt Home on Longboat Key by RVA
    From $238 per night (USD)

    Expedia

    Tarawitt Home on Longboat Key by RVA

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    RVA presents this spacious vacation home. The Tarawitt Home, is located on a secluded road at the northern tip of Longbo ...

    From $238 per night (USD)

    Expedia

    Details
  • Island Paradise: House on Longboat Key by RVA
    From $259 per night (USD)

    VRBO

    Island Paradise: House on Longboat Key by RVA

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    RVA features a relaxing, serene home beautifully furnished and ready for you to enjoy Longboat Key's sunshine. This home ...

    From $259 per night (USD)

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    Details
  • Silver Sands #252 Resort by RVA
    From $345 per night (USD)

    Expedia

    Silver Sands #252 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...

    From $345 per night (USD)

    Expedia

    Details
  • Cabana Beach Club #5 Resort by RVA
    From $334 per night (USD)

    VRBO

    Cabana Beach Club #5 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key islan ...

    From $334 per night (USD)

    VRBO

    Details
  • Beach Castle Resort #3 by RVA
    From $587 per night (USD)

    Expedia

    Beach Castle Resort #3 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to laun ...

    From $587 per night (USD)

    Expedia

    Details