Holmes Beach Rentals
- From $946 per night (USD)
VRBO
Golf Cart included, 3 houses from the beach with private heated pool & spa
- 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 $946 per night (USD)VRBO
- Click For Pricing
Expedia
Coconut Breeze by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coconut Breeze is a beautifully renovated duplex only a short five-minute walk to the beach. Coconut Breeze is finished ...
Click For PricingExpedia
- From $268 per night (USD)
VRBO
Island Beach Club 1 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Beach Club 1 - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC16-000745Beach/Gulf Front - Community ...
From $268 per night (USD)VRBO
- From $494 per night (USD)
Expedia
BAY PALMS - SPACIOUS POOL HOME WITH WONDERFUL AMENITIES. WALK TO A GREAT BEACH! A MUST SEE!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Palms..... Exceptional, newer 3 bedroom, 2.5 bath villa located just a short walk to the beach. This wonderful renta ...
From $494 per night (USD)Expedia
- From $488 per night (USD)
VRBO
AM I Dreaming: 3 BR, 2 BA House in Holmes Beach, Sleeps 6
- 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 $488 per night (USD)VRBO
- From $325 per night (USD)
Expedia
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 $325 per night (USD)Expedia
- From $222 per night (USD)
VRBO
217 84th Street in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC#20-000113Private Pool - Dis ...
From $222 per night (USD)VRBO
- From $268 per night (USD)
Expedia
Island Beach Club 22
- 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 $268 per night (USD)Expedia
- Click For Pricing
VRBO
LIME IN DE COCONUT- DOWNSTAIRS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
LIME IN DE COCONUT- DOWNSTAIRS..... Adorable, ground level two bedroom, two bath in a 2 unit cottage. Cheery beach de ...
Click For PricingVRBO
- Click For Pricing
Expedia
WONDERFUL TOWNHOME WITH VIEWS OF THE GULF! 2 BEDROOM, 2.5 BATH WITH HEATED POOL AND EASY WALK TO TH
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE SANDY OWL AT HOLMES BEACH Part of the Beach Townhouses complex, #107 The Sandy Owl sits directly across from Manatee ...
Click For PricingExpedia
- From $400 per night (USD)
VRBO
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 $400 per night (USD)VRBO
- Click For Pricing
Expedia
3011 Ave E-2 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
3011 Avenue E, Unit 2 - Anna Maria Island - Triplex Condo 2 Bedroom/ 2 Bath ground floor, maximum occupancy of 6 people. ...
Click For PricingExpedia
- From $268 per night (USD)
VRBO
Island Beach Club 21
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC16-000067 ...
From $268 per night (USD)VRBO
- 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 $391 per night (USD)
VRBO
FANTASTIC, RENOVATED 2 BEDROOM HOME STEPS TO BEACH!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
3706 Gulf Drive, Holmes Beach, FL Anna Maria Island Fantastic, recently renovated home located just steps to the beach. ...
From $391 per night (USD)VRBO
- From $268 per night (USD)
Expedia
Island Beach Club 24
- 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 $268 per night (USD)Expedia
- From $240 per night (USD)
VRBO
Restored 1920's Anna Maria Island Cottage . 1 block to the beach with no roads to cross! Quaint, ch
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
110 31st St., Holmes Beach, FL 34217 "Almost to the Beach" ... Charming, updated 1920's cottage with 2 bedrooms and 1 b ...
From $240 per night (USD)VRBO
- From $124 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 $124 per night (USD)Expedia
- From $276 per night (USD)
VRBO
Sandy Point 111 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sandy Point 111 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000289 Distance to t ...
From $276 per night (USD)VRBO
- Click For Pricing
Expedia
Lime In De Coconut - Upstairs 1 bedroom, 1 bath shared pool. Walk to beaches!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
LIME IN DE COCONUT- UPSTAIRS..... Adorable, one bedroom, one bath in a 2 unit cottage. Cheery beach decor and a shared ...
Click For PricingExpedia
- From $160 per night (USD)
VRBO
Sandy Point Cove 112
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sandy Point Cove 112 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC19-000139Distance to the ...
