Holmes Beach Rentals
- From $245 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 $245 per night (USD)VRBO
- From $335 per night (USD)
Expedia
Beach Bliss managed by Beach Retreats
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
320 64th Street - Holmes Beach - FL - 34217 VRC17-000113 Incredible 3 Bed 3 Bath bungalow, Minutes From The Beach With ...
From $335 per night (USD)Expedia
- From $255 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 $255 per night (USD)VRBO
- From $120 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 $120 per night (USD)Expedia
- From $488 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 $488 per night (USD)VRBO
- From $153 per night (USD)
Expedia
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 $153 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $151 per night (USD)
Expedia
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 $151 per night (USD)Expedia
- From $483 per night (USD)
VRBO
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 $483 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 $277 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 $277 per night (USD)VRBO
- From $277 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 $277 per night (USD)Expedia
- From $159 per night (USD)
VRBO
Bayside Holmes Beach 3 Bed\/2 Bath Ground Floor Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy this spacious updated condo in a beautifully landscaped, quiet bayside complex with heated pool and private pickle ...
From $159 per night (USD)VRBO
- From $132 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 $132 per night (USD)VRBO
- From $878 per night (USD)
VRBO
Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Copy this link to your browser to see 3D view of Emerald Seas floor plan: https://www.zillow.com/view-3d-home/d7fdf4d1- ...
From $878 per night (USD)VRBO
- From $159 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 $159 per night (USD)Expedia
- From $199 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 $199 per night (USD)VRBO
- From $482 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 $482 per night (USD)Expedia
- From $440 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 $440 per night (USD)VRBO
- From $499 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 $499 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Oleander Villa by Beach Boutique Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Oleander Villa is a true ...
From $179 per night (USD)VRBO
- From $861 per night (USD)
Expedia
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 $861 per night (USD)Expedia
- From $199 per night (USD)
VRBO
Orchid Villa by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Orchid Villa is a true i ...
From $199 per night (USD)VRBO
- From $231 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 $231 per night (USD)Expedia
- From $153 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 $153 per night (USD)VRBO
- From $498 per night (USD)
Expedia
Mermaid's Crossing managed by Beach Retreats
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
210 65th Street Holmes Beach, FL 34216 VRC17-000007 Book with confidence: You may cancel your reservation up to 60 days ...
From $498 per night (USD)Expedia
- From $173 per night (USD)
VRBO
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 $173 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 $230 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 $230 per night (USD)VRBO
- From $274 per night (USD)
Expedia
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 $274 per night (USD)Expedia
- From $206 per night (USD)
VRBO
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 $206 per night (USD)VRBO
- From $317 per night (USD)
Expedia
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 $317 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Windshore A! - 2 Minute Walk to Beach, Private Heated Pool, WIFI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Built new in 2011, Windshore A leaves no wishes open when it comes to your vacation on Anna Maria Island. Within walking ...
From $400 per night (USD)VRBO
- From $292 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 $292 per night (USD)Expedia
- From $520 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 $520 per night (USD)VRBO
- From $198 per night (USD)
Expedia
Frangipani Villa by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Frangipani Villa is a tr ...
From $198 per night (USD)Expedia
- From $199 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 $199 per night (USD)VRBO
- From $219 per night (USD)
Expedia
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 $219 per night (USD)Expedia
- From $152 per night (USD)
VRBO
Anthony Beach Cottages - Bare Feet Retreat - 2 bedroom pool cottage - Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This Florida home backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably ...
From $152 per night (USD)VRBO
- From $186 per night (USD)
Expedia
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 $186 per night (USD)Expedia
- From $372 per night (USD)
VRBO
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 $372 per night (USD)VRBO
- From $109 per night (USD)
VRBO
Great Island Getaway!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful 2 BR/2 BA condo is all about charm and comfort. You will have no problem leaving your cares behind and e ...
From $109 per night (USD)VRBO
- From $166 per night (USD)
VRBO
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. You will be blocks away from the beautiful white ...
From $166 per night (USD)VRBO
- From $311 per night (USD)
Expedia
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 $311 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $302 per night (USD)
Expedia
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 $302 per night (USD)Expedia
- 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
- Click For Pricing
VRBO
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 PricingVRBO
- From $263 per night (USD)
VRBO
Closer to the beach does not work: comfortable apartment at ground level on the beach.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ATTENTION: We rent with 1 week minimum: Saturday to Saturday Old Florida Feeling: bungalow right on the beach on level - ...
From $263 per night (USD)VRBO
- From $180 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 $180 per night (USD)VRBO
- From $473 per night (USD)
Expedia
⚓Private pool home 5 min> walk to beach!⚓🐕🏖🌅
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Sweet Home Anna Maria! ⚓Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! ⚓Private ...
From $473 per night (USD)Expedia
- From $122 per night (USD)
VRBO
Carissa Beach House: Affordable & cute apartment on Anna Maria Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Carissa Beach House is a vacation rental on Anna Maria Island (between Tampa & Sarasota), situated about 350 steps from ...
From $122 per night (USD)VRBO
- From $217 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 $217 per night (USD)Expedia
- From $369 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 $369 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $345 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 $345 per night (USD)VRBO
- From $711 per night (USD)
VRBO
TRUE BEACHFRONT HOME DIRECTLY ON SUGAR WHITE SANDS WITH HEATED POOL - IDYLLIC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We are excited to announce some upgrades to this very popular vacation home. The house has been painted throughout in De ...
