Holmes Beach Rentals
From $374 per night (USD)VRBO
Heron Heaven - 3 bedroom private pool home across street from beach - By Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two-story beach house, just a short walk away from Gulf sands, with a rooftop deck and luxurious private pool. A 3 bed t ...
From $374 per night (USD)VRBO
From $466 per night (USD)Expedia
Private Pool - Carefree Cottage by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Colorful and inviting with a vibrant tropical style, Carefree Cottage is a perfectly-named oasis in Holmes Beach where a ...
From $466 per night (USD)Expedia
From $726 per night (USD)VRBO
Starfish Cottage: 1 Block to the Beach! Heated Pool, 4 King Beds by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Starfish Cottage by Anna Maria Life Vacation Rentals 202 64th St, Holmes Beach, FL 34217 What You'll Love About This Ho ...
From $726 per night (USD)VRBO
From $566 per night (USD)Expedia
A Reel Beauty: 2 Blocks to Beach! Pool, Spa, Putting Green, by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Reel Beauty by Anna Maria Life Vacation Rentals 4803 2nd Ave, Holmes Beach, FL 34217 What You'll Love About this Home ...
From $566 per night (USD)Expedia
From $451 per night (USD)VRBO
Beauty & The Beach: 1.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beauty & the Beach by Anna Maria Life Vacation Rentals 205 73rd St, Holmes Beach, FL 34217 What You'll Love About This ...
From $451 per night (USD)VRBO
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North Beach Village 6301 - 3BR/2BA Townhome - Anna Maria Island - By Island Real
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A charming island condo, located in the peaceful North Beach Village community, only a block away from the Gulf of Mexic ...
Click For PricingExpedia
From $225 per night (USD)VRBO
At Ease West: A tropical rental 1/2 block from the beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Location, location, location! What more could you want from a beach house than a gorgeous pool and a half-block stroll t ...
From $225 per night (USD)VRBO
From $384 per night (USD)Expedia
La Coconut: 1 Block to Beach! Dog Friendly! Ping Pong & Foosball, Heated Pool by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
La Coconut by Anna Maria Life Vacation Rentals 3610 Gulf Drive, Holmes Beach, FL 34217 What You'll Love About this Home ...
From $384 per night (USD)Expedia
From $734 per night (USD)VRBO
5 bedroom canal home on AMI, heated pool, pet friendly!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Harborside, a gorgeous canal front home located in Holmes Beach. This is where you’ll want to be for your nex ...
From $734 per night (USD)VRBO
From $717 per night (USD)Expedia
Dilly Dally by the Seas: 1 Block to Beach, Rooftop Deck, Pool & Spa by Anna Maria Life
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Dilly Dally by Anna Maria Life Vacation Rentals 7005 Gulf Dr, Holmes Beach, FL 34217 What You'll Love About This Home: ...
From $717 per night (USD)Expedia
From $348 per night (USD)VRBO
GREAT LOCATION! Peaceful & Tropical Condo Steps to Beautiful Holmes Beach, AMI!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly remodeled! 2 BR and 1.5 BA second-level condo just steps to the white sand and turquoise waters of Holmes Beach on ...
From $348 per night (USD)VRBO
From $424 per night (USD)VRBO
Beautiful House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Close to the Beach with Heated Pool / 3 bedroom plus game area / den Located on the North End of Holmes Beach near Cros ...
From $424 per night (USD)VRBO
From $604 per night (USD)VRBO
Serenity Now - Pet-Friendly Retreat w/ Heated Pool, Near Beach & Tropical Oasis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Serenity Now! On Anna Maria Island (Holmes Beach, FL) A Pet-Friendly Tropical Retreat on Anna Maria Island, ...
From $604 per night (USD)VRBO
From $306 per night (USD)Expedia
Cool Breeze by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
* Important Notice: The HOA has scheduled exterior painting for the condo building from September 22 – October 10, 2025. ...
From $306 per night (USD)Expedia
From $264 per night (USD)VRBO
Martinique 308 South - Condo 2 Bedroom / 2 Bath gulf view , maximum...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Martinique 308 South - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC#20-000122 ...
From $264 per night (USD)VRBO
From $231 per night (USD)Expedia
West Bay Point Moorings 42 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
West Bay Point Moorings 42 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. VRC#20-000124 ...
From $231 per night (USD)Expedia
From $539 per night (USD)VRBO
Hart of the Gulf: Dog Friendly, 2.5 Blocks to Beach, Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hart of the Gulf by Anna Maria Life Vacation Rentals 305 67th St, Holmes Beach, FL 34217 What You'll Love About This Ho ...