From $160 per night (USD)VRBO
- From $554 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 $554 per night (USD)Expedia
- From $809 per night (USD)
VRBO
Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This home was lovingly updated Fall/Winter 2022-2023. New pics of the gorgeous improvements coming soon! If you are loo ...
From $809 per night (USD)VRBO
- Click For Pricing
Expedia
3011 Ave E-3 in Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
3011 Avenue E, Unit 3 - Triplex Condo 1 Bedroom/ 1 Bath, maximum occupancy of 4 people. VRC16-000051This tri-plex has a ...
Click For PricingExpedia
- From $306 per night (USD)
VRBO
313 Island Walk in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Walk 313 - Anna Maria Island - Townhouse - 3 Bedroom/ 2 .5 Bath, maximum occupancy of 6 people. VRC16-000052Priva ...
From $306 per night (USD)VRBO
- From $502 per night (USD)
Expedia
Casa Morado-Pet Friendly Pool Home West of Gulf Dr-By Island Real Estate Vacatio
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $502 per night (USD)Expedia
- From $221 per night (USD)
VRBO
Anna Maria Island Sunshine Kiss Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $221 per night (USD)VRBO
- From $219 per night (USD)
Expedia
Anna Maria Island \"Star Fish\"Condo w\/ Boat Slip- -2BR\/2BA
- 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 $219 per night (USD)Expedia
- From $236 per night (USD)
VRBO
Sandy Point Cove 114
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sandy Pointe 114 - Anna Maria Island - Townhouse 3 Bedroom/ 3 Bath, maximum occupancy of 6 people. VRC16-000070Distance ...
From $236 per night (USD)VRBO
- From $768 per night (USD)
Expedia
Silver Surf- A stunning family home 2 blocks from the beach.
- Bedrooms:
- 4
- Bathrooms:
- 5
- 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 $768 per night (USD)Expedia
- From $780 per night (USD)
VRBO
For Shore: 5 BR, 4.5 BA House in Holmes Beach, Sleeps 10
- 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 $780 per night (USD)VRBO
- From $521 per night (USD)
Expedia
GORGEOUS 3 BEDROOM POOL HOME JUST STEPS TO BEACH
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Two For Sea ... Light and bright, beautifully decorated 3 bedroom, 3 bath newer home located in the city of Holmes Beac ...
From $521 per night (USD)Expedia
- From $867 per night (USD)
VRBO
510 Bayview in Holmes Beach
- 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 $867 per night (USD)VRBO
- From $236 per night (USD)
Expedia
Sandy Point 205 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sandy Point 205 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000291 Distance to t ...
From $236 per night (USD)Expedia
- From $207 per night (USD)
VRBO
LaPlayita Condo 5 in Holmes Beach
- 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 $207 per night (USD)VRBO
- From $175 per night (USD)
Expedia
POOL HOME OPEN FOR THE SUMMER! BRING YOUR BOAT! MONTH MINIMUM - GREAT PRICE AND A GREAT LOCATION!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
239 85th Street, Holmes Beach, Anna Maria Island Bailey's Home ... Lovely and spacious 3 bedroom, 2 bath home. Recently ...
From $175 per night (USD)Expedia
- From $348 per night (USD)
VRBO
Shell Cottage- Florida style pool home close to beach.
- 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 ...
From $348 per night (USD)VRBO
- Click For Pricing
Expedia
3011 Ave E-1 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
3011 Avenue E, Unit 1 - Anna Maria Island -Triplex Condo - 4 Bedroom/ 2 Bath, maximum occupancy of 8 people. VRC16-00005 ...
Click For PricingExpedia
- From $369 per night (USD)
VRBO
Seaside Beach House 203 Gulf Front Condo Pool Unforgettable Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
VRC20-000296 This property is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high ...
From $369 per night (USD)VRBO
- From $499 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
Welcome to Sea La Vie! 205 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: Location! One Block to th ...
