Holmes Beach Rentals
From $312 per night (USD)VRBO
AMI Duplex with Private Pool, 5 Minutes to the Beach! - Hawaiian Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Hawaiian Hideaway by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000298 Welcome to Hawaiian Hideawa ...
From $312 per night (USD)VRBO
From $446 per night (USD)Expedia
Home with Private Pool, 8 minute walk to Beach! - Villa Portofino
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Villa Portofino by Anna Maria Vacations VRC18-000050 Experience the perfect family vacation at Villa Portofino, a char ...
From $446 per night (USD)Expedia
From $650 per night (USD)VRBO
Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Home in Holmes Beach, Florida VRC17-000129 Experience the ultimate Gulf Coast escape at Caribbean Dream, a luxurious ...
From $650 per night (USD)VRBO
From $608 per night (USD)Expedia
Beach Home with Pool, Tiki Bar, and Game Room!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Mango Breeze by Anna Maria Vacations Home in Holmes Beach, Florida VRC17-000130 Welcome to Mango Breeze, a charming ...
From $608 per night (USD)Expedia
From $898 per night (USD)VRBO
Pool, Spa, Games, and Tiki Bar! 1 Block from Beach! - View of the Gulf
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
View of the Gulf by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000749 Experience coastal luxury at V ...
From $898 per night (USD)VRBO
From $396 per night (USD)Expedia
Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Calypso Cottage by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000622 Your island vacation starts at Cal ...
From $396 per night (USD)Expedia
From $890 per night (USD)VRBO
Easy Walk to the Beach, Private Pool, Game Room, Rooftop Deck! - Tiki Beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Tiki Beach by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000263 Welcome to Tiki Beach, a stunning three ...
From $890 per night (USD)VRBO
From $571 per night (USD)Expedia
Elevated Beach Home with Gulf Views! Next to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Starfish by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000247 Experience the best of Anna Maria Isla ...
From $571 per night (USD)Expedia
From $278 per night (USD)VRBO
Pet Friendly Private Duplex. Fenced Yard with Private Pool Short Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hawaiian Tide by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC17-000059 Escape to Hawaiian Tide, a bright ...
From $278 per night (USD)VRBO
From $327 per night (USD)Expedia
Large Private Beach Home! Heated Pool, Elevator, Balcony, and Near the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Seabreeze Cottage by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000366 Enjoy the perfect blend of islan ...
From $327 per night (USD)Expedia
From $341 per night (USD)VRBO
Home with Pool, Outdoor Bar, Ping Pong, Close to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Dolphin House by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000338 Experience the tropical charm and l ...
From $341 per night (USD)VRBO
From $360 per night (USD)Expedia
Away To Play! Pool, Balconies and Steps to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Away To Play by Anna Maria Vacations Home in Holmes Beach, Florida VRC20-000047 Welcome to Away To Play, a charming ...
From $360 per night (USD)Expedia
From $405 per night (USD)VRBO
Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Pineapple Key by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000364 Welcome to Pineapple Key, a charmi ...
From $405 per night (USD)VRBO
From $493 per night (USD)Expedia
10 Minute Walk to the Beach! Private Heated Pool, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ocean Breeze by Anna Maria Vacations Duplex in Holmes Beach, Florida VPR16-000337 Discover Ocean Breeze, a perfect ...
From $493 per night (USD)Expedia
From $391 per night (USD)VRBO
Beautiful Home Private Pool, Game Room, and Close to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Key Lime Beach House by AMI Locals Home in Holmes Beach, Florida VRC000324 Welcome to Key Lime Beach House, a stun ...
From $391 per night (USD)VRBO
From $733 per night (USD)Expedia
Private Pool, Game Room, and 2 minutes to the beach - Gulfside Oasis
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Gulfside Oasis by Anna Maria Vacations Home in Holmes Beach, Florida Escape to Gulfside Oasis, a stunning multi-level ...
From $733 per night (USD)Expedia
From $533 per night (USD)VRBO
Hidden Cove #4! Beachfront Townhouse with Gulf Views and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Hidden Cove #4 by Anna Maria Vacations Condo in Holmes Beach, Florida VRC16-000044 Welcome to Hidden Cove #4, a beauti ...
From $533 per night (USD)VRBO
From $424 per night (USD)Expedia
Private Home with Pool, Near the Beach - Sand Dollar
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sand Dollar by Anna Maria Vacations Home in Holmes Beach, Florida VR16-000501 Escape to Sand Dollar, a blissful i ...
