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

Anna Maria Rentals

From $539 per night (USD)
VRBO
Seaside Beach House 205 Gulf Front Condo Pool Unforgettable Sunset Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
VRC16-000508 You will enjoy this gulf front condominium on Florida's Anna Maria Island. This is a smoke free two bedroo ...
From $539 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Two Bedroom Cozy Island Home Right Around the Corner from Gulf Beaches. Lots of Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Loggerhead Beach House just a few houses from the Gulf beaches on Anna Maria Island. Loggerhead Beach House i ...
From $434 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Beautiful cottage just around the corner from the beach with Private Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Seahorse Beach House located just a few houses from the Gulf beaches of Anna Maria Island. Seahorse Beach Hou ...
From $452 per night (USD)
VRBO
From $367 per night (USD)
Expedia
Ground Floor Cottage with 2 Master Suites and Private Heated Pool - Close to Beach!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Castaway Cottage located 2 houses down from the Gulf beaches of Anna Maria Island. Castaway Cottage is a grou ...
From $367 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Two Bedroom Ground Floor Island Home Sleeps 5 and Includes Heated Pool.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to the Sand Dollar Shack located just a few houses from the Gulf beaches on Anna Maria Island. The Sand Dollar S ...
From $452 per night (USD)
VRBO
From $1266 per night (USD)
Expedia
Silver Surf- A stunning family home 2 blocks from the beach.
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
The minute you walk in the front door at Silver Surf you'll be convinced that you're about to experience the very best o ...
From $1266 per night (USD)
Expedia
$217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...$
From $254 per night (USD)
VRBO
217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC#20-000113 Private Poo ...
From $254 per night (USD)
VRBO
$Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide$
From $1127 per night (USD)
Expedia
Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Sands of Time 6908 Holmes Blvd Holmes Beach, FL 34217 Sands of Time is a newly built 6 bedroom, 4.5 bathroom vacation ...
From $1127 per night (USD)
Expedia
From $716 per night (USD)
VRBO
AM I Dreaming: Heated Pool, Family Friendly Home, 3-min walk to beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The vacation you have imagined finally becomes a reality. AM I dreaming is a bright and charming 3 bedroom, 2 bathroom c ...
From $716 per night (USD)
VRBO
From $800 per night (USD)
Expedia
Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66t ...
From $800 per night (USD)
Expedia
From $497 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 $497 per night (USD)
VRBO
$Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...$
From $408 per night (USD)
Expedia
Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Walk 313 - Anna Maria Island - Townhouse - 3 Bedroom/ 2 .5 Bath, maximum occupancy of 6 people. VRC16-000052 ...
From $408 per night (USD)
Expedia
From $650 per night (USD)
VRBO
Florida Breeze: Pool home in perfect central location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Florida Breeze is the perfect vacation rental for your next trip to Anna Maria Island! The location with the short walk ...
From $650 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Seaside Beach House 203 | Gulf-Front Escape with Panoramic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
VRC20-000296 Wake up to breathtaking Gulf views and fall asleep to the sound of the waves at Seaside Beach House 203, a ...
From $398 per night (USD)
Expedia
Click For Pricing
VRBO
Beach Bay Serenity: Pine Ave canal front pool home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you enjoy salt air and sea breezes, morning coffee on your patio, walking miles and miles of white sandy beach and sw ...
Click For Pricing
VRBO
$Turtle Nest! New Holiday House w\/ Pool, Wifi, and Access to the Beach$
From $586 per night (USD)
VRBO
Turtle Nest! New Holiday House w\/ Pool, Wifi, and Access to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Remodeled in 2025, this comfortable and tastefully furnished home offers everything you need for a relaxed vacation with ...
From $586 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Home with Private Outdoor Living Space, Community Pool - Sea La Vie
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea La Vie by AMI Locals Condo in Holmes Beach, Florida VRC21-000203 Welcome to Sea La Vie! This three-bedroom, three- ...
From $382 per night (USD)
VRBO
From $977 per night (USD)
Expedia
Sweet Retreat Cottage: Ground level cottage across the street from the beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This Anna Maria Island rental was given the name Sweet Retreat Cottage for a reason. Offering a private heated pool, vie ...
