Holmes Beach, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Holmes Beach, Florida on RentalSaver.com!

Holmes Beach Rentals

From $452 per night (USD)
VRBO
Beautiful cottage just around the corner from the beach with Private Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Seahorse Beach House located just a few houses from the Gulf beaches of Anna Maria Island. Seahorse Beach Hou ...
From $452 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Ground Floor Cottage with 2 Master Suites and Private Heated Pool - Close to Beach!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Castaway Cottage located 2 houses down from the Gulf beaches of Anna Maria Island. Castaway Cottage is a grou ...
From $408 per night (USD)
Expedia
From $259 per night (USD)
VRBO
Heated Pool & Spa FREE WiFi & Trolley, Close to Beach & Bay with Dock on the...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
**ASK ABOUT LAST-MINUTE DEALS! We at Beachrentals.mobi LOVE Sunbow Bay for its awesome amenities and afford ...
From $259 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Two Bedroom Ground Floor Island Home Sleeps 5 and Includes Heated Pool.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to the Sand Dollar Shack located just a few houses from the Gulf beaches on Anna Maria Island. The Sand Dollar S ...
From $452 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Cove At Sandy Point 208 Overlooking Natural Preserve With A Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRC19-000217 Unit 208 is a two-bedroom, two-bathroom condo located at the Cove at Sandy Pointe. Under new ownership, ma ...
From $262 per night (USD)
VRBO
From $362 per night (USD)
Expedia
MI Happy Place Sea Horse 3 | Beach Across St | Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
VRC19-000207 Newly renovated in late 2024, this 2BR/1BA retreat features a brand-new kitchen with granite counter tops, ...
From $362 per night (USD)
Expedia
From $289 per night (USD)
VRBO
MI Happy Place Sea Turtle 4 | Beach Across St | Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
VRC19-000208 Fully renovated in late 2024, this 2BR/1BA coastal retreat features a brand-new kitchen with granite count ...
From $289 per night (USD)
VRBO
Click For Pricing
Expedia
Two bedroom private heated pool and hot tub, on AMI- pet friendly!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Island Delight is a cozy 2 bedroom one bath duplex with a private heated saltwater pool and hot tub in the Seaside Garde ...
Click For Pricing
Expedia
From $1196 per night (USD)
VRBO
Tiki a Gulf-Front Escape with Unmatched Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC16-000568 Tiki | Gulf-Front Escape with Unmatched Views Your Private Slice of Paradise Awaits! Perched directly on ...
From $1196 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Cozy Cottage for 4 located steps from the beach. Heated Pool in private Patio.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Yellowfin Cottage located just 2 houses from the Gulf beaches on Anna Maria Island. Yellowfin Cottage is a gr ...
From $464 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Coastal cute on Anna Maria Island, 2 bedroom with private pool! Pet friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
4
Coral Breeze (Units A and B) is your new paradise. Each 2 bedroom 2 bath side of this adorable duplex features everythin ...
From $465 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Perfect island getaway for families! Private pool, close to the beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coconut Cottage #3 by Anna Maria Island Locals Condo in Holmes Beach, FL Located across the street from the Manatee Pub ...
From $395 per night (USD)
Expedia
From $480 per night (USD)
VRBO
Casa Sierra 203A - 2BR Condo with Pool By Island Real Estate Vacations
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This small quiet complex is just a two minute walk to the beautiful white sand beach. A ground level unit, find an outdo ...
From $480 per night (USD)
VRBO
$A Wright Place 2\/2 Private Pool Duplex Short Block To Beautiful Beaches$
From $323 per night (USD)
Expedia
A Wright Place 2\/2 Private Pool Duplex Short Block To Beautiful Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC16-000511 A Wright Place, located at 6803 Holmes Blvd., is a comfortable two bedroom, two bath duplex with poolside ...