From $424 per night (USD)Expedia
From $235 per night (USD)VRBO
Beach Front Duplex! With Direct Beach Access and Scenic Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whispering Waves East by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000273 Welcome to Whispering Wav ...
From $235 per night (USD)VRBO
From $270 per night (USD)Expedia
Oceanfront Duplex with Scenic Beach Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whispering Waves West by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000272 Welcome to Whispering Wave ...
From $270 per night (USD)Expedia
From $270 per night (USD)VRBO
Beachfront Condo, Pool, Tennis Court, and Private Balcony - Sun Plaza West 110
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sun Plaza West Unit 110 by Anna Maria Vacations Holmes Beach Beachside Condo VRC17-000125 Experience Island life a ...
From $270 per night (USD)VRBO
From $298 per night (USD)Expedia
Vacation Escape with Private Pool, Grill and Beach Gear! Near Beach and Dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sugar Beach by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000340 Make your vacation dreams come tru ...
From $298 per night (USD)Expedia
From $507 per night (USD)VRBO
Private Home 5 min to Beach, Heated Pool, Fully Equipped Kitchen! - Stay Calm
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay Calm by Anna Maria Vacations Home in Holmes Beach, Florida VPR16-000304 Welcome to Stay Calm, a beautiful gro ...
From $507 per night (USD)VRBO
From $291 per night (USD)Expedia
Canal Front Home with Boat Dock and Private Pool! Short Walk to the Beach! - Vil
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Sandpiper by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000743 Welcome to Villa Sandpiper, a s ...
From $291 per night (USD)Expedia
From $410 per night (USD)VRBO
Vacation Home with Private Pool and Ping Pong Table! Short Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Florence by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000355 Welcome to Villa Florence, a magnif ...
From $410 per night (USD)VRBO
From $284 per night (USD)Expedia
AMI Escape! King Suite, Twin Room and Ping Pong Near Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Castaway Cottage by Anna Maria Vacations Home in Holmes Beach, Florida VRC17-000189 Welcome to Castaway Cottage, a t ...
From $284 per night (USD)Expedia
From $320 per night (USD)VRBO
Beachfront Condo with Private Balcony and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf Sands #102 by Anna Maria Vacations Condo in Holmes Beach, Florida VRC16-000363 Welcome to Gulf Sands #102, a ch ...
From $320 per night (USD)VRBO
From $479 per night (USD)Expedia
AMI Home with Heated Pool! 6 Minute Walk to Beach! - Egrets Nest
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Egrets Nest by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000610 Welcome to Egrets Nest, a beauti ...
From $479 per night (USD)Expedia
From $644 per night (USD)VRBO
Canal front home with Incredible Rooftop Views and Pool with Spa - Aqua Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Aqua Bay by Anna Maria Vacations Home in Holmes Beach, Florida Aqua Bay is a luxurious canal-front retreat boasting f ...
From $644 per night (USD)VRBO
From $337 per night (USD)Expedia
AMI Escape! Direct Beach Access, Gulf Views and Walk to Holmes Beach Shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf Shores #106 by Anna Maria Vacations Condo in Holmes Beach, Florida VRC16-000081 Welcome to Gulf Shores #106, a ...
From $337 per night (USD)Expedia
From $289 per night (USD)VRBO
Beach Home with Pool and Gas Grill! 2 min walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tiki Sunrise by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC19-000045 Welcome to Tiki Sunrise, a delightf ...
From $289 per night (USD)VRBO
From $252 per night (USD)Expedia
Buckeye Haven - Beachfront Community with Tennis, and Pickleball Courts!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Buckeye Haven is situated in the sought after community of Playa Encantada on Anna Maria Island. Come enjoy this tropica ...
From $252 per night (USD)Expedia
From $410 per night (USD)VRBO
Beachfront - Hidden Cove Unit 5 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing views from the living room and primary bedroom of this 2 bedroom/2.5 bathroom. Take a drink outside and sit on y ...
From $410 per night (USD)VRBO
From $480 per night (USD)VRBO
Waterfront Condo on Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to paradise! The Westbay Point and Moorings complex is a private and spacious waterfront community offering an ...
From $480 per night (USD)VRBO
From $317 per night (USD)VRBO
Beachfront Bliss with Gulf Views & Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Property Highlights • Beachfront resort-style condo on Holmes Beach • Two private balconies with Gulf and pool views ...
