Vacation Rentals

Anna Maria Island Paradise❤️Close to beach, shops&restaurants, heated pool, private lanai!
OFFER
Anna Maria Island Paradise❤️Close to beach, shops&restaurants, heated pool, private lanai!
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Book a relaxing vacation at our condo, situated in a private complex on the beautiful Anna Maria Island, only a short walk to the beach, shops and restaurants!
From $100 /Night

OFFER Last Minute Deal - Christmas week- December 19-26 $1,100 per week plus taxes and fees!

Special offer period: Dec 19, 2020 - Dec 26, 2020

Two Blocks from the Beach ~ The Pink Chicken!
OFFER
Two Blocks from the Beach ~ The Pink Chicken!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Special DISCOUNTED Fall Rates! ~ Welcome to the Pink Chicken! A beautifully updated and bright 3 bedroom home on Anna Maria Island
From $150 /Night
Tropical Setting and Heated Lagoon Style Pool at "Your Own Oasis"
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Your Own Oasis is a newer, 3bed/2bath Retreat with a Private Lagoon Style Pool, close to both Bay and Beach and the free trolley stop is just one block away!
From $157 /Night
Beach House Ultimate Pool Family Vacation Home
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
3 bedroom, 2 bathroom ,private heated pool, 5 minute walk to the beach. We have an outside shower for your convenience
From $1,100 /Week
Beautiful Classy Gulf Coast Anna Maria Island, Private Pool, Close to Beach
South West FL > Anna Maria Island > Holmes Beach
Bungalow , Bedroom(s): 3 , Sleeps: 6
3 bedroom, 2 bath duplex bungalow with its own private backyard and pool. Beautifully decorated, 3 minute walk to beach, walk to restaurants, marina, shops.
From $167 /Night
Chic on the Beach
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 4 , Sleeps: 8
side A 2 bedroom, den. 2.5 bath. 1 king, 1 queen, daybed in den. 4 smart TVs,Spa pool Side B 2 king bedroom, den. 2.5 bath. 4 smart TVs spa pool
From $2,000 /Week
Gone Coastal Too: Beautiful Family & Pet-Friendly Private Home
OFFER
Gone Coastal Too: Beautiful Family & Pet-Friendly Private Home
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 2 , Sleeps: 4
Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area!
From $165 /Night

OFFER Special DISCOUNTED Fall Rates

Special offer period: Sep 26, 2020 - Dec 18, 2020

Sandy Isle Getaway - Anna Maria Island
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Condo, 2 Bedrooms, 2 Baths, 6 Sleeps
Anna Maria Island - Beach View Condo
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Large 2 bed/2 bath condo in a great location just steps from the beach. No roads to cross to get to the beach make this a great location for families.
From $140 /Night
Gone Coastal: Beautiful Pet-Friendly Home w Heated Saltwater Pool
OFFER
Gone Coastal: Beautiful Pet-Friendly Home w Heated Saltwater Pool
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 2 , Sleeps: 4
Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area!
From $165 /Night

OFFER Book Now and save 15% off fall rates!

Special offer period: Sep 26, 2020 - Dec 18, 2020

Songbird Cottage B
South West FL > Anna Maria Island > Holmes Beach
Cottage , Bedroom(s): 2 , Sleeps: 5
We live here part time and it is loved and well cared for. And I'm pretty confident that you can't beat it at this price range.
From $85 /Night
BRAND NEW ISLAND HOME w Pool & Spa, 1 Block to Beach & Shops
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 4 , Sleeps: 8
Gorgeous BRAND NEW BUILD 4-5 Bed 4 Bath w/Heated Pool & Spa, 1 Block to Beach
BRAND NEW GORGEOUS ISLAND HOME! 3 Bedroom Block to Beach w Pool
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
BRAND NEW CONSTRUCTION 3 Bedroom, 2 Bath Single Family Home with Heated Pool
From $300 /Night
Palm Perch...the perfect island getaway!
South West FL > Anna Maria Island > Holmes Beach
Apartment , Bedroom(s): 2 , Sleeps: 4
Palm Perch... Newly renovated unit close to beach, shopping & restaurants
From $225 /Night
Club Bamboo South Suite 120
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 1 , Sleeps: 4
Gulf front studio condo with panoramic ocean view directly on the beach. Maximum occupancy is 4 people. It has a King size bed and pullout love seat/ottoman.
From $105 /Night
Gulf Dr location - 700 ft to Beach, Lg heated pool, Gas grill, New decor & renovations
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 3 , Sleeps: 7
Whispering Palms Villa is 1350 sq. ft. 3 bed/2 bath, private outdoor shower off getaway BONUS room. Large open deck plus Large screened Lanai! Private parking!
From $210 /Night
Beachwalk Bungalow
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 8
3 Br, 2 Ba Home Located on North end of Anna Maria, Less than 140 steps to Bean Point
From $150 /Night
Coral Castle - Waterfront! 3 Min Walk To Beach!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 5 , Sleeps: 10
5 bedrooms, 3.5 baths, Sleeps 10
From $1,995 /Week
Sandy Pointe 110 Blocks from the beach, Trolley nearby
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 5
Sandy Pointe 110 Blocks from the beach, Trolley nearby
From $125 /Night
Salty Dogs  Beach House on Anna Maria Island
OFFER
Salty Dogs Beach House on Anna Maria Island
Central West FL
House , Bedroom(s): 3 , Sleeps: 6
Salty Dogs on Anna Maria Island is the perfect location for your family vacation. Amenities include private pool and spa, elevator and we are pet friendly.
From $349 /Night

OFFER Special Fall Rates October 24 through December 12, 2020

Special offer period: Oct 24, 2020 - Dec 12, 2020

LaPlage 9 - Gorgeous Luxury Beachfront Condo Rental on Anna Maria Island
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 3 , Sleeps: 6
3 bedrooms and 2.5 bathrooms in Holmes Beach, FL Walk out of the backyard and hit the beach in this luxury beachfront condo rental on Anna Maria Island, Florida
Conch Out Beach House! 4 bed 3 bath HUGE yard, heated pool & spa, gazebo
South West FL > Anna Maria Island > Holmes Beach
Bungalow , Bedroom(s): 4 , Sleeps: 10
BOOK WITH CONFIDENCE 100% REFUNDABLE IF CANCELED AT LEAST 48 HOURS BEFORE ARRIVAL Visit our direct website for pricing and more photos: www.BeachRetreatsFL.com
From $399 /Night
Island Garden Villas ~ a Tropical Oasis of 1 and 2 bedroom private cottages close to beach
South West FL > Anna Maria Island > Holmes Beach
Cottage , Bedroom(s): 2 , Sleeps: 6
Island Garden Villas offers a total of six 1 and 2 bedroom private cottages ~ So close to beach and pet friendly!
Style of the Isle -walking distance to white beaches on Anna Maria Island
OFFER
Style of the Isle -walking distance to white beaches on Anna Maria Island
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 4
lovely 2 bed /2 bath condo, within walking distance to the beach located in Holmes Beach, Anna Maria Island, within close proxitmity to beach, Publix,pool, WiFi
From $95 /Night
307 65th St Brand new 5 bed, 4 bath island beauty Heated pool & spa, free WiFi, sleeps 12
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 5 , Sleeps: 10
BOOK WITH CONFIDENCE ALL NEW RESERVATIONS ARE 100% REFUNDABLE IF CANCELED AT LEAST 48 HOURS BEFORE ARRIVAL For pricing and more photos: www.BeachRetreatsFL.com
From $399 /Night