Vacation Rentals

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 $700 /Week
Sunkissed & Salty: Dreamy Amenities. Prime Location. