Holmes Beach Rentals
- From $403 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
205 73rd St, Holmes Beach, FL 34217 What You'll Love About This Home: Location! 1.5 Blocks to the Beach! 2 Bedrooms / ...
From $403 per night (USD)VRBO
- From $513 per night (USD)
Expedia
3 min walk to the beach with large private pool
- 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 $513 per night (USD)Expedia
- From $577 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
202 64th St, Holmes Beach, FL 34217 What You'll Love About This Home: Location! 1 Block to the Beach! 4 Bedrooms / 4 Ba ...
From $577 per night (USD)VRBO
- From $435 per night (USD)
Expedia
GREAT LOCATION! Peaceful & Tropical Condo Steps to Beautiful Holmes Beach, AMI!
- Bedrooms:
- 2
- 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 $435 per night (USD)Expedia
- Click For Pricing
Expedia
The Haven - Family Complex with Pool - Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A The Haven, a dog-friendly duplex, is a combination of 2 halves of 2 ground level units, providing a total of 3 bedroom ...
Click For PricingExpedia
- Click For Pricing
Expedia
Harrington Cottage - New 4BR Private Pool Home - Anna Maria Island - By Island R
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lovely 4 bed, three bath Anna Maria Island beach cottage with private pool, close to the Gulf of Mexico, recently renova ...
Click For PricingExpedia
- From $668 per night (USD)
VRBO
Serenity Now - Newly Listed Holmes Beach Beauty. Heated Pool with Sun Shelf
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Serenity Now! On Anna Maria Island (Holmes Beach, FL) HIGHLIGHTS: - Open layout and spacious Kitchen, Dining ...
From $668 per night (USD)VRBO
- From $178 per night (USD)
Expedia
West Bay Point Moorings 42
- 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#20-000124D ...
From $178 per night (USD)Expedia
- From $356 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:
- 8
305 67th St, Holmes Beach, FL 34217 What You'll Love About This Home: Location! 2.5 Blocks to the Beach! 3 Bedrooms / 2 ...
From $356 per night (USD)VRBO
- From $151 per night (USD)
Expedia
West Bay Point Moorings 155
- 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 $151 per night (USD)Expedia
- Click For Pricing
Expedia
Tiffany Blue- Stunning 2 bedroom condo directly on the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tiffany Blue is a beautiful, beachfront 2 bed/2 bath condo located on historic Anna Maria Island. This comfortable and ...
Click For PricingExpedia
- From $253 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 $253 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Gulf-view condo on Gulf of Mexico-heated pool, tennis and beach access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You will feel like you have arrived at your own private island, a piece of paradise on the Gulf of Mexico. Swim in our ...
From $350 per night (USD)VRBO
- From $209 per night (USD)
Expedia
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 $209 per night (USD)Expedia
- From $280 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 15% discount on the nightly rate. (This discount is ap ...
From $280 per night (USD)VRBO
- From $282 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 15% discount on the nightly rate. (This discount is ap ...
From $282 per night (USD)Expedia
- From $186 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 $186 per night (USD)VRBO
- Click For Pricing
Expedia
2 Bedroom Condo 94520 by Houzlet
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
SEASONAL/SHORT TERM TURNKEY furnished This 2 bedroom, 2 bathroom condo has been fully, and luxuriously, renovated and is ...
Click For PricingExpedia
- From $199 per night (USD)
VRBO
North Beach Village 63
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful Professionally Decorated Villa with community pool, 3 minutes to beach 6250 Holmes Boulevard - North Beach Vil ...
From $199 per night (USD)VRBO
- From $454 per night (USD)
Expedia
Americana AMI Lighthouse - 3BR w\/pool and rooftop deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this unique lighthouse vacation rental w/private pool on Anna Maria Island. The Lighthouse has 3 bedrooms, 2.5 ...
From $454 per night (USD)Expedia
- From $216 per night (USD)
VRBO
La Ola Verde: Pool, 5 Blocks to Beach, 28 Night Min
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
503 71st St, Holmes Beach, FL 34217 What You'll Love About This Home: Location! 5 Blocks to Beach! 3 Bedrooms / 3 Bathr ...
From $216 per night (USD)VRBO
- From $175 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 $175 per night (USD)Expedia
- From $442 per night (USD)
VRBO
GULF BEACH VIEW w\/ Heated Pool, FREE WiFi & Trolley, Great Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Let Gulf Place 14 be your happy place! Walk into this spacious 3-bedroom condo and let the amazing view of the Gulf of M ...