From $317 per night (USD)VRBO
From $426 per night (USD)Expedia
5 Minute Short Walk To Beach, Shops and Restaurants - Single Level Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Recently renovated with a brand-new kitchen, bathrooms, and all new furniture! Welcome to Blue Bella on Anna Maria Isla ...
From $426 per night (USD)Expedia
From $380 per night (USD)VRBO
Aquamarine Oasis by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Aquamarine Oasis is an exquisite vacation home located just steps away from the pristine white sands and turquoise water ...
From $380 per night (USD)VRBO
From $311 per night (USD)Expedia
Beachfront Condo on AMI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located just steps away from the white s ...
From $311 per night (USD)Expedia
From $511 per night (USD)VRBO
New Listing! Luxury 4BR Canal Home with Pool. Monthly Rental.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Royale Serenity! This 4BR/3BA spacious canal home with a large inground pool and spa is the perfect family g ...
From $511 per night (USD)VRBO
From $249 per night (USD)VRBO
Anna Maria Island Gulf View, Steps to Beach, 2br/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully furnished 2br/2ba gulf view condo steps to the beach, in Holmes Beach on Anna Maria Island. Walk to dining, ...
From $249 per night (USD)VRBO
From $313 per night (USD)VRBO
Paradise - Steps to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Super location in the center of Holmes Beach! Park the car as you are just steps to the beautiful beach, fantastic resta ...
From $313 per night (USD)VRBO
From $485 per night (USD)VRBO
Tarpon House-Luxury 4/4 Home on Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
What You'll Love About This Home: Location! 3 Blocks to the Beach! 4 Bedrooms / 4 Bathrooms 3 King Beds, Two Sets of Bu ...
From $485 per night (USD)VRBO
From $260 per night (USD)VRBO
Beautiful, Great location, Walk to everything, 2Bdrm 2Bdrm, Private,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided - sleeps 4, 2 bedroom/2 bath, very privat ...
From $260 per night (USD)VRBO
From $443 per night (USD)Expedia
Sandpiper Villa! 3BR with Heated Pool, Balcony and Walk to Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sandpiper Villa by AMI Locals VRC23-000136 Welcome to Sandpiper Villa, a three bedroom, two bath vacation rental locat ...
From $443 per night (USD)Expedia
From $540 per night (USD)VRBO
Luxury Gulf-Front Condo w/ Balcony Views | 3BR/2BA | Pool | Beach Access | Sleeps 6 | Great Sunsets | Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the ultimate beach getaway in this beautifully remodeled 3-bedroom, 2-bath Gulf-front condo on Anna Maria Isl ...
From $540 per night (USD)VRBO
From $408 per night (USD)Expedia
Gorgeous 1 Bed Condo! Beachside with Shared Pool, Near Shops!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts Poolside #115 by AMI Locals VRC16-000672 Welcome to Coconuts Poolside #115, a charming one-bedroom, one-ba ...
From $408 per night (USD)Expedia
From $500 per night (USD)VRBO
3 Bedroom, 2 Bath Ground Level with Heated Pool - Short walk to the beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Crab Shack with an open concept living area. The kitchen is fully furnished with microwave, toaster oven, ...
From $500 per night (USD)VRBO
From $398 per night (USD)Expedia
Barefoot Bliss by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Barefoot Bliss is a laid-back, ground-level retreat designed for easy island living, with an updated kitchen, refreshed ...
From $398 per night (USD)Expedia
From $571 per night (USD)VRBO
The Sweet Spot: Loaded with Games, Pool Side Lounge, Mini Golf
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Sweet Spot by Anna Maria Life Vacation Rentals 7402 Marina Drive, Holmes Beach, FL 34217 What You'll Love About Thi ...
From $571 per night (USD)VRBO
From $667 per night (USD)Expedia
Bubbles Up by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your island escape awaits at this vacation paradise inspired by the laid-back vibes of a Jimmy Buffett melody. *Feature ...
From $667 per night (USD)Expedia
From $523 per night (USD)VRBO
Ocean Views - Spacious Unit with Bonus Loft & SwimSpa
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Private Hot Tub Direct Beach Access Amazing Ocean View Bonus Loft! Welcome to "A Wave From It All" – your perfect retre ...
From $523 per night (USD)VRBO
From $258 per night (USD)Expedia
2 Bedrooms with Hot Tub - Steps from Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Castaway Cove, your relaxing home base on Anna Maria Island. Just steps from the beach and packed with everyt ...