From $539 per night (USD)VRBO
From $219 per night (USD)Expedia
West Bay Point Moorings 155 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
West Bay Point Moorings 155 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. VRC#20-000123 ...
From $219 per night (USD)Expedia
From $311 per night (USD)VRBO
Delphina: 2 Bed 2 Bath Water Front Villa Anna Maria Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your classic beach town oasis! AMI is known for its old time feel and elegance. The villa is newly painted ...
From $311 per night (USD)VRBO
From $426 per night (USD)Expedia
Anna Maria Island Direct Beachfront Condo- Awesome View and Amazing Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
View dolphins, terns, gulls, sandpipers, and other shorebirds from your 22 foot wide screened lanai. Walk directly out ...
From $426 per night (USD)Expedia
From $214 per night (USD)VRBO
Terrace Condo 6 Pool Condo Relaxing Tropical Pool Deck Close To Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000268 Are you ready for a relaxing vacation in beautiful Holmes Beach? Look no further than this two-bedroom, tw ...
From $214 per night (USD)VRBO
From $270 per night (USD)Expedia
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 25% discount on the nightly rate! (This discount is ap ...
From $270 per night (USD)Expedia
From $605 per night (USD)VRBO
Chasing Sunsets managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
🌅 Chasing Sunsets by Beach Retreats Vacation Rentals 📍 Holmes Beach | 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Poo ...
From $605 per night (USD)VRBO
From $298 per night (USD)Expedia
Sandy Point Cove 202 - Anna Maria Island -Condo 2 Bedroom/ 2 Bath, maximum...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sandy Point Cove 202 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC16-000538 D ...
From $298 per night (USD)Expedia
From $276 per night (USD)VRBO
TranquiliSea 1: Pet friendly, long term discount, shared resort-style pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 5% discount on the nightly rate. (This discount is app ...
From $276 per night (USD)VRBO
From $259 per night (USD)Expedia
TranquiliSea 2: Pet friendly, long term discount, shared resort-style pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 5% discount on the nightly rate. (This discount is app ...
From $259 per night (USD)Expedia
From $241 per night (USD)VRBO
Canal Front Old Florida Charmer! 2BDRM 2 Full Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Westbay 203 at Westbay Point & Moorings located Bayside in Holmes Beach! Make yourself at home at this Old Fl ...
From $241 per night (USD)VRBO
From $701 per night (USD)Expedia
Miller Time managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxury 4-Bedroom Island Getaway with Pool, and Spa - Just Steps from Holmes Beach! Welcome to your dream vacation home! ...
From $701 per night (USD)Expedia
From $304 per night (USD)VRBO
6250 Holmes North Beach Village - Condo 2 Bedroom /2.5 Bath , maximum...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful Professionally Decorated Villa with community pool, 3 minute walk to beach 6250 Holmes Boulevard ...
From $304 per night (USD)VRBO
From $859 per night (USD)Expedia
Gorgeous 4 bed 4 bath, units C and D
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Duplex C and D are each 2/2 under a shared roof. Units are next to each other and completely updated, tastefully decorat ...
From $859 per night (USD)Expedia
From $805 per night (USD)VRBO
Entire home near the beach with pool and spa access! Great for larger families!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This amazing duplex consists of unit B which is a 2/2 and unit A 2/1. Both units are completely updated with access to ...
From $805 per night (USD)VRBO
From $171 per night (USD)Expedia
Island Duplex unit: 2-bed/2-bath close to beach, pets welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Updated island duplex (Side A only). Our home is just off Gulf Dr and walkable to the beach (3 blocks), Holmes Beach ci ...
From $171 per night (USD)Expedia
From $390 per night (USD)VRBO
Gulf Place Unit 14 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the epitome of coastal luxury at Gulf Place Unit 14, boasting a stunning beach view and pool access just step ...
From $390 per night (USD)VRBO
From $592 per night (USD)Expedia
Large Private Duplex, Heated Pool and Spa, Outdoor Kitchen and TV
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Breezy Beach by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000336 Plan your dream escape to Breezy Beach ...
From $592 per night (USD)Expedia
From $336 per night (USD)VRBO
AMI Home with Private Pool, 5 Minutes to the Beach! - Hawaiian Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Hawaiian Hideaway by Anna Maria Vacations Holmes Beach Private Retreat with Pool VRC16-000298 Welcome to Hawaiian Hid ...