From $442 per night (USD)VRBO
- From $727 per night (USD)
VRBO
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 $727 per night (USD)VRBO
- From $268 per night (USD)
VRBO
Duplex with Private Pool, 4 Minutes to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Hawaiian Hideaway by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000298 Welcome to Hawaiian Hideaway, a t ...
From $268 per night (USD)VRBO
- From $586 per night (USD)
VRBO
Private Beach Home with Private Heated Pool. Two Primary Suites, Close to Beach
- Bedrooms:
- 4
- 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 $586 per night (USD)VRBO
- From $441 per night (USD)
VRBO
Private Pool - Close Walk to the Gulf Beaches!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Villa Portofino by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000358 Villa Portofino is a Mediterranean ...
From $441 per night (USD)VRBO
- From $725 per night (USD)
VRBO
Direct Beachfront Condo convenient walk to shops, restaurants & more.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Rare 4 bedroom Gulf front condo- at the premier condo complex on AMI. La Plage 3 is simply the finest. Come enjoy a rela ...
From $725 per night (USD)VRBO
- From $535 per night (USD)
VRBO
Private Pool with outside dining. Poolside TV and Grill for family fun
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Shore to Please by Anna Maria Vacations Private Home in Holmes Beach, FL Highlights: -Private Heated Pool and Standalon ...
From $535 per night (USD)VRBO
- From $413 per night (USD)
VRBO
Home near the beach! Private Pool and Ping Pong Table. - Beachwalk
- Bedrooms:
- 3
- 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 $413 per night (USD)VRBO
- From $379 per night (USD)
VRBO
Great location in Holmes Beach, close to beach, shopping and restaurants
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Under the Tuscan Sun by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC19 - 000124 Pack your bags for a luxurio ...
From $379 per night (USD)VRBO
- From $943 per night (USD)
VRBO
Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Caribbean Dream by Anna Maria Vacations Private Home in Holmes Beach, FL Embark on an unforgettable retreat at Caribbea ...
From $943 per night (USD)VRBO
- From $591 per night (USD)
VRBO
Comfortable Luxury Home. Recreation Room. Private Pool, Heated Seasonally
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Mango Breeze by Anna Maria Vacations Home in Holmes Beach, Florida 34217 VRC17-000130 Welcome to Mango Breeze, an invit ...
From $591 per night (USD)VRBO
- From $575 per night (USD)
VRBO
Pool, Spa, Games, and Tiki Bar! - View of the Gulf
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
View of the Gulf by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000749 Welcome to View of the Gulf, a mag ...
From $575 per night (USD)VRBO
- From $417 per night (USD)
VRBO
Private Home with large private pool. Pet Friendly! New Renovations!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Calypso Cottage by Anna Maria Vacations Home in Holmes Beach, Fl. 34217 VRC16-000622 Your island vacation awaits at Cal ...
From $417 per night (USD)VRBO
- From $612 per night (USD)
VRBO
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 $612 per night (USD)VRBO
- From $351 per night (USD)
VRBO
Private Beach Home, Steps to the Sand! Beach Gear!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Starfish by Anna Maria Vacations Private Home in Holmes Beach, FL Highlights: -30 second walk to the beach -1796 sq fee ...
From $351 per night (USD)VRBO
- From $440 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 Home in Holmes Beach, Fl 34217 VRC17-000059 Welcome to Hawaiian Tide, a tropical ...
From $440 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Large Private Beach Home. Private Heated Pool, Huge Balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Seabreeze Cottage by Anna Maria Vacations Private Home in Holmes Beach, FL Highlights: -On our Professional Linen Servi ...
From $448 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Marina Sunrise - Beautiful Property! Heated Pool! Short walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Marina Sunrise by Anna Maria Vacations Home in Holmes Beach, FL. 34217 VRC16-000269 Welcome to Marina Sunrise, a beauti ...
From $239 per night (USD)VRBO
- From $1204 per night (USD)
VRBO
Private Beach Home, Easy Walk to the Sand! Private Pool, Game Room
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Room Details Primary Bedroom: King Second Bedroom: King Third Bedroom: King Fourth Bedroom: King Fifth Bedroom: King Si ...
From $1204 per night (USD)VRBO
- From $384 per night (USD)
VRBO
Close to the Beach w\/ Private Pool and Spa! - Quiet Palms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Quiet Palms by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000364 Welcome to Quiet Palms, a peaceful para ...
From $384 per night (USD)VRBO
- From $518 per night (USD)
VRBO
Private Home on AMI. Heated Pool, Outdoor Bar. Easy Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dolphin House – Private Home on Holmes Beach Highlights: -Private Pool, Heated Seasonally (Nov-April) -Poolside Bar wi ...