From $323 per night (USD)
Expedia
From $916 per night (USD)
VRBO
Breakers 1 | A Classic Old Florida Beach Cottage – Fully Restored
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Some homes are more than just a place to stay—they hold a story. Breakers 1 is one of the few remaining Old Florida coas ...
From $916 per night (USD)
VRBO
From $569 per night (USD)
Expedia
3 bedroom, luxury beach house on Anna Maria Island, private pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Palm Villa welcomes you to sunny AMI! Palm Villa is a very comfortable, casual, but well-appointed Florida island getawa ...
From $569 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Holmes Beach Cottage Steps to the Beach with Heated Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to the Starfish Shack located just a few houses from the Gulf beaches of Anna Maria Island. The Starfish Shack i ...
From $452 per night (USD)
VRBO
From $440 per night (USD)
Expedia
SS Salamander South | Steps to the Beach + Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
VRC16-000500 Your Holmes Beach Escape Awaits Tucked just one block from the pristine Gulf beaches, SS Salamander South ...
From $440 per night (USD)
Expedia
$Peace N Paradise Private Relaxing Pool\/Spa 300 Yards To White Sandy Beach$
From $426 per night (USD)
VRBO
Peace N Paradise Private Relaxing Pool\/Spa 300 Yards To White Sandy Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC20-000280 Peace 'n Paradise, located at 5405 B Gulf Drive in Holmes Beach is a comfortable two bedroom, two bath dup ...
From $426 per night (USD)
VRBO
$Sea Pirate 3 Attractive 2\/1 Condo With Pool Just Steps To Beach$
From $346 per night (USD)
Expedia
Sea Pirate 3 Attractive 2\/1 Condo With Pool Just Steps To Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
VRC16-000556 Sea Pirate Condo #3, located at 3303 Gulf Drive in the heart of Holmes Beach is just across the street fro ...
From $346 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Island Cottage with open living area, pool, ground floor very close to beach located in Holmes Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Bluefin Cottage located a few houses from the Gulf beaches of Anna Maria Island. Bluefin Cottage is a half d ...
From $445 per night (USD)
VRBO
From $299 per night (USD)
Expedia
MI Happy Place Sand Dollar 2 | Beach Across St | Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
VRC19-000210 Fully renovated in late 2024, this 2BR/1BA retreat now features a brand-new kitchen with granite counter t ...
From $299 per night (USD)
Expedia
$Gulf Sands 201 2\/2 Condo Gulf Front With Large Pool$
From $452 per night (USD)
VRBO
Gulf Sands 201 2\/2 Condo Gulf Front With Large Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRC16-000492 *DUE TO HURRICANES THE ELEVATOR AT THIS PROPERTY IS OUT OF SERVICE AT THIS TIME Gulfsands Condo #201, loca ...
From $452 per night (USD)
VRBO
$Fountainhead Condo 4 2\/2 Condo Steps To white Sugar Sand Beach, Large Pool$
From $237 per night (USD)
Expedia
Fountainhead Condo 4 2\/2 Condo Steps To white Sugar Sand Beach, Large Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
VRC16-000542 Fountainhead Condo #4, located at 3402 6th Avenue in Holmes Beach only a few steps from the beautiful beac ...
From $237 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Anna Maria Beach Place 6 Directly Across The Street From The Beach With Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
VRC 21-000063 Anna Maria Beach Place 6 is thoroughly cleaned and sanitized prior to your arrival. We pay special attent ...
From $333 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Two Bedroom Cottage with Tropical Landscaping Surrounding Private Heated Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Surf Camp Cottage located just 3 houses down from the Gulf beaches of Anna Maria Island. Surf Camp Cottage is ...
From $421 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Ground Floor home for 5, short walk to beach and private heated pool! Lovely open living area
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Citrus Cottage located steps from the Gulf beaches of Anna Maria Island. Citrus Cottage is a ground level hal ...