From $336 per night (USD)VRBO
From $625 per night (USD)Expedia
Private Beach Home with Pool, Two Primary Suites, Close to Beach - Coral Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Coral Retreat by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000353 Welcome to Coral Retreat, a vibrant ...
From $625 per night (USD)Expedia
From $499 per night (USD)VRBO
Home with Private Pool, 8 minute walk to Beach! - Villa Portofino
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Villa Portofino by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000358 Villa Portofino is a Mediterranean ...
From $499 per night (USD)VRBO
From $368 per night (USD)Expedia
Home near the beach! Private Pool and Ping Pong Table. - Beachwalk
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beachwalk by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC18-000119 Welcome to Beachwalk, a lovely three-l ...
From $368 per night (USD)Expedia
From $756 per night (USD)VRBO
Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Caribbean Dream by Anna Maria Vacations Private Home in Holmes Beach, FL Embark on an unforgettable retreat at Caribbea ...
From $756 per night (USD)VRBO
From $500 per night (USD)Expedia
Beach Home with Pool, Tiki Bar, and Game Room! Close to Beach - Mango Breeze
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Mango Breeze by Anna Maria Vacations 141 50th Street, Holmes Beach, Florida 34217 VRC17-000130 Welcome to Mango Breeze ...
From $500 per night (USD)Expedia
From $1153 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 Holmes Beach Gulf Front Villa with Rooftop Deck and Pool VRC16-000749 Experi ...
From $1153 per night (USD)VRBO
From $511 per night (USD)Expedia
Private Home with Private Pool and Spa! New Renovations! Close to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Calypso Cottage by Anna Maria Vacations Holmes Beach Beach Retreat with Pool and Tickle Table VRC16-000622 Your islan ...
From $511 per night (USD)Expedia
From $1059 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 Beachfront Family Retreat with Pool and Game Room VRC16-000263 Welcome to Tiki Bea ...
From $1059 per night (USD)VRBO
From $521 per night (USD)Expedia
Home with Private Pool and Spa. Outdoor TV, Grill - Palms By The Bay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Palms By The Bay by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000361 Welcome to Palms By The Bay! Th ...
From $521 per night (USD)Expedia
From $389 per night (USD)VRBO
Elevated Beach Home with Gulf Views! Next to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Starfish by Anna Maria Vacations Holmes Beach Beachside Retreat with Beach Access VRC16-000247 Experience the best of ...
From $389 per night (USD)VRBO
From $325 per night (USD)Expedia
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 206 81st Street Unit B, Holmes Beach, FL 34217 VRC17-000059 Escape to Hawaiia ...
From $325 per night (USD)Expedia
From $608 per night (USD)VRBO
Large Private Beach Home! Heated Pool, Elevator, Balcony, and Near the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Seabreeze Cottage by Anna Maria Vacations Holmes Beach Luxury Beach House with Pool and Elevator VRC16-000366 Enjoy th ...
From $608 per night (USD)VRBO
From $434 per night (USD)Expedia
AMI Home Close to the Beach with Ping Pong, Private Pool and Spa! - Quiet Palms
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Quiet Palms by Anna Maria Vacations Holmes Beach Vacation Home with Pool VRC16-000364 Welcome to Quiet Palms, a tranq ...
From $434 per night (USD)Expedia
From $488 per night (USD)VRBO
Home with Private Pool, Outdoor Bar, Ping Pong, Close to Beach! - Dolphin House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Dolphin House by Anna Maria Vacations 311 64th Street, Holmes Beach, FL 34217 VRC16-000338 Experience the tropical cha ...
From $488 per night (USD)VRBO
From $350 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 117 White Avenue, Holmes Beach, Florida VRC20-000047 Welcome to Away To Play, ...
From $350 per night (USD)Expedia
From $389 per night (USD)VRBO
Renovated Beach Home with Private Pool, Spa and Outdoor Bar! Near Beach! - Pinea
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Pineapple Key by Anna Maria Vacations Holmes Beach Private Beach House with Pool and Tiki Bar VRC16-000364 Welcome to ...
From $389 per night (USD)VRBO
From $495 per night (USD)Expedia
5 Minute Walk to the Beach! Private Heated Pool, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ocean Breeze by Anna Maria Vacations Home in Holmes Beach, FL. 34217 VRC16-000337 Vacation in one of the best Gulf of M ...
From $495 per night (USD)Expedia
From $464 per night (USD)VRBO
Beautiful Home Private Saltwater Pool, Game Room, and Close to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Key Lime Beach House by AMI Locals Holmes Beach Oceanfront Home with Pool & Game Room VRC000324 Welcome to Key Lime B ...