From $518 per night (USD)VRBO
- From $391 per night (USD)
VRBO
Large Private Beach Home with Private Pool, 1 Minute from Sand! - Away To Play
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Away To Play by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC20-000047 Welcome to Away To Play! Get re ...
From $391 per night (USD)VRBO
- From $417 per night (USD)
VRBO
Elevated Beach Home with Private Heated Pool, Outdoor Bar
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Pineapple Key by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000364 Welcome to Pineapple Key, an inviting ...
From $417 per night (USD)VRBO
- From $210 per night (USD)
VRBO
Pet friendly, close to gulf beaches! 30 seconds away from your toes in the sand!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Starfish Beach Unit 1 -90-second walk to the white sands of the Gulf of Mexico -Large sliding doors to private courtyar ...
From $210 per night (USD)VRBO
- From $413 per night (USD)
VRBO
Entertainment for all! Saltwater Pool, Media Room - Key Lime Beach House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Key Lime Beach House by Anna Maria Vacations Home in Holmes Beach, Fl. 34217 VRC000324 Welcome to Key Lime Beach ...
From $413 per night (USD)VRBO
- From $523 per night (USD)
VRBO
Direct Gulf Condo. Amazing Views. Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Paradise 2 by Anna Maria Vacations Private Condo in Holmes Beach, FL Highlights: -Gulf-Front Condo -Heated Comm ...
From $523 per night (USD)VRBO
- From $894 per night (USD)
VRBO
Complex is Gulf front, steps to the beach and large pool.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in the tropical splendor of this ultra-luxurious beachfront property on Anna Maria Island in a gated community tha ...
From $894 per night (USD)VRBO
- From $511 per night (USD)
VRBO
Private Pool, Game Room, and 1 minute to the beach!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Gulfside Oasis by Anna Maria Vacations Private Home in Holmes Beach, FL Highlights: -On our Professional Linen Service ...
From $511 per night (USD)VRBO
- From $561 per night (USD)
VRBO
Elevated Beach Condo. Multiple Balconies, Direct Beach Views
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Hidden Cove 4 by Anna Maria Vacations Private Condo in Holmes Beach, FL Highlights: -On our Professional Linen Service ...
From $561 per night (USD)VRBO
- Click For Pricing
VRBO
Private Beach Home, Short Walk to the Beach! Private Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Paradise – Private Home in Holmes Beach Highlights: -Private Heated Pool (Heated Seasonally, Nov-April) -5 Minute ...
Click For PricingVRBO
- From $173 per night (USD)
VRBO
Near the beach and shopping with Washer and Dryer, BBQ Grill - Amari Joy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Amari Joy by Anna Maria Vacations Home in Holmes Beach, 34217 VRC22-000228 Welcome to Amari Joy! This two-bedroom, one- ...
From $173 per night (USD)VRBO
- From $341 per night (USD)
VRBO
Old Florida Style! Beachfront Duplex, Steps to the Sand! Quiet Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whispering Waves East by Anna Maria Vacations Home in Holmes Beach, Fl 34217 VRC16-000273 Welcome to Whispering Waves E ...
From $341 per night (USD)VRBO
- From $341 per night (USD)
VRBO
Beachfront Duplex! Close to Dining and Shopping. - Whispering Waves West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whispering Waves West by Anna Maria Vacations Duplex in Holmes Beach, Fl 34217 VRC16-000272 Welcome to Whispering Wa ...
From $341 per night (USD)VRBO
- Click For Pricing
VRBO
Elevated Island Bungalow. Private Heated Pool. 5 Minute Walk to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beach Bliss by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000266 Welcome to Beach Bliss, a quaint, eleva ...
Click For PricingVRBO
- From $255 per night (USD)
VRBO
Beachfront Condo, Private Balcony. Community Pool and Tennis Court
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sun Plaza West Unit 110 – Private Condo in Holmes Beach Highlights: -Beachfront Complex, Partial Beach Views from Cond ...
From $255 per night (USD)VRBO
- From $413 per night (USD)
VRBO
Beach Home in Quiet Neighborhood! Private Pool, Gas Grill, Bikes and More!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sugar Beach – Private Home in Holmes Beach Highlights: -Private Pool, Heated Seasonally (Nov-April) -Bikes, Beach Gear ...
From $413 per night (USD)VRBO
- From $419 per night (USD)
VRBO
Private Beach Home with Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay Calm by Anna Maria Vacations Private Home in Holmes Beach, FL Highlights: -On our Professional Linen Service Prog ...
