Anna Maria Rentals
From $870 per night (USD)VRBO
Gulf Shore Retreat: Private Pool managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
NO CANCELLATION FEES: Effective for reservations made on or after August 13, 2025) $500 deposit due at time of booking; ...
From $870 per night (USD)VRBO
From $796 per night (USD)Expedia
Casa Mariposa – AMI Luxury Retreat Steps to Beach & Pine Ave w/ Pool & Spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Mariposa! On Anna Maria Island (Anna Maria, FL) Experience Casa Mariposa, Where Coastal Elegance Meets ...
From $796 per night (USD)Expedia
From $1314 per night (USD)VRBO
Batemans – AMI Canal-Front Luxury Home w/ Pool & Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Bateman's! On Anna Maria Island (Anna Maria, FL) Discover Batemans, Where Luxury Meets Waterfront Living On ...
From $1314 per night (USD)VRBO
From $638 per night (USD)Expedia
Ground Floor Luxury Home, very close to Beach, Heated Pool/Spa 🌴🌴🌴🌴
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ground Floor Luxury Home with Heated Pool/Spa, very close to Beach 🌴🌴🌴🌴 Welcome to the AMI Beach Home on beautiful ...
From $638 per night (USD)Expedia
From $307 per night (USD)VRBO
Wake up on the waters of Tampa Bay in a north Anna Maria home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two story elevated beach home with gorgeous water views, steps from park and two fishing piers. Enjoy meals in the separ ...
From $307 per night (USD)VRBO
From $321 per night (USD)Expedia
Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Cabana B by Anna Maria Life Vacation Rentals 301 Poinsettia Rd., Anna Maria, FL 34216 What you'll love about this ...
From $321 per night (USD)Expedia
From $796 per night (USD)VRBO
2-Night Stay Available June 3-5 w/ Private Pool & Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
DESCRIPTION: It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the ...
From $796 per night (USD)VRBO
From $606 per night (USD)Expedia
Toes in the Water: North End, West of Gulf, Steps to Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Toes in the Water by Anna Maria Life Vacation Rentals 110 Palm Ave, Anna Maria, FL 34216 What You'll Love About This Ho ...
From $606 per night (USD)Expedia
From $939 per night (USD)VRBO
Luxury Upscale Beach Home Gulf of Mexico, Private Heated Pool/Spa. Opt. Golfcart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly redesigned elevated pet friendly 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state o ...
From $939 per night (USD)VRBO
From $437 per night (USD)Expedia
Sunkissed by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunkissed is a beautiful, elevated townhome located in Holmes Beach-just a short stroll to the gorgeous white sandy beac ...
From $437 per night (USD)Expedia
From $244 per night (USD)VRBO
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 $244 per night (USD)VRBO
From $308 per night (USD)Expedia
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 $308 per night (USD)Expedia
Click For PricingVRBO
Casa Posada - Cozy 2BR Historic Beach Cottage Steps to Gulf, Pets OK, Hear the Waves!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa Posada! On Anna Maria Island (Anna Maria, FL) Experience the charm of old Florida living with modern co ...
Click For PricingVRBO
From $631 per night (USD)VRBO
Tucked Away in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked Away is a newly renovated custom home with everything you could possibly need for the vacation of a life time. Th ...
From $631 per night (USD)VRBO
From $877 per night (USD)VRBO
Paradise Bound! Backyard Bliss with Sun Shelf, BBQ and Coastal Decor
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Paradise Bound by AMI Locals 205 Sycamore Ave, Anna Maria, FL VR21-000036 Welcome to Paradise Bound, a stunning fou ...
From $877 per night (USD)VRBO
From $623 per night (USD)Expedia
Sea Whisper in north-end Anna Maria with private dock and pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Sea Whisper, our brand new renovated home with 3 bedrooms / 3 bathrooms, private dock, swimming pool, and spa ...
From $623 per night (USD)Expedia
From $312 per night (USD)VRBO
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 $312 per night (USD)VRBO
From $406 per night (USD)Expedia
Weekly Discounts! Exceptional Rating-A Pearl of a Beach Home- private pool & spa
- Bedrooms:
- 2
- 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 $406 per night (USD)Expedia
From $413 per night (USD)VRBO
Charming house with private heated pool, lanai. Great location to beach & shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
What You’ll Love About Sapphire Surf: • Location, Location, Location! Just 2 blocks to the beach, 4 blocks to charming ...
