Holmes Beach Rentals
From $480 per night (USD)VRBO
Beautifully outfitted home with a heated pool and tropical backyard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Seahorse Paradise 2.5 Blocks to Beach Highlights: • Heated Pool • Tropical Backyard • Large Covered Patio • Poolside ...
From $480 per night (USD)VRBO
From $355 per night (USD)Expedia
Enjoy Endless Fun with a Private Heated Pool at Key Largo Cottage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Key Largo Cottage by Anna Maria Island Accommodations 315 62nd Street, Holmes Beach, Florida Discover the ultimate fam ...
From $355 per night (USD)Expedia
From $295 per night (USD)VRBO
Coastal Home with Heated Pool, Close to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Pineapple Palms by Anna Maria Island Accommodations Holmes Beach Vacation Home VRC17-000041 Welcome to Pineapple Palm ...
From $295 per night (USD)VRBO
From $662 per night (USD)Expedia
1.5 Blocks to Gulf Beaches, Private Heated Pool - No Bad Days
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
No Bad Days by Anna Maria Island Accommodations Home in Holmes Beach, FL VRC18-000057 Welcome to No Bad Days, an invit ...
From $662 per night (USD)Expedia
From $457 per night (USD)VRBO
Holmes Beach Gem! Pool, Grill & Game Room!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Attitude By Latitude by Anna Maria Island Accommodations Holmes Beach Vacation Home with Pool, Game Room, and Elevator ...
From $457 per night (USD)VRBO
From $270 per night (USD)Expedia
Heated Pool! Beautiful Condo, Close to Beach - Blue Lagoon 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Blue Lagoon 1 by Anna Maria Island Accommodations Holmes Beach Vacation Condo VRC16-000166 Welcome to Blue Lagoon 1, ...
From $270 per night (USD)Expedia
From $340 per night (USD)VRBO
Spacious family home with heated Pool and Spa, Close to Beach! - Shamrock Palms
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Shamrock Palms by Anna Maria Island Accommodations Holmes Beach Vacation Home VRC16-000106 Welcome to Shamrock Palms, ...
From $340 per night (USD)VRBO
From $364 per night (USD)Expedia
Close to Beach! Home with Putting Green and Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Turtle by Anna Maria Island Accommodations 5704 Holmes Boulevard, Holmes Beach, Florida 34217 VRC16-000113 Welcome ...
From $364 per night (USD)Expedia
From $272 per night (USD)VRBO
Beautiful Condo with Pool, Just Steps to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Palms 2 by Anna Maria Vacations Holmes Beach Vacation Condo VRC16-000099 Welcome to The Palms 2, a beautifully up ...
From $272 per night (USD)VRBO
From $307 per night (USD)Expedia
Island Mojo! Family-Friendly Beach Escape!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Mojo by Anna Maria Island Accommodations Holmes Beach Pool Home with Hot Tub, Near Beach and Shops VRC16-00014 ...
From $307 per night (USD)Expedia
From $407 per night (USD)VRBO
Beach Dream Cottage: Steps from the Beach with Private Pool and Spa!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beach Dream Cottage by Anna Maria Island Accommodations 5605 Carissa Street, Unit A, Holmes Beach, Florida VRC16-000637 ...
From $407 per night (USD)VRBO
From $349 per night (USD)Expedia
Completely Updated Anna Maria Island Home with Private Pool: Peach Bellini
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Peach Bellini by Anna Maria Island Accommodations Holmes Beach Vacation Rental Welcome to Peach Bellini, your perfect ...
From $349 per night (USD)Expedia
From $699 per night (USD)VRBO
6 minutes to Beach! Screened-in and Heated Pool! - Seahorse Cove
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Seahorse Cove by Anna Maria Island Accommodations Holmes Beach Beachside Duplex VRC16-000109 Welcome to Seahorse Cove ...