From $419 per night (USD)VRBO
- From $286 per night (USD)
VRBO
Beautiful Beach Duplex, 1 Minute to the Beach! Community Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Starfish Beach Unit 4 – Private Duplex in Holmes Beach Highlights: -350 Yards to the Beach (1 Minute Walk) -Community ...
From $286 per night (USD)VRBO
- From $446 per night (USD)
VRBO
Canal Front Home with Boat Dock! Easy Walk to the Beach, Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Sandpiper by Anna Maria Vacations Canal front home in Holmes Beach, Fl 34217 VRC16-000743 Welcome to Villa San ...
From $446 per night (USD)VRBO
- From $201 per night (USD)
VRBO
Adorable private house on AMI 2 bedrooms, steps from the sand! Privately owned.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Public beach access 100 steps from your door. Two full bedrooms, washer and dryer, full kitchen and living room. Stand ...
From $201 per night (USD)VRBO
- From $393 per night (USD)
VRBO
Beachside 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 $393 per night (USD)VRBO
- From $303 per night (USD)
Expedia
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 ...
From $303 per night (USD)Expedia
- From $650 per night (USD)
VRBO
Honey I'm Holmes! AMI
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Less than a 5-minute walk from the beach • Private Pool and Hot Tub • Pet Friendly • Outdoor seating and ...
From $650 per night (USD)VRBO
- From $650 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 $650 per night (USD)VRBO
- From $417 per night (USD)
VRBO
Sand Dollar - Private Home on Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This home includes the following features: -Close to the Gulf -Private Pool -BBQ Grill -Private Elevator -Pool Table -Ga ...
From $417 per night (USD)VRBO
- From $390 per night (USD)
VRBO
5-minute walk to the Beach w\/Private Pool and is Pet-Friendly! Villa Florence
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Florence by Anna Maria Vacations Home in Holmes Beach, FL. 34217 VRC16-000355 Welcome to Villa Florence, a magnif ...
From $390 per night (USD)VRBO
- From $275 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 $275 per night (USD)VRBO
- From $362 per night (USD)
VRBO
Home with Private Pool. Short Walk to the Beach - Castway Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Castaway Cottage by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC17-000189 We're thrilled to welcome you to C ...
From $362 per night (USD)VRBO
- From $385 per night (USD)
VRBO
Dream vacation-Direct Gulf Front Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf Sand 102 by Anna Maria Vacations Private Condo in Holmes Beach, FL Enjoy wonderful side views of the Gulf waters a ...
From $385 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Great Private Backyard with Heated Pool, 5 Minute Walk to Beach - Egrets Nest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Egrets Nest by Anna Maria Vacations Home in Holmes Beach, Fl. 34217 VRC16-000610 Welcome to Egrets Nest, a coastal para ...
From $399 per night (USD)VRBO
- From $983 per night (USD)
VRBO
Beautiful Canal front home with excellent views from the roof top deck!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Aqua Bay by Anna Maria Vacations Private Home in Holmes Beach, FL Highlights: -On Our Professional Linen Service Progr ...
From $983 per night (USD)VRBO
- From $798 per night (USD)
Expedia
Beachfront Condo with Balcony! -The Reefs Edge
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Reefs Edge by Anna Maria Vacations Condo in Holmes Beach, FL 34217 VRC16-000345 Welcome to The Reeds Edge, a luxuri ...
From $798 per night (USD)Expedia
- From $391 per night (USD)
VRBO
Sunset Views from This Beach Front Condo.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf Shores 106 is a Gulf front condo located in Holmes Beach on Anna Maria Island. Enjoy beautiful spectacular sunset v ...
From $391 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Vibrant Island Home! Private Pool & Outdoor Dining!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Peacock Way by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000608 Your dream vacation awaits at Peacock W ...
From $263 per night (USD)VRBO
- From $264 per night (USD)
VRBO
Charming Beach Duplex, 1 Minute to the Beach! Heated Pool, Gas Grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tiki Sunrise by Anna Maria Vacations Duplex in Holmes Beach, Fl 34217 VRC19-000045 Welcome to Tiki Sunrise, a beautifu ...
From $264 per night (USD)VRBO
- From $220 per night (USD)
Expedia
Beachfront Community of Playa Encantada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Buckeye Haven is situated in the sought after community of Playa Encantada! Come enjoy this tropical beach front communi ...
From $220 per night (USD)Expedia
- From $571 per night (USD)
VRBO
Hidden Cove (Unit 5) Gulf Front Property on Holmes Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing views from the living room and master bedroom of this 2 bedroom/2.5 bathroom. Take a drink outside and sit on yo ...