From $499 per night (USD)Expedia
- From $490 per night (USD)
VRBO
Florida Breeze: 3 BR, 2.5 BA House in Holmes Beach, Sleeps 6
- 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 $490 per night (USD)VRBO
- From $296 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 $296 per night (USD)Expedia
- From $612 per night (USD)
VRBO
ISLAND LIFE VILLA is Luxury at it's Finest! Incredible Water Views!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Relax. Recharge. Reconnect. Come live the Island Life at one of Anna Maria’s finest rentals designed for making magical ...
From $612 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Turtle Nest! New Holiday House w\/ Pool, Wifi, and Access to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This comfortable and tastefully furnished vacation home was built in 2012 and offers everything you need for a relaxed v ...
From $475 per night (USD)VRBO
- From $330 per night (USD)
VRBO
Refreshed townhome in the best location! Heated pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea La Vie by AMI Locals Townhome in Holmes Beach, FL Vacay mode begins when you arrive to this newly, refreshed 3/2 be ...
From $330 per night (USD)VRBO
- From $470 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 $470 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Bayfront & dog-friendly home with heated private boat dock, pool & spa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Royale View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $265 per night (USD)VRBO
- From $175 per night (USD)
Expedia
1\/1 Condo, Blocks from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Updated 1/1 Condo in a quiet community on gorgeous Anna Maria Island. We are blocks away from the beautiful white sand b ...
From $175 per night (USD)Expedia
- From $391 per night (USD)
VRBO
Island Time: 1 BR, 1.5 BA Condominium in Holmes Beach, Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Island Time 104 at Seaside Beach House is a condominium that has long been a favorite to visitors of Holmes Beach and An ...
From $391 per night (USD)VRBO
- Click For Pricing
Expedia
Luxurious Resort Sixty-Six, Studio, Not Far From Your Savory Delights
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For PricingExpedia
- Click For Pricing
VRBO
Resort Sixty-Six, Holmes Beach, Florida, Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For PricingVRBO
- Click For Pricing
Expedia
Resort Sixty-Six, Holmes Beach, Florida, 1 Bedroom Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For PricingExpedia
- From $411 per night (USD)
VRBO
WONDERFUL BEACH VIEWS AND LARGE POOL!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
4200 Gulf Drive, Holmes Beach, Anna Maria Island Gulf Sands # 203 ... Beautiful views of the gulf from this updated 2 b ...
From $411 per night (USD)VRBO
- Click For Pricing
Expedia
Amazing Resort Sixty-Six, 1 Bedroom Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For PricingExpedia
- From $234 per night (USD)
VRBO
Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Isle Haven B will let you make beautiful memories - it's the perfect beach getaway to relax and enjoy the classic Florid ...
From $234 per night (USD)VRBO
- From $213 per night (USD)
Expedia
Egret at Blue Lagoon on Anna Maria Island - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just perfect! From the tasteful beachy decor to the fully appointed kitchen you won’t find more welcoming accommodations ...
From $213 per night (USD)Expedia
- From $210 per night (USD)
VRBO
Private 3BR Heated Pool Villa - Sea Glass on Anna Maria - By Island Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
When you arrive at “SeaGlass” you are greeted with pleasant landscaping, a gorgeous brick driveway, and an adorable home ...
From $210 per night (USD)VRBO
- From $484 per night (USD)
Expedia
FALL INTO THE SEA from the porch of these one bedroom suites at Bali Hai Beachfront Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
These beachfront one bedroom suites are located directly on the Gulf of Mexico with amazing views and direct access from ...
From $484 per night (USD)Expedia
- From $295 per night (USD)
VRBO
Perfect 1-bedroom Beachfront Getaway!! See the sunsets and feel the breeze!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Highlights: -large bay of windows perfectly frame the beach from the kitchen, living, and dining areas -Screened porch - ...
From $295 per night (USD)VRBO
- From $508 per night (USD)
Expedia
Summer Wind- An island getaway in the perfect location.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience all the best elements of the perfect Island vacation in this well-appointed rental home. It is located just a ...
From $508 per night (USD)Expedia
- From $563 per night (USD)
VRBO
One block to beach! 3 bedroom home with pool and backyard oasis.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Walking on Sunshine by AMI Locals Home in Holmes Beach, Florida VRC19-000232 Your dream vacation awaits at Walking on S ...