From $258 per night (USD)Expedia
From $244 per night (USD)VRBO
2 Bedroom End Unit, Hot Tub, Parking, - Steps from the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Steps From The Beach!! Shared Hot Tub! Private Parking Included! End Unit! Welcome to Dune Our Thing, your relaxing bea ...
From $244 per night (USD)VRBO
From $420 per night (USD)Expedia
Anna Maria Gulf Beach Place Just Steps TO The Edge OF The Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This gorgeous Fully Remodeled 1300 sq ft 2 Bedroom 2 Bath condo, located on just steps to the beach. Gulf Beach Place is ...
From $420 per night (USD)Expedia
From $715 per night (USD)VRBO
No R-Egrets:1 Block to Beach! Pool Game Room by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
No R-Egrets by Anna Maria Life Vacation Rentals 127th 50th St, Holmes Beach, FL 34217 What You'll Love About This Home: ...
From $715 per night (USD)VRBO
From $481 per night (USD)Expedia
Beachfront, Breathtaking Gulfviews with Resort Pool and Spectacular Sunsets.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beachfront condo with stunning ocean views, manicured grounds and swaying palms. This lovely, recently renovated, end ...
From $481 per night (USD)Expedia
From $381 per night (USD)VRBO
Beautiful New Pool/Spa, Steps to Sand & Restaurants, Golf Cart Included
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beach lovers, this updated cottage is just a 5‑minute walk to the sand and close to great restaurants and shops. Enjoy a ...
From $381 per night (USD)VRBO
From $263 per night (USD)Expedia
Pelican Place at The Nautilus · Tennis & Pickleball · Steps to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC24-000057 2BR · 2BA · Sleeps 4 · Steps to Gulf · Two King Beds · Heated Pool · Tennis · Pickleball · Updated Kitchen ...
From $263 per night (USD)Expedia
From $549 per night (USD)VRBO
My Grand Floridian: Canal Front, Dock, Pool, Games by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
My Grand Floridian by Anna Maria Life Vacation Rentals 207 N Harbor Dr, Holmes Beach, FL, 3427 What You'll Love About T ...
From $549 per night (USD)VRBO
From $448 per night (USD)Expedia
Elevator - Costa Lotta by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Costa Lotta is "home away from home”. All the amenities you will need in this 2,100 sq.ft. home. Costa Lotta is the per ...
From $448 per night (USD)Expedia
From $387 per night (USD)VRBO
Spacious Oasis - 3BR Pool Home - By Island Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Spacious Oasis! Spacious Oasis is a Mediterranean style 3-bedroom, 3-bathroom pool home located just blocks a ...
From $387 per night (USD)VRBO
From $567 per night (USD)Expedia
Day Dream: Pool, Spa, Waterslide, 1.5 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
207 77th St, Holmes Beach, FL 34217 What You'll Love About This Home: Location! 1.5 Blocks to the Beach! 4 Bedrooms / 4 ...
From $567 per night (USD)Expedia
From $400 per night (USD)VRBO
Great location on Holmes Beach! 2 bdrm Condo Steps to the Beach! Heated pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly Furnished and renovated! Steps to the Beach! 2 Bdrm 2 bath Condo - shared heated pool Island Life Suites is centr ...
From $400 per night (USD)VRBO
From $563 per night (USD)Expedia
My Big Fat Beach House: Putt-Putt, Ping Pong, Heated Pool, Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to the sandy shores of Anna Maria Island and uncover the hidden gem that is "My Big Fat Beach House". This sprawl ...
From $563 per night (USD)Expedia
From $298 per night (USD)VRBO
Island 🏝️ Escape on Private Street – 5 min Walk to Beach & Dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to this stunning beach house, just steps away from the sugary sand beaches of Anna Maria Island! This gem is not ...
From $298 per night (USD)VRBO
From $446 per night (USD)Expedia
Cheeky Chateau – 4BR Pool Home in Holmes Beach, Anna Maria Island, FL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Cheeky Chateau, a 4-bedroom, 3-bathroom vacation rental in Holmes Beach on Anna Maria Island, featuring a pri ...
From $446 per night (USD)Expedia
From $169 per night (USD)VRBO
Cottage Near the Beach with Paddleboards and More! - A Lil' Nauti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A Lil’ Nauti by Anna Maria Vacations Condo in Holmes Beach, Florida VRC23-000061 Welcome to A Lil’ Nauti, a charming gr ...
From $169 per night (USD)VRBO
From $587 per night (USD)Expedia
Octopus Cottage: 1.5 Blocks to Beach, Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Octopus Cottage by Anna Maria Life Vacation Rentals 209 69th St, Holmes Beach, FL 34217 What You'll Love About This Hom ...