From $464 per night (USD)VRBO
From $600 per night (USD)Expedia
Private Beachfront Condo with Shared Pool & Private Balcony with Beach Views- La
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
LaPlage Unit # 2 by Anna Maria Vacations Condo in Holmes Beach, Fl. 34217 VRC18-000121 Experience the ultimate beachfro ...
From $600 per night (USD)Expedia
From $893 per night (USD)VRBO
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, Fl. 34217 Welcome to Gulfside Oasis! This multi-level ...
From $893 per night (USD)VRBO
From $512 per night (USD)Expedia
Hidden Cove #4! Beachfront Townhouse with Gulf Views and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Hidden Cove #4 by Anna Maria Vacations 5610 Gulf Drive Unit 4, Holmes Beach, FL 34217 VRC16-000044 Welcome to Hidden Co ...
From $512 per night (USD)Expedia
From $527 per night (USD)VRBO
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, 34217 VRC16-000501 Welcome to Sand Dollar! This four bedro ...
From $527 per night (USD)VRBO
From $265 per night (USD)Expedia
Beach Front Duplex with Direct Beach Access and Scenic Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whispering Waves East by Anna Maria Vacations 104 72nd Street Unit B, Holmes Beach, Florida 34217 VRC16-000273 Welcome ...
From $265 per night (USD)Expedia
From $306 per night (USD)VRBO
Oceanfront Duplex with Scenic Beach Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whispering Waves West by Anna Maria Vacations 104 72nd Street Unit A, Holmes Beach, Florida 34217 VRC16-000272 Welcome ...
From $306 per night (USD)VRBO
From $307 per night (USD)Expedia
Beachfront Condo, Pool, Tennis Court, and Private Balcony - Sun Plaza West 110
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sun Plaza West Unit 110 by Anna Maria Vacations Holmes Beach Beachside Condo VRC17-000125 Experience Island life at S ...
From $307 per night (USD)Expedia
From $297 per night (USD)VRBO
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 316B 63rd Street, Holmes Beach, FL 34217 VRC16-000340 Make your vacation dreams co ...
From $297 per night (USD)VRBO
From $500 per night (USD)Expedia
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, FL 34217 VRC16-000304 Welcome to Stay Calm! This ground-l ...
From $500 per night (USD)Expedia
From $351 per night (USD)VRBO
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 Holmes Beach Canalfront Home with Private Dock and Pool VRC16-000743 Welcome ...
From $351 per night (USD)VRBO
From $361 per night (USD)Expedia
Pet-Friendly Home with Private Pool and Ping Pong Table! Short Walk to Beach! -
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Florence by Anna Maria Vacations Holmes Beach Luxury Coastal Home with Pool & Water Access VRC16-000355 Welcome ...
From $361 per night (USD)Expedia
From $268 per night (USD)VRBO
Sunset Villa D by Beach Boutique Rentals
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The ultimate beach vacation awaits you at the Sunset Villas, a cozy 4-unit condo complex with a stunning tropical courty ...
From $268 per night (USD)VRBO
From $415 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 307 59th Street Unit A, Holmes Beach, FL 34217 VRC17-000189 Welcome to Ca ...
From $415 per night (USD)Expedia
From $303 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 4200 Gulf Drive 102 Holmes Beach, FL 34217 VRC16-000363 Welcome to Gulf Sa ...
From $303 per night (USD)VRBO
From $420 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 Holmes Beach Private Pool & Beach Retreat VRC16-000610 Welcome to Egrets Nest, a ...
From $420 per night (USD)Expedia
From $850 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 $850 per night (USD)VRBO
From $347 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 5616 Gulf Drive #106, Holmes Beach, FL 34217 VRC16-000081 Welcome to Gulf ...
From $347 per night (USD)Expedia
From $306 per night (USD)VRBO
Beach Home with Pool and Gas Grill! 2 Minute walk to Beach! - Tiki Sunrise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tiki Sunrise by Anna Maria Vacations Holmes Beach Home with Shared Pool VRC19-000045 Welcome to Tiki Sunrise, a delig ...
From $306 per night (USD)VRBO
From $256 per night (USD)Expedia
Buckeye Haven: Beachfront Community with Tennis Courts!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Buckeye Haven is situated in the sought after community of Playa Encantada. Come enjoy this tropical beach front communi ...