From $699 per night (USD)VRBO
From $389 per night (USD)Expedia
Villa with Heated Pool and Swim-up Tiki Bar! Close to Beach - La Mer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
La Mer by Anna Maria Island Accommodations 313 58 Street, Unit A, Holmes Beach, Florida 34217 VRC18-000126 Welcome to ...
From $389 per night (USD)Expedia
From $585 per night (USD)VRBO
Perfect Family Vacation Home with Pool, Lounge, and Ping Pong!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Cottage by Anna Maria Island Accommodations Holmes Beach Vacation Home VRC16-000159 Welcome to Coconut Cottag ...
From $585 per night (USD)VRBO
From $302 per night (USD)Expedia
Home with Private Pool, Two Blocks from the Beach! - Queen Palms
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Queen Palm by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC19-000042 Welcome to Queen Palm! Th ...
From $302 per night (USD)Expedia
From $708 per night (USD)VRBO
Canal Front Family Home with Private Dock and Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Jackie’s Cottage by Anna Maria Island Accommodations Holmes Beach Canal Front Retreat with Dock VRC18-000190 Welcome ...
From $708 per night (USD)VRBO
From $509 per night (USD)Expedia
Gorgeous Home with a Pool, Outdoor Lounge, and Elevator! Close to the Beach and
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ohana by Anna Maria Island Accommodations 4807 2nd Avenue, Holmes Beach, Florida 34217 Experience the perfect family v ...
From $509 per night (USD)Expedia
From $710 per night (USD)VRBO
Stunning Home with Pool, Tiki Bar, and Game Room! 2 Minute Walk to Beach - Marga
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Margarita-Ville by Anna Maria Island Accommodations 121 46th Street, Holmes Beach, Florida 34217 VRC16-000136 Experien ...
From $710 per night (USD)VRBO
From $181 per night (USD)Expedia
Beach Home with Pool Access and Private Patio with BBQ Grill! - Little Dream
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Little Dream by Anna Maria Accommodations Holmes Beach Cozy Beach Retreat VRC16-000139 Welcome to Little Dream! A cha ...
From $181 per night (USD)Expedia
From $503 per night (USD)VRBO
Beautiful home with pool, elevator, and ping pong table
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beach Retreat by Anna Maria Island Accommodations Home in Holmes Beach, FL 1 Block to Beach Highlights • 2-minute wa ...
From $503 per night (USD)VRBO
From $840 per night (USD)Expedia
Near the Beach with Balconies and Tiki Bar
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Two Pina Coladas by Anna Maria Island Accommodations Home in Holmes Beach, FL 1 Block to Beach Highlights: • Heated P ...
From $840 per night (USD)Expedia
From $549 per night (USD)VRBO
Gulf front condo with amazing views and beach access! - Palm Gables 112
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Gables 112 by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC18-000128 Experience the epit ...
From $549 per night (USD)VRBO
From $1005 per night (USD)Expedia
Poseidon’s Palace! Family Fun & Gulf Views!
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 16
Poseidon’s Palace by Anna Maria Island Accommodations Luxury 8-Bedroom Retreat with Rooftop Deck, Pool, and Spa VRC16 ...
From $1005 per night (USD)Expedia
From $781 per night (USD)VRBO
Sea Oats: Anna Maria Island Family Retreat with Pool Just Steps from the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Sea Oats by Anna Maria Island Accommodations Home in Holmes Beach, Florida VRC16-000115 Welcome to Sea Oats, your ul ...
From $781 per night (USD)VRBO
From $377 per night (USD)Expedia
Vibrant Island Retreat with Pool, Tiki Table and Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ainsley Beach House by Anna Maria Island Accommodations Vibrant Island Retreat with Pool, Tiki Table and Walk to Beach ...
From $377 per night (USD)Expedia
From $383 per night (USD)VRBO
Coral Palms: 3BR Updated Rental with Private Pool near Gulf of Mexico Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coral Palms by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC16-000157 Welcome to Coral Palms, a ...