From $571 per night (USD)VRBO
- Click For Pricing
Expedia
Sunset Beach 106 - Gulf front, pool and miles of white sandy beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful Sunset Beach Condo directly on the Beach. Superbly decorated with all the blues and greens that the Gulf of Me ...
Click For PricingExpedia
- From $250 per night (USD)
VRBO
Coastal villa near the beach and shopping
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa Riva! A coastal getaway awaits you here at this beautiful 2 bedroom, 2.5 bath condo located in the vibr ...
From $250 per night (USD)VRBO
- From $266 per night (USD)
Expedia
Beach Front condo on Anna Maria Island with pool!
- Bedrooms:
- 3
- 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 $266 per night (USD)Expedia
- Click For Pricing
VRBO
Island Girl West by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Introducing Island Girl West - a remarkable vacation half-duplex that promises an unforgettable Anna Maria Island escape ...
Click For PricingVRBO
- Click For Pricing
VRBO
Island Girl East & West by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Island Girl East & West - a remarkable vacation duplex that promises an unforgettable Anna Maria Island esca ...
Click For PricingVRBO
- From $465 per night (USD)
VRBO
Aquamarine Oasis by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Aquamarine Oasis is an exquisite vacation home located just steps away from the pristine white sands and turquoise water ...
From $465 per night (USD)VRBO
- From $378 per night (USD)
Expedia
Dog-friendly villa near the beach with a spacious yard, kitchens, & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
The Surf Shack Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $378 per night (USD)Expedia
- From $599 per night (USD)
VRBO
Short Walk To Beach, Shops and Restaurants - Single Level Home- New Owners
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
**This property has new owners. Please see our other property Blue Grotto for Reviews #1974897. Also, Vacasa listing #81 ...
From $599 per night (USD)VRBO
- Click For Pricing
VRBO
Resort Sixty-Six Anna Maria Island FL condo unit just steps to the beach.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just steps to the beach, with beautiful sunsets, located on Holmes Beach/Anna Maria Island Florida. Enjoy the comfort of ...
Click For PricingVRBO
- From $364 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 $364 per night (USD)VRBO
- From $660 per night (USD)
Expedia
Beautiful Anna Maria Island! Spacious beautiful house few steps from the beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Mango Mews! What a beautiful and spacious house it is! A relaxing coastal retreat that you have been dreamin ...
From $660 per night (USD)Expedia
- From $219 per night (USD)
VRBO
Paradise - Steps to the Beach
- Bedrooms:
- 2
- 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 $219 per night (USD)VRBO
- From $250 per night (USD)
Expedia
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 $250 per night (USD)Expedia
- From $486 per night (USD)
VRBO
GULF BEACH Directly in Front w\/ Heated Pool, FREE WiFi & Trolley, Great Sunsets!
- 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 ...
From $486 per night (USD)VRBO
- From $140 per night (USD)
Expedia
Fun and updated 1 bedroom condo! Beachfront complex with shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kitchen and Dining area, Living Room, Lanai with direct shared pool access Highlights: -Direct access to the Pool Area ...
From $140 per night (USD)Expedia
- From $215 per night (USD)
VRBO
Newly updated 1 bd poolside condo - perfect for your winter getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kitchen and Dining area, Living Room, Lanai with direct shared pool access Highlights: -Completely updated with all new ...
From $215 per night (USD)VRBO
- From $300 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 $300 per night (USD)Expedia
- From $357 per night (USD)
VRBO
Rennovated Home with Pool Near the Beach! - Casa Tortuga
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Tortuga by AMI Locals Home in Holmes Beach, Florida Don your captain's hat and prepare for an exciting adventure ...
From $357 per night (USD)VRBO
- Click For Pricing
Expedia
Large Rental! Spa, Pool, Tiki Bar, Ocean Views.
- Bedrooms:
- 9
- Bathrooms:
- 10
- Sleeps:
- 24
Large family or group rental. This unique property with 4 suites is great for families or groups. Each suite has its own ...
Click For PricingExpedia
- From $339 per night (USD)
VRBO
Ocean Views - Spacious Unit with Bonus Loft & SwimSpa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Wave From It All - a SkyRun Anna Maria Property Welcome to "A Wave From It All" your perfect retreat on Holmes Bea ...
From $339 per night (USD)VRBO
- From $285 per night (USD)
Expedia
2 Bedrooms with Hot Tub - Steps from Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Castaway Cove - a SkyRun Anna Maria Property Welcome to Castaway Cove, your beach retreat nestled in the heart of An ...
From $285 per night (USD)Expedia