From $256 per night (USD)Expedia
From $464 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 $464 per night (USD)VRBO
From $444 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 $444 per night (USD)VRBO
From $362 per night (USD)VRBO
Community Pool Access, Private Patio with BBQ Grill Near the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunsets and Daydreams by Anna Maria Island Accommodations Home in Holmes Beach, Florida Welcome to Sunsets and Daydr ...
From $362 per night (USD)VRBO
From $277 per night (USD)Expedia
Beach Front 2 bedroom condo on AMI with pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach front resort style condo, staying with us is just another day in Paradise! This spacious unit has two floors, bot ...
From $277 per night (USD)Expedia
From $548 per night (USD)VRBO
5 Minute Short Walk To Beach, Shops and Restaurants - Single Level Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Please see our other property Blue Grotto for Reviews #1974897. Recently renovated with all new kitchens, bathroom and ...
From $548 per night (USD)VRBO
From $414 per night (USD)Expedia
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 $414 per night (USD)Expedia
From $574 per night (USD)VRBO
Villa near the beach with a spacious yard, kitchens, & washer/dryer
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The Surf Shack Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $574 per night (USD)VRBO
From $322 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 $322 per night (USD)Expedia
Click For PricingVRBO
Harrington Bungalow 6 One Block to Gulf Beaches - By Island Real Estate Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Anna Maria Island vacation bungalow that sleeps up to six guests is waiting for you and your family. Ground level vacati ...
Click For PricingVRBO
From $436 per night (USD)Expedia
Newly Remodeled and So Close to the Beach! Turf Yard! Pet Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Honey I'm Holmes by Anna Maria Island Accommodations 305 73rd St Holmes Beach, Florida Welcome to Honey I’m Holmes! Sta ...
From $436 per night (USD)Expedia
From $734 per night (USD)VRBO
Warm, welcoming resort on prime beach area. comfortable and intimate
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Area Information Surrounded by the bustling tourist cities of Tampa, Orlando and Sarasota, you’re just a short drive awa ...
From $734 per night (USD)VRBO
From $478 per night (USD)Expedia
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 $478 per night (USD)Expedia
From $260 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 $260 per night (USD)VRBO
From $296 per night (USD)Expedia
Beautiful Condo on Anna Marie Island at Tiffany Place
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This well appointed condo on Anna Maria is ready for rent! Everything you need is here for you. Pack some clothes and c ...
From $296 per night (USD)Expedia
From $261 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 $261 per night (USD)VRBO
From $400 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 5621 Gulf Dr, Holmes Beach, FL Welcome to Sandpiper Villa, a three bedroom, two bath va ...
From $400 per night (USD)Expedia
From $418 per night (USD)VRBO
Gulf Place Unit 6 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the fun and sun while staying at this beautifully remodeled 3 bedroom, 2 bath Gulf Front condo! Once you enter yo ...
From $418 per night (USD)VRBO
From $374 per night (USD)Expedia
Gorgeous 1 Bed Condo! Beachside with Shared Pool, Near Shops!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts Poolside #115 by Anna Maria Vacations 100 73rd Street, Unit #115, Holmes Beach, FL 34217 VRC16-000672 Welcome ...
From $374 per night (USD)Expedia
From $393 per night (USD)VRBO
Beautiful Beachfront Condo with Pool in Holmes Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts Poolside #102 by Anna Maria Vacations 100 73rd Street, Unit #102, Holmes Beach, FL 34217 VRC21-000173 Welcome ...
From $393 per night (USD)VRBO
From $386 per night (USD)Expedia
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 $386 per night (USD)Expedia
From $387 per night (USD)VRBO
Barefoot Bliss by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Barefoot Bliss, your tranquil escape just two blocks from the pristine shores of Anna Maria Island! *Feature ...
From $387 per night (USD)VRBO
From $317 per night (USD)Expedia
Charming 2Bdrm Coastal Cottage 3 min from Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Southern Cross, your idyllic coastal escape nestled in the heart of Anna Maria Island! This charming cottage ...
From $317 per night (USD)Expedia
From $575 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 $575 per night (USD)VRBO
From $679 per night (USD)Expedia
Island Life at Pineapple Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Bliss! 2BR w/ Pool, Sunny Dining & Open Layout! ✨ Short 2 1/2 block walk to the beach! Relax by the pool, explore ...
From $679 per night (USD)Expedia
From $554 per night (USD)VRBO
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 $554 per night (USD)VRBO
From $403 per night (USD)Expedia
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 $403 per night (USD)Expedia
From $198 per night (USD)VRBO
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 $198 per night (USD)VRBO
From $208 per night (USD)Expedia
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 $208 per night (USD)Expedia