From $383 per night (USD)VRBO
From $241 per night (USD)Expedia
Quiet Villa, Steps to Beach! Close To Trolley Stop and Shopping! - Sea Glass Vil
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sea Glass Villa by Anna Maria Island Accommodations Holmes Beach Oceanfront Retreat with Pool and Tiki Hut VRC20-00018 ...
From $241 per night (USD)Expedia
From $357 per night (USD)VRBO
Updated Home, 5 Houses from the Beach! Private Pool and Game Room! - Ocean's 77
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ocean's 77 by Anna Maria Island Accommodations Holmes Beach Beachside Retreat with Pool & Game Room 205 77th Street, U ...
From $357 per night (USD)VRBO
From $531 per night (USD)Expedia
Beautiful Villa near the Beach with Pool! - Mermaid's Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mermaid's Hideaway by Anna Maria Island Accommodations Holmes Beach Walkable Beachfront Home with Pool VRC16-000135 E ...
From $531 per night (USD)Expedia
From $333 per night (USD)VRBO
Family-Friendly Home, Steps from the Beach with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Addison’s Beach House by Anna Maria Island Accommodations Holmes Beach Family Beach Retreat with Pool VRC16-000188 We ...
From $333 per night (USD)VRBO
From $359 per night (USD)Expedia
Gorgeous Villa, with Private Heated Pool and Tiki Bar
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Serendipity by Anna Maria Island Accommodations Holmes Beach Private Villa with Pool VRC16-000107 Welcome to Serendip ...
From $359 per night (USD)Expedia
From $261 per night (USD)VRBO
Perfect family vacation home with private pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Aggies Treasure by Anna Maria Island Accommodations 203 70th St, Unit A (West Unit) Holmes Beach, FL 34217 One Block to ...
From $261 per night (USD)VRBO
From $399 per night (USD)Expedia
Beachfront Balcony, Stylish Gulf-View Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Gables 110 by Anna Maria Vacations Holmes Beach Beachfront Condo 110 36th St, Holmes Beach, FL 34217 Welcome to ...
From $399 per night (USD)Expedia
From $193 per night (USD)VRBO
Canal front Cottage Near the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stars on the Water by AMI Locals Canal Front Vacation Home with Dock near Manatee Beach VRC21-000115 Perfect for beac ...
From $193 per night (USD)VRBO
From $456 per night (USD)Expedia
Happy Island Cottage with Heated Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A 2000 sq/ft, 3 bedroom modern beach house with heated* and very private pool. A perfect location just steps from the be ...
From $456 per night (USD)Expedia
From $407 per night (USD)VRBO
Walk to Shore: Holmes Beach Home w/ Pool & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pet Friendly w/ Fee + Owner Approval | Beach Gear w/ Wagon Nestled in a quiet cul-de-sac on the west side of Anna Marie ...
From $407 per night (USD)VRBO
From $371 per night (USD)VRBO
Private Pool - Manna-Tee Beach House by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot fo ...
From $371 per night (USD)VRBO
From $301 per night (USD)VRBO
Beachfront Condominium on the white sandy beach of Anna Maria Island.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Sun Plaza West Beachfront Condominiums. This complex is ON the beach. It doesn’t get better than that. This b ...
From $301 per night (USD)VRBO
From $429 per night (USD)Expedia
GULF FRONT Beautiful Condo, Heated Pool, FREE WiFi & Trolley, Great Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
**ASK ABOUT LAST-MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two-bedroom ...
From $429 per night (USD)Expedia
From $436 per night (USD)VRBO
Buddy’s Beach House Private Heated Pool and Spa- Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Buddy's Beach House, a completely remodeled, beachy chic getaway just 2 blocks to the beach. Stroll to the be ...