From $563 per night (USD)VRBO
- From $396 per night (USD)
Expedia
Island Time - Home w\/Enclosed Lagoon Style Pool & Spa, Walk to Beach, Bikes!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Island Time! On Anna Maria Island (Holmes Beach, FL) Ground Level Spacious Home w/Lagoon Style Enclosed Heat ...
From $396 per night (USD)Expedia
- From $331 per night (USD)
VRBO
Island Hideaway East: 5 Minute Walk to Beach, Private Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
308B 67th St., Holmes Beach, FL 34217 What you'll love about this home: Location! 5 minute walk to the white sand beac ...
From $331 per night (USD)VRBO
- From $291 per night (USD)
Expedia
Cute 3\/2 Cottage close to Beach and centrally located.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC21-000048 Swizzle On The Sound is just a short stroll to the beautiful beaches of Anna Maria Island from your own pi ...
From $291 per night (USD)Expedia
- Click For Pricing
Expedia
Beautiful Home near Beach with Gourmet Kitchen!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Swell Life by AMI Locals Home in Holmes Beach, FL Highlights: • Private pool • Outdoor living area • Washer and dryer ...
Click For PricingExpedia
- From $224 per night (USD)
Expedia
LOCATION!! Cabana just steps from the beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Anna Maria Island the # 1 spot for a perfect getaway. Bask in the tropical paradise of AMI with white sugar ...
From $224 per night (USD)Expedia
- From $369 per night (USD)
VRBO
Dream luxury home on Anna Maria Island, heated private pool - pet friendly!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely new island 2 bedrooms, 2.5 baths luxury home with private heated pool is a dream. Fishful Thinking is positi ...
From $369 per night (USD)VRBO
- From $334 per night (USD)
Expedia
Salty Harbor AMI pool retreat near the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our charming Salty Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immedi ...
From $334 per night (USD)Expedia
- From $305 per night (USD)
VRBO
3 bedroom, on Anna Maria Island, heated private pool, PET FRIENDLY!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The family friendly Florida vacation you need is waiting at Mykonos! This Anna Maria Island beach rental has it all. Fro ...
From $305 per night (USD)VRBO
- From $1041 per night (USD)
Expedia
Conch House - 7 Homes to the Beach - Amazing Pool Area with TV
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Conch House, a Charleston inspired beach house unlike any other home and without compromise in craftsmans ...
From $1041 per night (USD)Expedia
- From $206 per night (USD)
VRBO
3 bedroom home on Anna Maria Island, great location, pet friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summer, season, or in between - this 3 bedroom, 3 bath home is your island retreat. Located in a quiet residential neigh ...
From $206 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Cozy Retro Cottage located less then 2 blocks from the Gulf Beach - Heated Pool in Private Oasis!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Flip Cottage located just 1 block from the Gulf beaches of Anna Maria Island. Flip is a ground level half dup ...
From $273 per night (USD)Expedia
- From $600 per night (USD)
VRBO
Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Imagine waking up every morning to a million dollar view and never being more than a few steps away from the pristine wh ...
From $600 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Beautiful Pool Home with Private Deck 250 Steps Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
202 56th St. #2, Holmes Beach, FL 34217 What You'll Love About This Home: Location - 250 Steps to the Beach! 1 Bedroom ...
From $249 per night (USD)Expedia
- From $262 per night (USD)
VRBO
AMI Sand Dollar: Dog Friendly, Private Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
6403 B Holmes Blvd., Holmes Beach, FL 34217 What You'll Love About This Property: Location! Two blocks to the Beach! 1 ...
From $262 per night (USD)VRBO
- From $328 per night (USD)
Expedia
Sunset Beach 102: Gulf Front, Stunning Views, On the Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2716 Gulf Dr., #102, Holmes Beach, FL 34217 What You'll Love About This Homes: Location! Beach Front with Gulf Views! ...
From $328 per night (USD)Expedia
- From $549 per night (USD)
VRBO
Barefoot Bungalow:Dog Friendly, Screened Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
213 70th St., Holmes Beach, FL 34217 What You'll Love About This Home: Location! 1.5 Blocks to the Beach! 3 Bedrooms / ...