From $413 per night (USD)VRBO
From $643 per night (USD)Expedia
Gulf View Retreat! Pool, Decks and 2 King Beds!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Deckhouse by AMI Locals Anna Maria Island Home with Gulf Views and Private Pool VR20-000007 Welcome to The Deckh ...
From $643 per night (USD)Expedia
From $349 per night (USD)VRBO
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 $349 per night (USD)VRBO
From $348 per night (USD)Expedia
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 $348 per night (USD)Expedia
From $1120 per night (USD)VRBO
Banyan Manor! Canalfront Home with Pool, Spa, Dock and Game Room
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Banyan Manor by Anna Maria Island Accommodations 219 Chilson Ave, Anna Maria, FL 34216 VR20-000064 Welcome to Banya ...
From $1120 per night (USD)VRBO
From $473 per night (USD)Expedia
Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Carefree Cay by Anna Maria Island Accommodations 217 Sycamore Avenue, Anna Maria, FL, 34216 VR16-000412 Welcome to ...
From $473 per night (USD)Expedia
From $562 per night (USD)VRBO
Beautiful home with fenced yard, heated pool, hot tub, and elevator!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Sand Castle by Anna Maria Island Accommodations Holmes Beach, FL 34217 VRC19-000022 Welcome to Sand Castle! Nestled in ...
From $562 per night (USD)VRBO
From $304 per night (USD)Expedia
Bamboo Breeze! Cozy Pool Retreat Near Shops!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bamboo Breeze by Anna Maria Island Accommodations 203 70th Street, Unit B (East Unit), Holmes Beach, Florida VRC16-00 ...
From $304 per night (USD)Expedia
From $449 per night (USD)VRBO
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 $449 per night (USD)VRBO
From $303 per night (USD)Expedia
Home with Private Backyard and Heated Pool - Gulf Breeze Villa B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gulf Breeze Villa B by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC16-000146 Gulf Breeze Vill ...
From $303 per night (USD)Expedia
From $1142 per night (USD)VRBO
Private Luxury Home 1.5 Blocks to Beach! Heated Pool & Hot Tub!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • 1.5 Blocks to the Beach! Access the Sand at the End of Willow Ave! Short Walk! • Private Heated Pool with ...
From $1142 per night (USD)VRBO
From $602 per night (USD)Expedia
Canalfront Home with Pool, Dock and Putting Green! Close to the Beach! - Lavende
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lavender Lagoon by Anna Maria Island Accommodations 123 Crescent Dr, Anna Maria, FL, 34216 VR22-000006 Welcome t ...
From $602 per night (USD)Expedia
From $456 per night (USD)VRBO
Tropical Oasis with Private Pool and Game Room! 3 Blocks to Beach or Bay!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Pelican Place by Anna Maria Island Accommodations Anna Maria Island Family Retreat with Pool & Game Area VR16-000354 W ...
From $456 per night (USD)VRBO
From $991 per night (USD)Expedia
Island Retreat! Pool, Games & Gulf Access!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Pelican Paradise by Anna Maria Island Accommodations Anna Maria Island Luxury Home with Pool, Spa, Elevator, and Game ...
From $991 per night (USD)Expedia
From $299 per night (USD)VRBO
Holmes Beach Vacation Home with Pool, Ping Pong, and Tiki Bar! 6 minutes to Beac
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Banana Cabana by Anna Maria Island Accommodations 318 64th Street, Holmes Beach, Florida 34217 Relax and unwind at Ban ...
From $299 per night (USD)VRBO
From $664 per night (USD)Expedia
Home with Pool and Outdoor Amenities near the Bay and Beach - North End Chic
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
North End Chic by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000361 Welcome to North End Chi ...
From $664 per night (USD)Expedia
From $473 per night (USD)VRBO
Elevated Anna Maria Family Rental with Pool, 1 Block to Beach - Starfish Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Starfish Beach by Anna Maria Island Accommodations Home in Anna Maria, Florida VR16-000393 Welcome to Starfish Beac ...
From $473 per night (USD)VRBO
From $709 per night (USD)Expedia
Canal Front Home with Pool, Spa and Rooftop Deck!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Silver King by Anna Maria Island Accommodations 316 Tarpon St Anna Maria, FL 34216 VR16-000118 Welcome to Silver Ki ...
From $709 per night (USD)Expedia
From $484 per night (USD)VRBO
AMI Escape! 2 King Suites, Twin Room and Private Pool Near Pier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Azure by Anna Maria Island Accommodations 268 Gladiolus St, Anna Maria, FL 34216 VR18-000114 Welcome to Azure, a mo ...