From $408 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Palm Cay 5, Newly Remodeled Townhome Steps from the Beach. Heated Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC16-000555 The New Pictures Are Coming Very Soon!! Palm Cay 5 | Newly Remodeled Townhome Steps from the Beach Freshly ...
From $436 per night (USD)
Expedia
From $453 per night (USD)
VRBO
Seaside Beach House 101 Gulf Front Condo Pool Unforgettable Sunset Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
VRC16-000502 Seaside Beach House #101 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a ...
From $453 per night (USD)
VRBO
$GULF BEACH WALK OUT 3 BED\/2 BATH, Heated Pool, FREE WiFi & Trolley, A Rare...$
From $775 per night (USD)
Expedia
GULF BEACH WALK OUT 3 BED\/2 BATH, Heated Pool, FREE WiFi & Trolley, A Rare...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**ASK ABOUT LAST MINUTE DEALS! This direct Gulf-front property is sure to be a hit! It has been completely ...
From $775 per night (USD)
Expedia
From $548 per night (USD)
VRBO
Seaside Beach House 105 Gulf Front Condo Pool Unforgettable Sunset Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
VRC16-000506 You will enjoy this gulf front condominium on Florida's Anna Maria Island. This is a smoke free two-bedroo ...
From $548 per night (USD)
VRBO
From $1239 per night (USD)
Expedia
Beautiful Island Home with Great Amenities, Pool, Grill, located close to the Gulf Beaches
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to Coconut Hideaway located just steps away from the Gulf beaches of Anna Maria Island. This beach house has a p ...
From $1239 per night (USD)
Expedia
From $507 per night (USD)
VRBO
3 bedroom home on Anna Maria Island, private heated pool, super location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This stunning tropical oasis called Sunbreeze features hardwood and tile floors throughout the home, front and back deck ...
From $507 per night (USD)
VRBO
From $1040 per night (USD)
Expedia
Luxury Four Bedroom Home with Easy Access to Beach. Pool and private Patio.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to Aqua Oasis located just steps from the Gulf beaches of Anna Maria Island. This beach house has a private pati ...
From $1040 per night (USD)
Expedia
$Bradenton Beach Club unit D | 3\/2 Beach Front Condo$
From $857 per night (USD)
VRBO
Bradenton Beach Club unit D | 3\/2 Beach Front Condo
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*DUE TO HURRICANES THE ELEVATOR AT THIS PROPERTY IS OUT OF SERVICE AT THIS TIME Welcome to your dream getaway – a stunn ...
From $857 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Ground Floor Two Bedroom Island Styled Home on Beautiful Anna Maria. Close to Beaches!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Groovy Gecko Cottage just a few houses down from the Gulf beaches of Anna Maria Island. This cottage is a gro ...
From $452 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Coastal cute on Anna Maria Island, 2 bedroom with private pool! Pet friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
4
Coral Breeze (Units A and B) is your new paradise. Each 2 bedroom 2 bath side of this adorable duplex features everythin ...
From $465 per night (USD)
VRBO
From $346 per night (USD)
Expedia
MI Happy Place Sand Castle1 Beach Across St & Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
VRC19-000209 Your Relaxing Getaway on Anna Maria Island Freshly renovated in late 2024, MI Happy Place Sand Castle 1 no ...
From $346 per night (USD)
Expedia
From $1117 per night (USD)
VRBO
Absolutely Perfect Private Beach Front Pool Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
VRC16-000512 Absolutely Perfect is thoroughly cleaned and sanitized prior to your arrival. We pay special attention ...
From $1117 per night (USD)
VRBO
From $1212 per night (USD)
Expedia
Valhalla Both Units Duplex On Beach Covered Deck Unforgettable Sunsets
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
VRC's 16-000569 & VRC 16-000570 The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three ba ...
From $1212 per night (USD)
Expedia
$Sandy Point 109 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...$
From $277 per night (USD)
VRBO
Sandy Point 109 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sandy Point 109 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC19-000084 Distan ...