From $436 per night (USD)VRBO
From $516 per night (USD)Expedia
Dog Friendly Home with Private Pool and Spa! Close to Beach - Sunset and Sands
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sunset and Sands by Anna Maria Island Accommodations 200 81st Street, Holmes Beach, 34217 VRC17-000117 Welcome to Suns ...
From $516 per night (USD)Expedia
From $455 per night (USD)VRBO
Fun family vacation home, just one block to the AMI beach. You'll love the pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Pineapple by AMI Locals Home in Holmes Beach, Florida CAA20-000023 Paradise awaits at Blue Pineapple, a gorgeo ...
From $455 per night (USD)VRBO
From $743 per night (USD)Expedia
PRIVATE HOUSE and Pool on AMI. Close to beach, shopping, restaurants, marina.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SALTY DOGS ON ANNA MARIA ISLAND IS WAITING FOR YOU! SALTY DOGS IS A SINGLE-FAMILY BEACH HOUSE. You get the entire h ...
From $743 per night (USD)Expedia
From $280 per night (USD)VRBO
Steps to Beach - Tropical Sunset 1 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for the perfect beach destination? Well, it doesn't get better than this! This 2 bedroom/2 bath condo, recently ...
From $280 per night (USD)VRBO
From $350 per night (USD)Expedia
Coastal living at its finest! Inviting two bedroomwith Pool & Jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your tranquil haven nestled in the heart of Anna Maria Island! This enchanting 2-bedroom, 2-bathroom residenc ...
From $350 per night (USD)Expedia
From $340 per night (USD)VRBO
Esxape to Paradise! Beachside retreat with shared pool spa. 5 min walk to beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to paradise. Serene 2-Bedroom Retreat with Pool and Jacuzzi Experience the epitome of modern comfort at this go ...
From $340 per night (USD)VRBO
From $481 per night (USD)Expedia
Private paradise w/ all the beach supplies & toys!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Laguna is a privately owned home with private amenities and entry via smart locks. The home is surrounded by lush ...
From $481 per night (USD)Expedia
From $338 per night (USD)VRBO
Coconuts 116 - Anna Maria Island - Condo -1 Bedroom/ 1 Bath- maximum...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Coconuts 116 - Anna Maria Island - 1 Bedroom/ 1 Bath - maximum occupancy of 6 people. VRC21-000194 Distance to the ...
From $338 per night (USD)VRBO
From $552 per night (USD)Expedia
Sunsets on Carissa - Coastal Retreat w/ Heated Pool, Game Room & Steps from Gulf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sunsets on Carissa! On Anna Maria Island (Holmes Beach, FL) Experience Sunsets On Carissa – A Modern Coastal ...
From $552 per night (USD)Expedia
From $471 per night (USD)VRBO
Fins Up – AMI Cozy Island Retreat w/ Private Pool & 4-Min Walk To Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Fins Up! On Anna Maria Island (Holmes Beach, FL) Discover Fins Up, An AMI Island Getaway Where A Private Poo ...
From $471 per night (USD)VRBO
From $204 per night (USD)Expedia
Spinnakers Cottages - Cabin 1 - Dog Friendly - 250 Steps to Beach, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cabin 1 Spinnakers Cottages by Anna Maria Life Vacation Rentals 204 56th St. #1, Holmes Beach, FL 34217 What You'll Lov ...
From $204 per night (USD)Expedia
From $277 per night (USD)VRBO
Island Vibe 5: Close to Beach with Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Island Vibe 5! This is a newly renovated 2-bedroom, 2-bathroom home with private, heated and cooled pool, tro ...
From $277 per night (USD)VRBO
From $440 per night (USD)Expedia
Anna Maria Island!1 Block to the Beach. Private Home with Heated Pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the ultimate luxury of this beautiful private home just minutes from the white private sandy beaches of Anna ...