From $484 per night (USD)VRBO
From $304 per night (USD)Expedia
Home with Private Pool and Hot Tub! 3 Blocks to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sand Dollar by Anna Maria Island Accommodations Holmes Beach Private Pool & Hot Tub with Bay and Beach Access VR16-000 ...
From $304 per night (USD)Expedia
From $467 per night (USD)VRBO
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 10-minute walk to the beach • Private pool • Ping pong table • Outdoor shower • Washer an ...
From $467 per night (USD)VRBO
From $533 per night (USD)Expedia
Beautiful Guest House Near the Beach with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 5-minute walk to the beach • Pool Anna Maria Guest House 212 by Anna Marie Accommodations ...
From $533 per night (USD)Expedia
From $502 per night (USD)VRBO
Cozy Pine Ave Cottage Near Beach and Pier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Anna Maria Guest House 317 by Anna Maria Island Accommodations 317 Pine Ave, Anna Maria, FL 34216 Welcome to Anna Mar ...
From $502 per night (USD)VRBO
From $446 per night (USD)Expedia
Beach Cottage! Walk to Dining, Shops and Island Trolley Stop
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beach Cottage by Anna Maria Island Accommodations 211 71st St, Holmes Beach, FL 34217 VRC16-000178 Welcome to Beach ...
From $446 per night (USD)Expedia
From $493 per night (USD)VRBO
Canal Home with Pool & Dock Near Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hammock Dreams by Anna Maria Island Accommodations 131 Hammock Rd, Anna Maria, FL 34216 VR16-000408 Welcome to Hammo ...
From $493 per night (USD)VRBO
From $429 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 $429 per night (USD)Expedia
From $381 per night (USD)VRBO
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 $381 per night (USD)VRBO
From $452 per night (USD)Expedia
Private Home with Pool and Hot Tub, just 5 Houses to the Water!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Baby by Anna Maria Island Accommodations Private home in Anna Maria, Florida 5 Houses to Beach! Highlights: • J ...
From $452 per night (USD)Expedia
From $216 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 308 64th St, Holmes Beach, FL 34217 VRC17-000041 Welcome to Pineap ...
From $216 per night (USD)VRBO
From $642 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 $642 per night (USD)Expedia
From $416 per night (USD)VRBO
Covey Cottage! Walk to Beach, Boutique Shops & City Pier
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Covey Cottage by Anna Maria Vacations 418 Spring Ave, Anna Maria, FL 34216 VR16-000292 Welcome to Covey Cottage, a ...
From $416 per night (USD)VRBO
From $274 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 $274 per night (USD)Expedia
From $462 per night (USD)VRBO
Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Little Pink Houses by Anna Maria Island Accommodations Anna Maria, FL 34216 VR18-000136 Welcome to Little Pink Houses, ...
From $462 per night (USD)VRBO
From $344 per night (USD)Expedia
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 $344 per night (USD)Expedia
From $671 per night (USD)VRBO
Triple Play! Canal, Pool & Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Triple Play by Anna Maria Island Accommodations 313 Iris Street, Anna Maria, Florida VR16-000416 Welcome to Triple ...
From $671 per night (USD)VRBO
From $489 per night (USD)Expedia
AMI Stay! Family-Friendly Home with Pool, Twin Room and Garden Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pink Palm Bungalow by Anna Maria Island Accommodations 304 Palm Ave, Anna Maria, FL 34217 VR16-000353 Welcome to Pi ...
From $489 per night (USD)Expedia
From $714 per night (USD)VRBO
Private Home with Pool and Game Room, 1 Block to Beach! - Dolphin Pointe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dolphin Pointe by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000318 Welcome to Dolphin Poi ...
From $714 per night (USD)VRBO
From $372 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 $372 per night (USD)Expedia
From $716 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 $716 per night (USD)VRBO
From $446 per night (USD)Expedia
Beautiful Condo on Pine Ave, 2 Blocks to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
High Tide Haven by Anna Maria Island Accommodations 306 Pine Ave Anna Maria, FL 34216 Welcome to High Tide Haven where ...
From $446 per night (USD)Expedia
From $477 per night (USD)VRBO
Adorable Cottage with Covered Balconies and Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Social Nest by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 Welcome to Social Nest, a second-level ho ...
From $477 per night (USD)VRBO
From $600 per night (USD)Expedia
Perfect Vacation Home! Pool, Lounge, and Ping Pong
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Cottage by Anna Maria Island Accommodations 310 68th St, Holmes Beach, FL 34217 VRC16-000159 Welcome to Coconu ...