From $277 per night (USD)
VRBO
From $492 per night (USD)
Expedia
Royal Palm: Pool, 2 Blocks to Beach, Close to Dining & Shopping by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Royal Palm by Anna Maria Life Vacation Rentals 5701 Holmes Blvd, Unit A, Holmes Beach, FL 34217 What You'll Love About ...
From $492 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Tiki Cottage: 2.5 Blocks to Beach, Pool with Swim up Tiki Bar by Anna Maria Live Vacation Rentals
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Tiki Cottage by Anna Maria Life Vacation Rentals 303 64th St, Unit B, Holmes Beach, FL 34217 2.5 Blocks to the Beach! ...
From $568 per night (USD)
VRBO
From $591 per night (USD)
Expedia
Happy Place: 1.5 Blocks to Beach, Pool Home, Florida Room by Anna Maria Life Vacation Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Happy Place by Anna Maria Life Vacation Rentals 210 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: L ...
From $591 per night (USD)
Expedia
From $340 per night (USD)
VRBO
Castnetter Beach Resort 5
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protec ...
From $340 per night (USD)
VRBO
From $547 per night (USD)
Expedia
Chiki Tiki West: Eclectic Beach House, Tiki Bar & Pool, 2.5 Blocks to Beach by Anna Maria Life
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Chiki Tiki West by Anna Maria Life Vacation Rentals 303 64th St, Unit A, Holmes Beach, FL 34217 What You'll Love About ...
From $547 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Casa Sierra 203B - 2BR Condo with Pool - By Island Real Estate Vacations
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Casa Sierra Resort is a private Mediterranean style four unit complex in Holmes Beach on beautiful Anna Maria Island. Th ...
From $385 per night (USD)
VRBO
$Coconuts108 - GULFFRONT - 1BR\/1BA with pool - By Island Real Estate Vacations$
From $533 per night (USD)
Expedia
Coconuts108 - GULFFRONT - 1BR\/1BA with pool - By Island Real Estate Vacations
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
“The Coconuts Beach Resort 108” is a 1 bed 1 bath beach front condo, nestled in the heart of Holmes Beach. Apart of the ...
From $533 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Chapter 2: Renovated pool home, tiki hut and close to beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Chapter 2 Create some magic memories in a slice of “Old Florida”. Relax outside in the heated saltwater p ...
From $375 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Adorable cottage just across the street from the beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Coconut Cottage #2 By AMI Locals Condo in Holmes Beach, FL Located across the street from the Manatee Public Beach! Hi ...
From $371 per night (USD)
Expedia
From $603 per night (USD)
VRBO
🌴”Kiwi Cottage at Holmes Beach” - Private Heated Pool +Spa+Walk to the Beach! 🌞
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Kiwi Coastal Cottage is under new ownership and every space has been thoughtfully redecorated with a cozy coastal island ...
From $603 per night (USD)
VRBO
From $858 per night (USD)
Expedia
Island Retreat- Stunning 4 bedroom with private heated pool and walk to beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
At A Glance Luxury Island style home Two minute stroll to the beach Tropical heated pool/Tiki Bar West-facing, view of ...
From $858 per night (USD)
Expedia
From $1062 per night (USD)
VRBO
Blue Water View- 6 bedrooms with amazing rooftop deck and private heated pool
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
At A Glance On our Professional Linen Service Program Beautiful Gulf water views, only 1 minute walk to the beach-locat ...
From $1062 per night (USD)
VRBO
From $1157 per night (USD)
Expedia
Pool and Beach Access: Ultimate Friends Getaway! - Coconuts Gulf View #117
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coconuts Gulf View #117 by AMI Locals Condo in Holmes Beach, FL Coconuts Gulf View #117 is the ultimate spot for a fri ...