From $977 per night (USD)
Expedia
From $827 per night (USD)
VRBO
Golf Cart, Salty Shamrock by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be ov ...
From $827 per night (USD)
VRBO
From $751 per night (USD)
Expedia
Gulf Front 1 Bedroom Condo - Amazing Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Coconuts Beachfront #112 Condo in Holmes Beach, Florida VRC21-000175 Your dream beach vacation awaits at Coconuts Beach ...
From $751 per night (USD)
Expedia
$Mango Bay – Luxury 4BR w\/ Heated Pool, Spa & Game Room$
From $843 per night (USD)
VRBO
Mango Bay – Luxury 4BR w\/ Heated Pool, Spa & Game Room
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) 3,000 sqft of a Beautifully Restored Island Home with Poo ...
From $843 per night (USD)
VRBO
From $701 per night (USD)
Expedia
Beachfront - Sandy Turtle by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers pictures ...
From $701 per night (USD)
Expedia
$Coconuts108 - GULFFRONT - 1BR\/1BA with pool - By Island Real Estate Vacations$
From $556 per night (USD)
VRBO
Coconuts108 - GULFFRONT - 1BR\/1BA with pool - By Island Real Estate Vacations
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
“The Coconuts Beach Resort 108” is a 1 bed 1 bath beach front condo, nestled in the heart of Holmes Beach. Apart of the ...
From $556 per night (USD)
VRBO
From $362 per night (USD)
Expedia
A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly furnished ground level home is ...
From $362 per night (USD)
Expedia
From $1005 per night (USD)
VRBO
2nd floor Condo with Beach and Pool Access - Coconuts Gulf View #118
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coconuts Gulf Views #118 by AMI Locals Condo in Holmes Beach, Florida VRC21-000172 Let the good times roll at Coconu ...
From $1005 per night (USD)
VRBO
$BEACH FRONT, 2 Bd\/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets$
From $476 per night (USD)
Expedia
BEACH FRONT, 2 Bd\/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
**ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom ...
From $476 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Vibrant retreat with pool, beach access, tennis, balcony, & stunning ocean views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Place 19 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $524 per night (USD)
VRBO
$Lakeside Beach House 3\/2 Pool Home Outdoor Kitchen Close to Beach$
From $486 per night (USD)
Expedia
Lakeside Beach House 3\/2 Pool Home Outdoor Kitchen Close to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC16-000807 The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private heated ...
From $486 per night (USD)
Expedia
$March Dates! Ground Floor Luxury Home, Heated Pool\/Spa 🌴🌴🌴🌴$
From $742 per night (USD)
VRBO
March Dates! Ground Floor Luxury Home, Heated Pool\/Spa 🌴🌴🌴🌴
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Ground Floor Luxury Home with Heated Pool/Spa, very close to Beach 🌴🌴🌴🌴 Welcome to the AMI Beach Home on beautiful ...
From $742 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Breezy house with great location near beach, shopping & dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Guava Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $290 per night (USD)
Expedia
From $1287 per night (USD)
VRBO
Buena Vista #2: Luxury Beach Front Condo, Amazing Views, Pool by Anna Maria Life Vacation Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Buena Vista #2 by Anna Maria Life Vacation Rentals 101 67th St #2, Holmes Beach, FL 34217 What You'll Love About This H ...
From $1287 per night (USD)
VRBO
From $414 per night (USD)
Expedia
Luxury Beach House, 1 Block from beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming Anna Maria Island Vacation Home is located just a few houses from the white sand beaches! Holmes Beach is ...
From $414 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Casual beachside getaway with pool, and easy beach access
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Water's Edge 105 South Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $435 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Welcoming condo close to the beach with private heated pool & WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
LaMadeira 305 Unit A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $457 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Upscale condo with large deck & shared pool - just steps from the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
La Casa Karen Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $492 per night (USD)
VRBO
$Cheerful condo with patio & pool\/tennis - walk a few steps to the beach$
From $445 per night (USD)
Expedia
Cheerful condo with patio & pool\/tennis - walk a few steps to the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nautilus 105 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $445 per night (USD)
Expedia
From $942 per night (USD)
VRBO
BUENA VISTA LUXURY BEACHFRONT 4BR - Anna Maria Island - By Island Real Estate Va
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Top 10 Gulfview on Anna Maria Island!!! You can see for miles in both direction down the beach. Luxury condominium “Buen ...