From $711 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Dragonfly Breeze - Private Home w\/ Heated Pool, Fee Wifi, Steps to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Dragonfly Breeze, a 3 bedroom and 2 bathroom elevated private pool home located in Holmes Beach, just a short ...
From $250 per night (USD)VRBO
- From $295 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 $295 per night (USD)Expedia
- From $398 per night (USD)
VRBO
Island Time - Home w\/Enclosed Lagoon Style Pool & Spa, Walk to Beach!
- 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 $398 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Luxury Beachfront Condo with Elevator
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Gulfsands is one of the premier low density complexes and one of the most highly sought after condo complexes on Anna Ma ...
From $250 per night (USD)VRBO
- From $405 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 $405 per night (USD)VRBO
- From $225 per night (USD)
Expedia
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 $225 per night (USD)Expedia
- From $263 per night (USD)
VRBO
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 $263 per night (USD)VRBO
- 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 $196 per night (USD)
VRBO
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 $196 per night (USD)VRBO
- From $304 per night (USD)
Expedia
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 $304 per night (USD)Expedia
- From $497 per night (USD)
VRBO
Villa by the Sea managed by Beach Retreats
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Villa by the Sea is an immaculate beach retreat in the exclusive beachfront La Plage condominium complex which offers a ...
From $497 per night (USD)VRBO
- From $1250 per night (USD)
Expedia
AMI’s Largest Rental, 4 kitchens, Spa, Heated Pool, Tiki Bar, Rooftop Deck.
- Bedrooms:
- 9
- Bathrooms:
- 10
- Sleeps:
- 28
This large fully updated 6000 square foot home is a unique property to the vacation rental market with its 8 person spa, ...
From $1250 per night (USD)Expedia
- From $296 per night (USD)
VRBO
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 $296 per night (USD)VRBO
- From $495 per night (USD)
VRBO
Large Beach Home 5 houses to beach, Heated Pool, Game Room, Sun deck, Tiki bar
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This spacious property has a Tiki Bar by the heated pool, large kitchen with 4 bedrooms and 4 bathrooms, a large second ...
From $495 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Enjoy the Island Life on Anna Maria Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The location is very quiet and private. It's a short walk to Holmes Beach, Duffy s Tavern, Hurricane Hanks, The Feast, ...
From $150 per night (USD)VRBO
- From $280 per night (USD)
Expedia
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 $280 per night (USD)Expedia
- From $926 per night (USD)
VRBO
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 $926 per night (USD)VRBO
- From $179 per night (USD)
Expedia
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 $179 per night (USD)Expedia
- From $243 per night (USD)
VRBO
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 $243 per night (USD)VRBO
- From $400 per night (USD)
Expedia
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 $400 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Beautiful Pool Home with Private Deck 250 Steps Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Crow's Nest Spinnakers Cottages by Anna Maria Life Vacation Rentals 202 56th St. #2, Holmes Beach, FL 34217 What You'll ...
From $175 per night (USD)VRBO
- From $438 per night (USD)
Expedia
Starfish Isle managed by Beach Retreats
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
VRC 21-000046 5803 Holmes Blvd Holmes Beach, FL 34217 At 4 bedrooms and 3 full bathrooms, this is a great option for one ...
From $438 per night (USD)Expedia
- From $498 per night (USD)
VRBO
Conch Out Beach House managed by Beach Retreats
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
303 68th St, Holmes Beach 34217 VRC - 19-000273 You may cancel your reservation up to 60 days before check-in for a ful ...
From $498 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Starfish Cove managed by Beach Retreats
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
302 60th Street Holmes Beach, FL 34217 VRC19-000274 At 3 bedrooms and 2 full bathrooms, this is a beautiful choice for y ...
From $339 per night (USD)Expedia
- From $198 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
AMI Sand Dollar by Anna Maria Life Vacation Rentals 6403 B Holmes Blvd, Holmes Beach, FL 34217 What You'll Love About T ...
From $198 per night (USD)VRBO
- From $207 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 $207 per night (USD)Expedia
- From $325 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 $325 per night (USD)VRBO
- From $175 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
AMI Starfish by Anna Maria Life Vacation Rentals 6403 A Holmes Blvd., Holmes Beach, FL 34217 What You'll Love About Thi ...
From $175 per night (USD)Expedia
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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 $255 per night (USD)
Expedia
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 $255 per night (USD)Expedia
- From $513 per night (USD)
VRBO
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 $513 per night (USD)VRBO
- From $72 per night (USD)
Expedia
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 $72 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $256 per night (USD)
VRBO
Beautiful condo with pool, easy beach access & balcony - walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Latitude Adjustment Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $256 per night (USD)VRBO
- From $182 per night (USD)
Expedia
Stylish duplex with pool & easy beach access plus free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Turtle Cove East Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $182 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $330 per night (USD)
Expedia
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 $330 per night (USD)Expedia
- From $354 per night (USD)
VRBO
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 $354 per night (USD)VRBO
- From $270 per night (USD)
Expedia
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 $270 per night (USD)Expedia
- From $363 per night (USD)
VRBO
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 $363 per night (USD)VRBO
- From $1516 per night (USD)
Expedia
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 $1516 per night (USD)Expedia