From $1157 per night (USD)
Expedia
From $1169 per night (USD)
VRBO
Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
A Pirate’s Dream by AMI Locals Home in Holmes Beach, Florida This grand, waterfront, four-bedroom, and three-and-a-ha ...
From $1169 per night (USD)
VRBO
From $815 per night (USD)
Expedia
2nd floor Condo with Beach and Pool Access - Coconuts Gulf View #118
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coconuts Gulf Views #118 by AMI Locals Condo in Holmes Beach, Florida VRC21-000172 Let the good times roll at Coconu ...
From $815 per night (USD)
Expedia
$Lakeside Beach House 3\/2 Pool Home Outdoor Kitchen Close to Beach$
From $527 per night (USD)
VRBO
Lakeside Beach House 3\/2 Pool Home Outdoor Kitchen Close to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC16-000807 The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private heated ...
From $527 per night (USD)
VRBO
From $362 per night (USD)
Expedia
A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly furnished ground level home is ...
From $362 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Vibrant retreat with pool, beach access, tennis, balcony, & stunning ocean views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Place 19 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $533 per night (USD)
VRBO
$BEACH FRONT, 2 Bd\/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets$
From $476 per night (USD)
Expedia
BEACH FRONT, 2 Bd\/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
**ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom ...
From $476 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Water-view condo near the beach with pools, dock, pickleball - dog-friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $240 per night (USD)
VRBO
From $703 per night (USD)
Expedia
Beachfront - Sandy Turtle by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers pictures ...
From $703 per night (USD)
Expedia
From $774 per night (USD)
VRBO
Gulf Front 1 Bedroom Condo - Amazing Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Coconuts Beachfront #112 Condo in Holmes Beach, Florida VRC21-000175 Your dream beach vacation awaits at Coconuts Beach ...
From $774 per night (USD)
VRBO
$Mango Bay – Luxury 4BR w\/ Heated Pool, Spa & Game Room$
From $871 per night (USD)
Expedia
Mango Bay – Luxury 4BR w\/ Heated Pool, Spa & Game Room
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) 3,000 sqft of a Beautifully Restored Island Home with Poo ...
From $871 per night (USD)
Expedia
From $1045 per night (USD)
VRBO
Golf Cart, Salty Shamrock by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be ov ...
From $1045 per night (USD)
VRBO
$WBC 212 Spacious 2\/2 Pool Tennis Condo Close To White Sand Beach Shopping$
From $231 per night (USD)
Expedia
WBC 212 Spacious 2\/2 Pool Tennis Condo Close To White Sand Beach Shopping
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRC20-000174 Westbay Cove 212 located at 600 Manatee Ave West in Holmes Beach is a picturesque and luxurious two bedroo ...
From $231 per night (USD)
Expedia
From $567 per night (USD)
VRBO
FANTASTIC, RENOVATED 2 BEDROOM HOME STEPS TO BEACH!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3706 Gulf Drive, Holmes Beach, FL Anna Maria Island Fantastic, recently renovated home located just steps to the beach. ...
From $567 per night (USD)
VRBO
$Island Beach Club 24 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...$
From $392 per night (USD)
Expedia
Island Beach Club 24 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Beach Club 24 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. VRC16-000069 Max 1 veh ...
From $392 per night (USD)
Expedia
$Island Beach Club 1- Anna Maria Island-Condo 2 Bedroom\/2 Bath gulf front,...$
From $520 per night (USD)
VRBO
Island Beach Club 1- Anna Maria Island-Condo 2 Bedroom\/2 Bath gulf front,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Beach Club 1 - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC16-000745 Beach/Gulf Front - Com ...
From $520 per night (USD)
VRBO
From $663 per night (USD)
Expedia
AM I Dreaming: Heated Pool, Family Friendly Home, 3-min walk to beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The vacation you have imagined finally becomes a reality. AM I dreaming is a bright and charming 3 bedroom, 2 bathroom c ...