From $942 per night (USD)
VRBO
From $1694 per night (USD)
Expedia
DIRECT BEACH FRONT - Luxury 4BR Condo - Anna Maria Island- By Island Real Estate
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
DIRECT BEACH FRONT - Luxury 4BR Condo - Buena Vista #3 - 101 67th Street - 4 Bedrooms and 3 and a 1/2 Baths - Bed/s: 3 ...
From $1694 per night (USD)
Expedia
From $789 per night (USD)
VRBO
Home near the Beach. SUP Paddleboards, Large Private Pool - Pure Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Pure Beach by Anna Maria Island Locals Home in Holmes Beach, FL VRC21-000101 Welcome to Pure Beach, a luxurious three- ...
From $789 per night (USD)
VRBO
From $349 per night (USD)
Expedia
One Bedroom Island Luxury Cottage located less than 2 blocks from the beach.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Flop Cottage located 1 block from the Gulf beaches of Anna Maria Island. Flop Cottage is a ground level half ...
From $349 per night (USD)
Expedia
From $1233 per night (USD)
VRBO
Beach Front Home on Anna Maria Island - Great Views! Pool! Sleeps 10!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Experience Anna Maria Island at its best! This luxury beach-front home located in Holmes Beach is in the monthly rental ...
From $1233 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The cozy front porch of Gulf Winds B invites you to have your morning coffee or your evening cocktail and in the back ya ...
From $274 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Barefoot Dreams: Dog Friendly, Private Pool,1 Block to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Barefoot Dreams by Anna Maria Life Vacation Rentals 201 76th St. East Unit B, Holmes Beach, FL 34217 What You'll Love A ...
From $341 per night (USD)
VRBO
From $379 per night (USD)
Expedia
2 minute walk to the beach! Off the main road in a quiet and tropical setting
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
What you'll love about this home: - Location! 2 min walk to the beach - 3 Bedrooms / 2 full bathrooms - 1 King, 1 Que ...
From $379 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Weekly Discounts! Exceptional Rating-A Pearl of a Beach Home- private pool & spa
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Tropical rear yard with private luxury heated Saltwater pool and hot tub/spa and spacious paved area plus large ground f ...
From $412 per night (USD)
VRBO
From $537 per night (USD)
Expedia
Easy walk to beach, enjoy private splash pool, super clean!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Custom built this three bedroom, two bath home is beautifully designed for six guests. Come to Island Breeze and relax w ...
From $537 per night (USD)
Expedia
From $832 per night (USD)
VRBO
Beautiful home with fenced yard, heated pool, hot tub, and elevator!
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Sand Castle by Anna Maria Island Accommodations Holmes Beach, FL 34217 VRC19-000022 Welcome to Sand Castle! Nestled in ...
From $832 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Beautiful home near the beach with heated pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Highlights • Less than a five-minute walk to the beach • Private pool • Washer and dryer • Less than a 10-minute troll ...
From $455 per night (USD)
Expedia
From $556 per night (USD)
VRBO
Family Home with Pool Near Gulf Beaches - Corona Joe's Beach Cottage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Corona Joe's Beach Cottage by AMI Accommodations Home in Holmes Beach, FL VRC17-000163 Experience the perfect family g ...
From $556 per night (USD)
VRBO
$Beautiful, Ground Level 4 bedroom\/3 bath home, just a short block to the beach$
From $808 per night (USD)
Expedia
Beautiful, Ground Level 4 bedroom\/3 bath home, just a short block to the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Simply Chic 1.5 Blocks to Beach Beautiful, Ground Level 4 bedroom/3 bath home, just a short block to the beach. Beaut ...