From $440 per night (USD)Expedia
From $315 per night (USD)VRBO
Perfect Vacation Home with Private Pool! Close to the Beach! - Gulf Breeze
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gulf Breeze by AMI Locals Holmes Beach Beach Retreat with Private Pool VRC21-000001 Welcome to Gulf Breeze, a charmin ...
From $315 per night (USD)VRBO
From $318 per night (USD)Expedia
Charming Island Pool Home | Walk to Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Breeze by AMI Locals Island Hideaway with Private Pool Near Holmes Beach 306 65th St, Unit B | Holmes Beach, Flor ...
From $318 per night (USD)Expedia
From $291 per night (USD)VRBO
Cozy Home with Private Pool, Close to the Beach! Don't Miss Out!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Escape by AMI Locals Holmes Beach Private Home with Pool and Walkable Beach Access VRC21-000012 Welcome to Isl ...
From $291 per night (USD)VRBO
From $548 per night (USD)Expedia
Golf cart Inc + 4bd/2bth + private pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Recent Review: "This is an incredible place to stay. The location is awesome, the communication is phenomenal and the ho ...
From $548 per night (USD)Expedia
From $218 per night (USD)VRBO
Gulf Beach Apartment - with Pool & Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pristine,spacious1 bedroom apartment sleeps 4, only steps to the beautiful white sandy beach of Anna Marie Island. Fresh ...
From $218 per night (USD)VRBO
From $280 per night (USD)VRBO
Your island destination steps from the beach!<br>
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tortuga tides is your extended vacation oasis steps from the white sands of Anna Maria Island beaches. The master bedroo ...
From $280 per night (USD)VRBO
From $253 per night (USD)VRBO
Newly renovated Cozy Beach Cottage B 1/2 of a duplex, 3min walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly remodeled 2beds/1bath 1/2 of the duplex, just short walk (3-5min)to the white sandy beaches of Anna ...
From $253 per night (USD)VRBO
From $254 per night (USD)Expedia
Newly renovated Cozy Beach Cottage A1/2 of a duplex, 3min walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly remodeled 2beds/1bath 1/2 of the duplex, UNIT A - just short walk (3-5min)to the white sandy beach ...
From $254 per night (USD)Expedia
From $881 per night (USD)VRBO
Surfside AMI; backyard oasis steps to beach, heated pool, putting green,+gear!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Recently renovated in 2025, new kitchen, flooring and updated furnishings! Private beach getaway with a backyard oasis i ...
From $881 per night (USD)VRBO
From $491 per night (USD)Expedia
Villa Verde-4 bedroom with private pool with restaurants and boutiques nearby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
311 61st Street is a lovely elevated 4 bedroom and 3.5 bathroom tucked away in the heart of Holmes Beach just a short tw ...
From $491 per night (USD)Expedia
From $522 per night (USD)VRBO
Golf Cart, Island Haven by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL RESERVATIONS STAYING DURING 2025! All Drivers must be over the age of 21. Drivers mus ...
From $522 per night (USD)VRBO
From $378 per night (USD)VRBO
Bay Palms,3BR 2B , Private Pool with Spa--Entire Home recently renovated.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our home has 3 bedrooms, master with queen bed and ensuite bathroom, 2nd bedroom has a queen bed, 3rd bedroom has two tw ...
From $378 per night (USD)VRBO
From $387 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come soak in the picturesque gulf views of Anna Maria Island at this newly renovated, contemporary beach condo! This 1 b ...
From $387 per night (USD)VRBO
From $232 per night (USD)Expedia
Perfect Family Vacation home just off the beach! Private Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Hideaway by AMI Locals Home in Holmes Beach, FL Features: • Private heated pool • Ground-level home, very access ...
From $232 per night (USD)Expedia
From $390 per night (USD)VRBO
Sun Plaza West Unit 204, gulf front complex on AMI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Important Update, Pool will be closed from July to Mid- September 2025* Come experience Unit 204 at Sun Plaza Wes ...