From $600 per night (USD)Expedia
From $625 per night (USD)VRBO
Spacious Canal front Home with Pool, Perfect For Family Vacations!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Gypsy Sol by Anna Maria Island Accommodations 516 Loquat Dr, Anna Maria, FL, 34216 VR18-000034 Welcome to Gypsy So ...
From $625 per night (USD)VRBO
From $692 per night (USD)Expedia
Called in Sic! Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Called in Sic by Anna Maria Island Accommodations 813 Jacaranda Rd, Anna Maria, Florida 34216 VR18-000103 Welcome t ...
From $692 per night (USD)Expedia
From $359 per night (USD)VRBO
Steps to Beach and Pool Cozy Island Flat Near Pine Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 113 B by Anna Maria Island Accommodations 111 Magnolia Ave, Unit B | Anna Maria, FL 34216 VR16-000423 ...
From $359 per night (USD)VRBO
From $1162 per night (USD)Expedia
Luxury Retreat! Pool, Spa & Walk to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Water Colors by Anna Maria Island Accommodations 109 Palm Avenue, Anna Maria, Florida VR18-000060 Welcome to Water ...
From $1162 per night (USD)Expedia
From $176 per night (USD)VRBO
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 $176 per night (USD)VRBO
From $478 per night (USD)Expedia
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 $478 per night (USD)Expedia
From $492 per night (USD)VRBO
Private Home 1 Block to Beach with Pool and Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights • 3-minute walk from Beach • Private pool and hot Tub • Outdoor shower • Washer and dryer Beach You To I ...
From $492 per night (USD)VRBO
From $847 per night (USD)Expedia
Anna Maria Friends Getaway: Private Pool Close to the Beach - Coral Kai
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coral Kai by Anna Maria Island Accommodations Home in Anna Maria, Florida VR20-000067 Welcome to Coral Kai, your ide ...
From $847 per night (USD)Expedia
From $642 per night (USD)VRBO
Island Retreat with Pool and Putting Green
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Lady From the Sea by Anna Maria Island Accommodations 205 Iris St Anna Maria, FL 34216 VR18-000156 Welcome to ...
From $642 per night (USD)VRBO
From $475 per night (USD)Expedia
Private Home with Pool! 1 Block to Beach, Great for Familiy!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Hurricane House by Anna Maria Island Accommodations 205 Spring Ave, Anna Maria, FL, 34216 VR16-000396 Welcome to H ...
From $475 per night (USD)Expedia
From $1040 per night (USD)VRBO
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 $1040 per night (USD)VRBO
From $326 per night (USD)Expedia
Sand & Sea! Relaxing Patio, Shared Pool & Walkable Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 113 A by Anna Maria Island Accommodations 113 Magnolia Ave, Unit A, Anna Maria, FL 34216 VR16-000423 W ...
From $326 per night (USD)Expedia
From $548 per night (USD)VRBO
Casa Allegria: Remodeled Home with Private Pool, Just Over a Block to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Allegria by Anna Maria Island Accommodations 209 Archer Way Anna Maria, FL 34216 VR16-000015 Welcome to Casa Alle ...
From $548 per night (USD)VRBO
From $391 per night (USD)Expedia
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 $391 per night (USD)Expedia
Click For PricingVRBO
Palm Paradise! Pool, Games & Walk to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Palm Paradise by Anna Maria Island Accommodations Anna Maria Vacation Home with Private Pool VR16-000358 Welcome to ...
Click For PricingVRBO
From $334 per night (USD)Expedia
Sand & Sea 109 A! Pool, Patio and Coastal Charm!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 109 A by Anna Maria Island Accommodations 109 Magnolia Ave, Unit A, Anna Maria, FL, 34216 VR16-000422 W ...
From $334 per night (USD)Expedia
From $376 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 $376 per night (USD)VRBO
From $562 per night (USD)Expedia
Canal Home with Private Pool and Dock - North End Zen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
North End Zen by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000360 Recharge your batteries N ...
From $562 per night (USD)Expedia
From $326 per night (USD)VRBO
Beautiful Home Directly Across the Street from the Gorgeous Bay Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shore's Nice by Anna Maria Island Accommodations 912 N Shore Drive, Anna Maria, Florida VR21-000020 Experience your u ...
From $326 per night (USD)VRBO
From $500 per night (USD)Expedia
Private Home Situated Near Bean Point with Spacious Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Absolutely Anna by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000095 Escape to paradise at ...
From $500 per night (USD)Expedia
From $518 per night (USD)VRBO
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 $518 per night (USD)VRBO
From $457 per night (USD)Expedia
Remodeled Duplex with Heated Pool! 2 Blocks to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Turtle Crawl by Anna Maria Island Accommodations 763 Jacaranda Rd, Unit B, Anna Maria, FL, 34216 VR16-000350 Welco ...