From $808 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Home with Private Backyard and Heated Pool - Gulf Breeze Villa B
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gulf Breeze Villa B by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC16-000146 Gulf Breeze Vill ...
From $350 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Your Own Oasis: A Tropical Retreat with Lagoon Style Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Own Oasis - An Island Retreat with Lagoon Style Pool, close to Bay and Beach Escape to "Your Own Oasis" on Anna Ma ...
From $442 per night (USD)
Expedia
$2 Bedroom \/ 2 Bath Ground Level With a Heated Pool$
From $306 per night (USD)
VRBO
2 Bedroom \/ 2 Bath Ground Level With a Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This listing is for a Weekly rental located in the heart of Anna Maria Island at 305 61st St, Unit A, Holmes Beach, FL, ...
From $306 per night (USD)
VRBO
From $453 per night (USD)
Expedia
Coastal home with pool and tropical landscaping!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Pineapple Palms by AMI Accommodations Holmes Beach, FL 2.5 Blocks to Beach Highlights: • Private heated pool • Beaut ...
From $453 per night (USD)
Expedia
From $839 per night (USD)
VRBO
1.5 Blocks to Gulf Beaches, Private Heated Pool - No Bad Days
Bedrooms:
3
Bathrooms:
5
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 $839 per night (USD)
VRBO
From $538 per night (USD)
Expedia
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 $538 per night (USD)
Expedia
From $600 per night (USD)
VRBO
Enjoy Endless Summer Fun with a Private Heated Pool at Key Largo Cottage!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Key Largo Cottage by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 Discover your ultimate family g ...
From $600 per night (USD)
VRBO
From $628 per night (USD)
Expedia
Anna Maria Island Beach Cottage with Private Pool and Spa
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beach Cottage by Anna Maria Island Accommodations Home in Holmes Beach, FL 1 Block to beach Highlights: • Heated poo ...
From $628 per night (USD)
Expedia
From $587 per night (USD)
VRBO
Centrally located. 3 blocks to the beach. Private pool and hot tub.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Sand Dollar by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC16-000117 Welcome to Sand Dollar, a ...
From $587 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Private home with Pool, Spa, and Ping Pong! 6 mins to Beach! - Banana Cabana
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Banana Cabana by Anna Maria Island Accommodations 318 64th St Holmes Beach, FL 34217 Relaxation awaits at Banana Caba ...
From $669 per night (USD)
Expedia
From $295 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 $295 per night (USD)
VRBO
From $1182 per night (USD)
Expedia
Barefoot Bungalow:Dog Friendly, Screened Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Barefoot Bungalow by Anna Maria Life Vacation Rentals 213 70th St., Holmes Beach, FL 34217 What You'll Love About This ...
From $1182 per night (USD)
Expedia
From $382 per night (USD)
VRBO
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 $382 per night (USD)
VRBO
$Beautiful lakeside home w\/ upscale amenities, heated private pool & fishing dock$
From $487 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 $487 per night (USD)
Expedia
From $430 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 $430 per night (USD)
VRBO
From $495 per night (USD)
Expedia
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 $495 per night (USD)
Expedia
From $448 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 $448 per night (USD)
VRBO
From $298 per night (USD)
Expedia
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 $298 per night (USD)
Expedia
From $494 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 $494 per night (USD)
VRBO
From $179 per night (USD)
Expedia
Seaside family-friendly condo with WiFi, pool & prime location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Serenity Now Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $179 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Comfortable island villa with private heated pool, courtyard & easy beach access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Blue Wave Villa East Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $404 per night (USD)
VRBO
$Spacious dog-friendly home w\/ heated private pool, a few blocks from the beach$
From $1107 per night (USD)
Expedia
Spacious dog-friendly home w\/ heated private pool, a few blocks from the beach
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Almost Gulf Front Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1107 per night (USD)
Expedia
$Tropical-themed getaway w\/ heated private pool - walk to free trolley, shopping$
From $410 per night (USD)
VRBO
Tropical-themed getaway w\/ heated private pool - walk to free trolley, shopping
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $410 per night (USD)
VRBO
From $519 per night (USD)
Expedia
Waterfront home with heated pool + spa, patio, grill, & free WiFi - dog-friendly
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
3 Oars Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $519 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Island-style townhome with WiFi & pool - minutes from the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
North Beach Village 27 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $448 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Island Time: Gulf front condo 20 ft to the beach with shared pool
Bedrooms:
2
Bathrooms:
2
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 $388 per night (USD)
Expedia
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VRBO
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 Pricing
VRBO
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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 Pricing
Expedia
From $638 per night (USD)
VRBO
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 $638 per night (USD)
VRBO
From $806 per night (USD)
Expedia
Perfect 1-bedroom Beachfront Getaway!! See the sunsets and feel the breeze!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Highlights: -large bay of windows perfectly frame the beach from the kitchen, living, and dining areas -Screened porch - ...