From $663 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Sun Plaza West 105 - Two Bedroom condo, Sleeps 6- on the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AT A GLANCE Recently remodeled gulf front condo 2 Bedrooms and 2 Bathrooms with two balconies Complex equipped with a l ...
From $448 per night (USD)
VRBO
$217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...$
From $254 per night (USD)
Expedia
217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC#20-000113 Private Poo ...
From $254 per night (USD)
Expedia
$Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...$
From $402 per night (USD)
VRBO
Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom / 1 Bath, maximum occupancy of 4 people. VRC20-000254 ...
From $402 per night (USD)
VRBO
$Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide$
From $1127 per night (USD)
Expedia
Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Sands of Time 6908 Holmes Blvd Holmes Beach, FL 34217 Sands of Time is a newly built 6 bedroom, 4.5 bathroom vacation ...
From $1127 per night (USD)
Expedia
$Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath gulf...$
From $489 per night (USD)
VRBO
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath gulf...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Gulf/Beach Fr ...
From $489 per night (USD)
VRBO
From $169 per night (USD)
Expedia
White Palm-2 bedroom monthly condo getaway awaits you with beautiful bay views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
At a Glance Newly redecorated condo located on the northeastern Bayfront of Anna Maria Island 2 bedrooms and 2 bathro ...
From $169 per night (USD)
Expedia
From $890 per night (USD)
VRBO
Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66t ...
From $890 per night (USD)
VRBO
$Sandy Point 111 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...$
From $241 per night (USD)
Expedia
Sandy Point 111 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sandy Point 111 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000289 Distan ...
From $241 per night (USD)
Expedia
$Sandy Point Cove 112 - Anna Maria Island -Condo 2 Bedroom\/ 2 Bath, maximum...$
From $318 per night (USD)
VRBO
Sandy Point Cove 112 - Anna Maria Island -Condo 2 Bedroom\/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sandy Point Cove 112 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC19-000138 Distance ...
From $318 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Cuddlefish Cove: Heated Pool, rooftop deck, gorgeous views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cuddlefish Cove Your flip flops have found a new retreat by the beach! Stay for a week or a month at this dazzling Key W ...
From $495 per night (USD)
Expedia
From $734 per night (USD)
VRBO
Casa Morado-Pet Friendly Pool Home West of Gulf Dr-By Island Real Estate Vacatio
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Just a few short blocks with no busy roads to cross to get to the beach. The home is very spacious with 4 bedrooms. Th ...
From $734 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Anna Maria Island Sunshine Kiss Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Sunshine Kissed Villa has everything you need for a complete holiday! Our villa has all you need for staying in, an ...
From $250 per night (USD)
VRBO
$Anna Maria Island \Star Fish\Condo & Boat Slip-2BR-2BA-Sleeps4$
From $217 per night (USD)
VRBO
Anna Maria Island \"Star Fish\"Condo & Boat Slip-2BR-2BA-Sleeps4
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Starfish Condo on Anna Maria Island -2 BR 2 BA With a 25' Boat Slip Wonderful quiet residential area overlooks pool; bey ...
From $217 per night (USD)
VRBO
$Sandy Point 114 - Anna Maria Island -Townhouse 3 Bedroom\/ 3 Bath, maximum...$
From $372 per night (USD)
Expedia
Sandy Point 114 - Anna Maria Island -Townhouse 3 Bedroom\/ 3 Bath, maximum...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sandy Pointe 114 - Anna Maria Island - Townhouse 3 Bedroom/ 3 Bath, maximum occupancy of 6 people. VRC16-000070 Di ...
From $372 per night (USD)
Expedia
From $1184 per night (USD)
VRBO
Silver Surf- A stunning family home 2 blocks from the beach.
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
The minute you walk in the front door at Silver Surf you'll be convinced that you're about to experience the very best o ...