From $390 per night (USD)VRBO
From $357 per night (USD)Expedia
Recently Renovated Luxury Ground Floor Island Home Close to Beach!o Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Limbo Cottage - the west side of 'Gumbo Limbo' duplex. Located just 7 houses from the Gulf beaches of Anna Ma ...
From $357 per night (USD)Expedia
From $323 per night (USD)VRBO
BEAUTIFUL 3/2 TOWNHOME w/ HEATED PRIVATE POOL. STEPS FROM THE GULF BEACHES!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Welcome to your Anna Maria Island vacation! You will enjoy your time at thi ...
From $323 per night (USD)VRBO
From $581 per night (USD)VRBO
CONTEMPORARY BEACH CHIC HOME WITH OCEAN VIEWS, STEPS TO THE BEACH/HEATED POOL\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
THE POOL IS PRIVATE AND ONLY FOR THE USE OF THE GUESTS IN THIS HOME WHICH IS SEABREEZE SANDS. IT IS NOT SHARED WITH ANY ...
From $581 per night (USD)VRBO
Click For PricingVRBO
Lovely corner home near the beach with private pool/spa, WiFi & central AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Mermaid Sunset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For PricingVRBO
From $351 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
With a bright green-colored exterior and vibrant greenery surrounding the property, LaBella Casa is hard to miss! And, y ...
From $351 per night (USD)Expedia
From $313 per night (USD)VRBO
Old Florida living only 200 steps to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Paradise found! With only 200 steps to the beach, this lovely beach house offers a great value for you vacation. A sho ...
From $313 per night (USD)VRBO
From $317 per night (USD)VRBO
Pool/Spa - Bahama Mama by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is it - Paradise! This fabulous Key West style elevated 3 bedroom/2 bath single family home has so many wonderful f ...
From $317 per night (USD)VRBO
From $435 per night (USD)VRBO
Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
"Calypso" is a Newly remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall, ...
From $435 per night (USD)VRBO
From $311 per night (USD)VRBO
Island Vibe 6: Close to Beach with Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Island Vibe 6! This is a newly renovated 2-bedroom, 2-bathroom home with private, heated and cooled pool, tro ...
From $311 per night (USD)VRBO
From $318 per night (USD)VRBO
Palms Beach West - Holmes Beach Vacation Villa - 3 Bedroom with Private Pool - B
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make memories that last a lifetime when you stay at gorgeous Anna Maria Island vacation rental home “Palms Beach West”. ...
From $318 per night (USD)VRBO
From $143 per night (USD)VRBO
Sandy Pointe II Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This is a light and bright 2 bedroom/2 bath Condo that backs up to the lovely and serene mangroves (nature preserve). T ...
From $143 per night (USD)VRBO
From $187 per night (USD)VRBO
STEPS TO GULF BEACH!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Authentic ground floor Bungalow with private parking and seashell courtyard just steps away from the Gulf Beaches. Cozy ...
From $187 per night (USD)VRBO
From $519 per night (USD)VRBO
Direct Beachfront 2 BD Condo On Florida’s Beautiful Gulf Coast!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Florida Vacation Dream Spot - easy and fun! This 2 Bedroom, 2 Bath condo is direct beachfront with wide open views up a ...
From $519 per night (USD)VRBO
From $378 per night (USD)VRBO
Sandcastle by the Sea managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
213 76th St. Bradenton Beach, Fl 34217 VRC21-000119 “You are vacationing in a residential area. Please be a good neighb ...
From $378 per night (USD)VRBO
From $249 per night (USD)Expedia
Close to the beach on Anna Maria Island, 2 bedroom, condo & community pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We welcome you to our beautifully remodeled Anna Maria Island vacation rental condo! Summer of 2020 brought many updates ...
From $249 per night (USD)Expedia
From $214 per night (USD)VRBO
Pet-Friendly - Rum Dog by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfect for a family vacation or a couple's retreat, this newly listed and newly updated, furnished 2 bedroom/2 bath dup ...