From $587 per night (USD)Expedia
From $367 per night (USD)VRBO
Sunday Funday managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
🌞 Sunday Funday – Your Perfect Beachside Getaway on Anna Maria Island 📍517 42nd St, Holmes Beach, FL 34217 🪪 VRC22-00 ...
From $367 per night (USD)VRBO
From $301 per night (USD)Expedia
7310 Holmes - Duplex 1 Bedroom / 1 Bath , maximum occupancy of 4 people.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
7310 Holmes Boulevard, Unit B - Anna Maria Island - Duplex - 1 Bedroom / 1 Bath, maximum occupancy of 4 people. Vrc16-00 ...
From $301 per night (USD)Expedia
From $223 per night (USD)VRBO
Anna Maria's Dream: Ground level, close to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
***Photos Updated July 2025*** Welcome to Anna Maria's Dream, your perfect getaway on beautiful Anna Maria Island. This ...
From $223 per night (USD)VRBO
From $531 per night (USD)Expedia
Splash of Lime by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Splash of Lime! This stunning, 3-bedroom, 2-bathroom pool home has 1,438 square feet of elevated living space ...
From $531 per night (USD)Expedia
From $369 per night (USD)VRBO
Beachfront..Island Beach Club - Gorgeous First Floor 2 Bed, 2 bath with Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this newly Updated, Spacious First Floor Condo located on the beach. You have private beach access and a beautifu ...
From $369 per night (USD)VRBO
From $211 per night (USD)VRBO
White Pelican - 1000 Feet to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to The White Pelican, your charming retreat on Anna Maria Island! Nestled just 1000 feet from the pristine sands ...
From $211 per night (USD)VRBO
From $746 per night (USD)VRBO
Beachfront Paradise 110 ~ Yes, That'S Your View! ~ Specials ~
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beachfront Paradise 110 is a beautiful Beachfront 1 bedroom retreat located directly on the Gulf of Mexico! This welcomi ...
From $746 per night (USD)VRBO
From $346 per night (USD)Expedia
Family Home with Private Pool, 3 mins from Beach! - Ariel's by the Sea
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ariel’s by the Sea by AMI Locals VRC18-000079 Welcome to Ariel's by the Sea, a luxury ground-level vacation home just ...
From $346 per night (USD)Expedia
From $339 per night (USD)VRBO
Coastal Ground-Level Home with Private Pool! Steps from the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
My Island Paradise by AMI Locals Welcome to My Island Paradise, a charming 3-bedroom, 2-bathroom ground-level vacation ...
From $339 per night (USD)VRBO
From $451 per night (USD)Expedia
North Beach Paradise by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to North Beach Paradise - a 3BD/2BA Key West, Island style townhouse on Holmes Beach! It's located in a quiet a ...
From $451 per night (USD)Expedia
From $214 per night (USD)VRBO
Pelican Paradise by A Shore Thing Vacations!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Pelican Paradise! This 2 bedroom condo is close to the beach and in the heart of it all. 🏡 Property Highlig ...
From $214 per night (USD)VRBO
From $584 per night (USD)Expedia
Aqua Vista by Duncan Real Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Aqua Vista! This beautiful, centrally located 4-bedroom, 3.5-bathroom pool home has 2,326 square feet of elev ...
From $584 per night (USD)Expedia
From $258 per night (USD)VRBO
Beachside Pointe by A Shore Thing Vacations!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beachside Pointe! This sparkling clean and bright 2 bedroom condo is close to the beach and in the heart of i ...
From $258 per night (USD)VRBO
From $1227 per night (USD)Expedia
Seaside Haven by Duncan Real Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Seaside Haven is an elegant Island property that promises an unforgettable experience. The 4 bedroom and 3 1/2 bath pool ...
From $1227 per night (USD)Expedia
From $409 per night (USD)VRBO
Americana AMI Lighthouse 3BR w/pool + rooftop deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Lighthouse by AMIBeachClub Discover this unique lighthouse vacation rental w/private pool on Anna Maria Island. The ...
From $409 per night (USD)VRBO
From $402 per night (USD)Expedia
Family vacation on AMI w/pool 4BR, 2.5BA, up to 8 guests
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Gables by AMIBeachClub Unwind at this colonial inspired beach house with private pool. The Gables has 4 bedrooms, 2. ...