From $457 per night (USD)Expedia
From $442 per night (USD)VRBO
Quiet North End Home Only 2 Blocks to Beach with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our Place By The Sea Anna Maria, FL 34216 VR16-000359 Welcome to Our Place By The Sea, an inviting vacation home with a ...
From $442 per night (USD)VRBO
From $358 per night (USD)Expedia
Remodeled Duplex with Heated Pool, 2 Blocks to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Turtle Trax by Anna Maria Island Accommodations 763 Jacaranda Rd, Unit A, Anna Maria, FL, 34216 VR16-000350 Welcom ...
From $358 per night (USD)Expedia
From $323 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 $323 per night (USD)VRBO
From $576 per night (USD)Expedia
Beautiful Home with Pool, Outside Living Area, and Near the Beach! - Coconut Lag
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Coconut Lagoon by Anna Maria Island Accommodations 74 N Shore Dr, Anna Maria, FL, 34216 VR16-000285 Welcome to Coc ...
From $576 per night (USD)Expedia
From $323 per night (USD)VRBO
Quaint Condo with Shared Pool, Only 2 Houses to the Beach - Sand And Sea 109 B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 109 B by Anna Maria Island Accommodations A 109 Magnolia Ave, Unit B, Anna Maria, FL, 34216 VR16-000422 ...
From $323 per night (USD)VRBO
From $361 per night (USD)Expedia
Beachside Retreat with Pool, Patio and Walk to Pine Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 111 B by Anna Maria Island Accommodations 111 Magnolia Ave, Unit B, Anna Maria, FL 34216 VR16-000423 We ...
From $361 per night (USD)Expedia
From $256 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 $256 per night (USD)VRBO
From $485 per night (USD)Expedia
Luxury home near the beach and shopping! Private backyard and pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • 2-minute walk from the beach • Private Pool • Near free Anna Maria Island Trolley stop • Outdoor living spa ...
From $485 per night (USD)Expedia
From $1197 per night (USD)VRBO
Sea La Vie Beach House - Luxury Home w/ Pool, Spa, Dock & Canal Access on Anna Maria
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Sea La Vie Beach House! On Anna Maria Island (Anna Maria, FL) A Luxurious Canal-Front Retreat on Anna Maria ...
From $1197 per night (USD)VRBO
From $479 per night (USD)Expedia
Anna Maria Island, NORTH END 3 bedroom, pet friendly, private pool home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise found in this 3 bedroom, 2 bath pet friendly, home on Anna Maria Island! This family home is just 1 block from ...
From $479 per night (USD)Expedia
From $422 per night (USD)VRBO
Gulf Place Unit 10 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
**ASK ABOUT LAST-MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two-bedroom, two-bath u ...
From $422 per night (USD)VRBO
From $759 per night (USD)Expedia
Bella Vita: Canal front, pool, perfect location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
SECURITY CAMERAS IN USE LIFE IS BEAUTIFUL AND ALWAYS BETTER AT THE BEACH! BELLA VITA. YOUR NEW CORNER OF PARADISE! THI ...
From $759 per night (USD)Expedia
From $1538 per night (USD)VRBO
Once Upon a Tiki: Canal, Dock, Backyard Paradise, Games, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
211 Chilson Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! One Block to the Beach! On a Canal! 5 ...
From $1538 per night (USD)VRBO
From $832 per night (USD)Expedia
Precious Memories: North End! Quick Walk to Beach! Elevator,Pool,Ping Pong & Pool by Anna Maria Life
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Precious Memories by Anna Maria Life Vacation Rentals 753 Jacaranda, Anna Maria, FL 34216 What You'll Love About This H ...
From $832 per night (USD)Expedia
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $424 per night (USD)Expedia
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 $424 per night (USD)Expedia
From $527 per night (USD)VRBO
AMI Breeze! Relaxed Luxury Near the Gulf!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
AMI Breeze by AMI Locals 507 Spring Ave, Anna Maria, FL VR20-000022 Welcome to AMI Breeze! Tucked away in a rela ...
From $527 per night (USD)VRBO
From $359 per night (USD)Expedia
Coconuts 116 - Anna Maria Island - Condo -1 Bedroom/ 1 Bath- maximum...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts 116 - Anna Maria Island - 1 Bedroom/ 1 Bath - maximum occupancy of 6 people. VRC21-000194 Distance to the ...
From $359 per night (USD)Expedia