From $1184 per night (USD)
VRBO
From $905 per night (USD)
Expedia
For Shore: Sleeps 10, steps to beach, heated pool!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
If you are hoping to stay on the perfect Old Florida island in the perfect beach home, you have found your destination a ...
From $905 per night (USD)
Expedia
From $717 per night (USD)
VRBO
GORGEOUS 3 BEDROOM POOL HOME JUST STEPS TO BEACH
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Two For Sea ... Light and bright, beautifully decorated 3 bedroom, 3 bath newer home located in the city of Holmes Beac ...
From $717 per night (USD)
VRBO
$Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...$
From $412 per night (USD)
Expedia
Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Walk 313 - Anna Maria Island - Townhouse - 3 Bedroom/ 2 .5 Bath, maximum occupancy of 6 people. VRC16-000052 ...
From $412 per night (USD)
Expedia
$510 Bayview - Anna Maria Island - Private home 5 Bedroom \/ 5 Bath with...$
From $1049 per night (USD)
VRBO
510 Bayview - Anna Maria Island - Private home 5 Bedroom \/ 5 Bath with...
Bedrooms:
5
Bathrooms:
5
Sleeps:
6
510 Bayview - Anna Maria Island - 5 Bedroom / 5 Bath, maximum occupancy of 6 people. Canal Home - Private Pool - ...
From $1049 per night (USD)
VRBO
$Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...$
From $303 per night (USD)
Expedia
Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sandy Point 205 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000291 Distan ...
From $303 per night (USD)
Expedia
$LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath , maximum...$
From $353 per night (USD)
VRBO
LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath , maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC19-000138 Community ...
From $353 per night (USD)
VRBO
Click For Pricing
Expedia
Beach Bay Serenity: Pine Ave canal front pool home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you enjoy salt air and sea breezes, morning coffee on your patio, walking miles and miles of white sandy beach and sw ...
Click For Pricing
Expedia
From $430 per night (USD)
VRBO
Seaside Beach House 203 | Gulf-Front Escape with Panoramic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
VRC20-000296 Wake up to breathtaking Gulf views and fall asleep to the sound of the waves at Seaside Beach House 203, a ...
From $430 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sea La Vie by Anna Maria Life Vacation Rentals 205 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: Lo ...
From $533 per night (USD)
Expedia
From $667 per night (USD)
VRBO
Florida Breeze: Pool home in perfect central location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Florida Breeze is the perfect vacation rental for your next trip to Anna Maria Island! The location with the short walk ...
From $667 per night (USD)
VRBO
From $337 per night (USD)
Expedia
(2) Bedroom (2) Bath with Private 10' x 30' Sun Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Anna Maria Island's "Castnetter 5" is a delightful Island local located directly across the street from the seven acre " ...
From $337 per night (USD)
Expedia
From $1685 per night (USD)
VRBO
ISLAND LIFE VILLA is Luxury at it's Finest! Incredible Water Views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
*During high season, we currently rent Saturday – Saturday. Please adjust your date range or contact our reservations of ...
From $1685 per night (USD)
VRBO
$Turtle Nest! New Holiday House w\/ Pool, Wifi, and Access to the Beach$
From $595 per night (USD)
VRBO
Turtle Nest! New Holiday House w\/ Pool, Wifi, and Access to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Remodeled in 2025, this comfortable and tastefully furnished home offers everything you need for a relaxed vacation with ...
From $595 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Home with Private Outdoor Living Space, Community Pool - Sea La Vie
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea La Vie by AMI Locals Condo in Holmes Beach, Florida VRC21-000203 Welcome to Sea La Vie! This three-bedroom, three- ...
From $382 per night (USD)
VRBO
From $606 per night (USD)
Expedia
Charming Private Home, Private Pool and Spa. Fenced Yard, Updates Throughout
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Seahorse Cottage by AMI Locals Home in Holmes, Beach Florida VRC16-000110 Enjoy a luxury vacation with friends and fami ...
From $606 per night (USD)
Expedia

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