From $549 per night (USD)VRBO
- From $362 per night (USD)
Expedia
AMI Starfish: Private Pool, Dog Friendly, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
6403 A Holmes Blvd., Holmes Beach, FL 34217 What You'll Love About This Property: Location! Two blocks to the Beach! 2 ...
From $362 per night (USD)Expedia
- Click For Pricing
Expedia
Isle Be Back 😎 | Canal front home w\/ Pool, dock, views & close to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Isle Be Back will have you wanting to come back before your stay is over! This 3 bed, 2 bath Pool home is nestled on a c ...
Click For PricingExpedia
- From $409 per night (USD)
Expedia
Rest Assured: Screened Pool,1 Block to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
210 68th St., Holmes Beach, FL 34217 What You'll Love About This Home: Location! 1 Block to the Beach 3 Bedrooms / 2. ...
From $409 per night (USD)Expedia
- From $211 per night (USD)
VRBO
Island villa with heated private pool, tranquil courtyard, easy beach access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Wave Villa West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $211 per night (USD)VRBO
- From $674 per night (USD)
Expedia
Stylish & relaxing villa with heated pool - blocks from the beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Turtle Cove East and West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $674 per night (USD)Expedia
- From $70 per night (USD)
VRBO
Peaceful condo with pool, tennis, fishing dock, & tennis - serenity awaits
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
West Bay Point 12 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $70 per night (USD)VRBO
- From $159 per night (USD)
Expedia
Newly-remodeled, dog-friendly duplex w\/ WiFi, shared heated pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Turquoise Paradise West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $159 per night (USD)Expedia
- Click For Pricing
VRBO
Charming condo with private heated pool & free WiFi - quick walk to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Turtle Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For PricingVRBO
- From $354 per night (USD)
Expedia
Beautiful lakeside home w\/ upscale amenities, heated private pool & fishing dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spectacular Saltwater Seas Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $354 per night (USD)Expedia
- From $303 per night (USD)
VRBO
Convenient cottage with pool - easy access to trolley stops & the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunfish 104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $303 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Dog-friendly seaside home - heated private pool & spa, great location near beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tropical Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $385 per night (USD)Expedia
- From $216 per night (USD)
VRBO
Dog-friendly cottage w\/ island views, shared pool & private patio - beach nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Starfish Beach Cottage #3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $216 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Welcoming condo with pool, Gulf views & great location - walk to the beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Palm Isle Village 3208 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $249 per night (USD)Expedia
- From $1355 per night (USD)
VRBO
Luxury beachside home with heated private pool - tranquil & close to everything
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Wine Down Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $1355 per night (USD)VRBO
- Click For Pricing
Expedia
Upscale tropical getaway with private pool & spa, & elevator - walk to the beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Coquina Sands Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
Click For PricingExpedia
- From $248 per night (USD)
VRBO
Waterfront condo with pool and easy access to sugar sand beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
A Gulf Front Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $248 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Brand new dog-friendly home w\/ heated private pool in prime locale
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sunset Glow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $287 per night (USD)Expedia
- From $341 per night (USD)
VRBO
Waterfront condo with furnished balcony overlooking the pristine beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gulf Shores 205 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $341 per night (USD)VRBO
- From $622 per night (USD)
Expedia
Darling beachside villa w\/ space & privacy - a cozy coastal florida experience
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Playa Casanas Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $622 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Modern home near Gulf beaches with private heated pool & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Neolinda 305 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $339 per night (USD)VRBO
- From $171 per night (USD)
Expedia
Charming condo with heated pool - near beach, wetlands, & trolley stop
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sandy Pointe Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $171 per night (USD)Expedia
- From $97 per night (USD)
VRBO
Ocean-front condo with WiFi, pool & Gulf views - steps to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Martinique 401S Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $97 per night (USD)VRBO
- From $163 per night (USD)
Expedia
Delightful condo with pool, two lanais - walk to beach, dining, shopping
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach View 5 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $163 per night (USD)Expedia