From $402 per night (USD)Expedia
From $220 per night (USD)VRBO
Beach Escape By Coastal Chic Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Beach Escape, a beautifully remodeled 2-bedroom, 2-bathroom haven just 1/2 block from the pristine white sand ...
From $220 per night (USD)VRBO
From $348 per night (USD)Expedia
Tipsy Turtle: 2 Houses to Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tipsy Turtle by Anna Maria Life Vacation Rentals 104 43rd, Holmes Beach, FL 34217 What You'll Love About This Home: Loc ...
From $348 per night (USD)Expedia
From $464 per night (USD)VRBO
Gigi & Poppy’s Paradise: Pool, Gulf Views, Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Gigi & Poppy's Paradise in Holmes Beach on Anna Maria Island! This comfortable 4-bedroom, 3-bathroom home is ...
From $464 per night (USD)VRBO
From $372 per night (USD)Expedia
Spacious Coastal Oasis: Enjoy Three King Beds & Room for Everyone!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newest addition, Salt Cottage, located just 2 blocks from the Gulf beaches of Anna Maria Island! This cot ...
From $372 per night (USD)Expedia
From $156 per night (USD)VRBO
Beachy Butterfly! Poolside Holmes Beach Stay!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beachy Butterfly by Anna Maria Vacations Condo in Holmes Beach, Florida VRC24-000089 Welcome to Beachy Butterfly, a c ...
From $156 per night (USD)VRBO
From $260 per night (USD)Expedia
Latitude Adjustment by A Shore Thing Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Latitude Adjustment! Escape to this tranquil 2-bedroom condo on beautiful Anna Maria Island, just a short wal ...
From $260 per night (USD)Expedia
From $241 per night (USD)VRBO
Canal-Front Home with Dock and Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Salty Soul by Anna Maria Island Accommodations Welcome to Salty Soul, your family’s canal-front island escape located ...
From $241 per night (USD)VRBO
From $266 per night (USD)Expedia
Charming 2-bedroom condo with WiFi, AC in serene Holmes Beach Walk to the beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay comfortably in Holmes Beach at this 2-bedroom condo. With a king bed and a full bed, guests can relax in this aweso ...
From $266 per night (USD)Expedia
From $437 per night (USD)VRBO
Pool, Bikes & BBQ Included! 2min to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Top Reasons to Book The Cranes Nest: - Prime Holmes Beach Location on Anna Maria Island - 3 Bedrooms · 3 Bathrooms · 3 S ...
From $437 per night (USD)VRBO
From $365 per night (USD)Expedia
AMI's Salty Breeze: 5-min walk to Beach, community pool, relaxing decor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to AMI's Salty Breeze, your perfect central getaway on Anna Maria Island! This 3-bedroom, 2-bathroom townhouse i ...
From $365 per night (USD)Expedia
From $1428 per night (USD)VRBO
Family-Friendly Waterfront Paradise!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Coral Castle by AMI Locals VRC16-000158 Welcome to Coral Castle, a luxurious waterfront retreat in the heart of Anna M ...
From $1428 per night (USD)VRBO
From $514 per night (USD)Expedia
Hav'Anna Daydreamin': Pool, 1 Block to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hav'Anna Daydreamin' by Anna Maria Life Vacation Rentals 204 Archer Way, Anna Maria, FL 34216 What You'll Love About Th ...
From $514 per night (USD)Expedia
From $459 per night (USD)VRBO
LaPlage 3 · Beachfront · Pool · Elevator
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
VRC24-000103 3BR · 3BA · Sleeps 6 · Direct Beachfront · Elevator · Pool & Gulf Balcony · Two King Beds · Twin Room · Gr ...
From $459 per night (USD)VRBO
From $296 per night (USD)Expedia
AMI Beach Days & Island Nights with a pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Property Highlights • Walk to the beach, restaurants & shopping • 2 Bedrooms | 2 Bathrooms | Sleeps 6 • King primary ...
From $296 per night (USD)Expedia
From $221 per night (USD)VRBO
Island Delight: Pool Spa Dog Friendly by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Island Delight by Anna Maria Life Vacation Rentals 424 62nd St, Holmes Beach, FL 34217 What You'll Love About This Home ...
From $221 per night (USD)VRBO
From $323 per night (USD)Expedia
Swept Away B · EV Charger · Fenced Pool · Renovated 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC25-000116 2BR · 2BA · Sleeps 6 · Private Fenced Heated Pool · EV Charger Included · 2025 Renovation · 6-Min Walk to ...
From $323 per night (USD)Expedia