From $214 per night (USD)VRBO
From $348 per night (USD)Expedia
One Day More: Spectacular Oasis Backyard with Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
403 72nd St., Holmes Beach, FL 34217 What You'll Love About this Home: Location! 4 Blocks to the Beach! Centrally Locat ...
From $348 per night (USD)Expedia
From $292 per night (USD)VRBO
Beautiful AMI Beach House with Heated Pool and Fenced Backyard!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sol y Mar by AMI Locals Holmes Beach Modern Beach House with Pool VRC21-000118 Welcome to Sol y Mar, a bright and new ...
From $292 per night (USD)VRBO
From $219 per night (USD)VRBO
END OF SUMMER SPECIAL- Private patio-Central location & trolley-3min to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This is a fabulously styled cottage is set back 30 yards from the Gulf ocean (one house off the beach as the crow flies) ...
From $219 per night (USD)VRBO
From $212 per night (USD)VRBO
END OF SUMMER RATES! Cozy cottage central location-Private patio-3 min to beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover this boutique-styled cottage and the white sandy beaches that make Anna Maria Island so famous. The Cottage is ...
From $212 per night (USD)VRBO
From $587 per night (USD)Expedia
One Bedroom Condo at Beachfront Resort!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconuts Courtyard! This amazing condo is located within the iconic Coconuts Beach Resort located directly on ...
From $587 per night (USD)Expedia
From $620 per night (USD)VRBO
Unwind Sunshine - heated pool, steps to the local's favorite beach, free bikes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
***WEEKLY RENTAL**** This Luxury beach chic cottage home has it all....location, fully stocked luxury kitchen, and beac ...
From $620 per night (USD)VRBO
From $406 per night (USD)Expedia
GULF FRONT Beautiful Condo w/Heated Pool, FREE WiFi & Trolley, Great Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom ...
From $406 per night (USD)Expedia
From $466 per night (USD)VRBO
Large Private Pool Home with Spa - 150 yards to the Beach - By Island Real Estat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
“Catchin’ Rays” is an excellent choice for your next Anna Maria Island vacation! This centrally located home offers ever ...
From $466 per night (USD)VRBO
From $274 per night (USD)Expedia
Sam's Cove! Second Floor Condo Overlooking Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
IMPORTANT: Per homeowner's association, a minimum monthly stay is required, as well as an application. Please allow at l ...
From $274 per night (USD)Expedia
From $564 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Photos updated March 2025 Welcome to the graceful beauty of Stillpoint, an island retreat for family and friends just s ...
From $564 per night (USD)VRBO
From $369 per night (USD)Expedia
New To The Rental Market Just Steps To The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
VRC22-000010 and VRC22-000022 Made In the Shade is thoroughly cleaned and sanitized prior to your arrival. We pay speci ...
From $369 per night (USD)Expedia
From $203 per night (USD)VRBO
Stylish, Sunny, Steps to the Sand
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC22-000010 Tucked into a quiet street and with your beach access across the street, Made in the Shade A is a one-bedr ...
From $203 per night (USD)VRBO
From $197 per night (USD)Expedia
Coastal Calm Steps from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC22-000022 Hidden just feet from the Gulf of Mexico’s powder-soft sands, Made in the Shade B offers everything you ne ...
From $197 per night (USD)Expedia
From $475 per night (USD)VRBO
Cozy corner beach house with pool- 1 block from beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Casa de Palmas is a charming 3 bedroom and 3 bath private beach house, located one block from the turquoise waters of th ...
From $475 per night (USD)VRBO
From $457 per night (USD)Expedia
Blue Palm Paradise: Dog friendly, Pool, 3 Minute Walk to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Palm Paradise by Anna Maria Life Vacation Rentals 205 65th St, Holmes Beach, FL 34217 What You'll Love About This ...
From $457 per night (USD)Expedia