From $806 per night (USD)
Expedia
From $429 per night (USD)
VRBO
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 $429 per night (USD)
VRBO
From $590 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 $590 per night (USD)
Expedia
From $440 per night (USD)
VRBO
3 bedroom, on AMI, 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 $440 per night (USD)
VRBO
From $1266 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 $1266 per night (USD)
Expedia
From $346 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 $346 per night (USD)
VRBO
$Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico$
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Expedia
Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
NOTE: the elevator at this property are currently not available. Imagine waking up every morning to a million dollar v ...
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Expedia
From $478 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 $478 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Island Hideaway East: 5 Minute Walk to Beach, Private Pool by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Island Hideaway East by Anna Maria Life Vacation Rentals 308B 67th St., Holmes Beach, FL 34217 What you'll love about t ...
From $524 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Perfect Family Vacation home just off the beach! Private Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Hideaway by AMI Locals Home in Holmes Beach, FL Features: • Private heated pool • Ground-level home, very access ...
From $408 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Golf Cart, Island Haven by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
6 PERSON GOLF CART INCLUDED ON ALL RESERVATIONS THAT CHECK OUT BEFORE 1/3/26 All Drivers must be over the age of 21. Dri ...
From $601 per night (USD)
Expedia
From $603 per night (USD)
VRBO
Sea Breeze: Pool home in perfect central location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3 bed 2 bath island oasis will take you back to the days of old Florida charm, but in a modern and well appointed s ...
From $603 per night (USD)
VRBO
$Blue Haven Beach House - 3BR Coastal Retreat w\/ Heated Pool, Gulf Views & Steps to the Beach$
From $658 per night (USD)
Expedia
Blue Haven Beach House - 3BR Coastal Retreat w\/ Heated Pool, Gulf Views & Steps to the Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Welcome to Blue Haven Beach House! On Anna Maria Island (Holmes Beach, FL) Discover island charm and modern comforts at ...
From $658 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Luxury home in the perfect location, 2 blocks to beach - Island Princess
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Island Princess by AMI Locals Home in Holmes Beach, FL VCR19-000296 Welcome to Island Princess! This stunning custom-b ...
From $309 per night (USD)
VRBO
From $2634 per night (USD)
Expedia
Luxury home just steps away from the beach with pool, spa & rooftop!
Bedrooms:
7
Bathrooms:
8
Sleeps:
14
The Ritz by Anna Maria Island Locals Home in Holmes Beach, FL Highlights: • Rooftop deck • Heated pool and spa • Coffee ...
From $2634 per night (USD)
Expedia
From $640 per night (USD)
VRBO
Putting Green - Flip Flops Forever by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the ...
From $640 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Pet-Friendly - Rum Dog by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
3
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 $289 per night (USD)
Expedia
From $196 per night (USD)
VRBO
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 $196 per night (USD)
VRBO
From $989 per night (USD)
Expedia
Blue Palm Paradise: Dog friendly, Pool, 3 Minute Walk to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
4
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 $989 per night (USD)
Expedia
$GULF FRONT Beautiful Condo w\/Heated Pool, FREE WiFi & Trolley, Great Sunsets!$
From $511 per night (USD)
VRBO
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 $511 per night (USD)
VRBO
From $715 per night (USD)
Expedia
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 $715 per night (USD)
Expedia

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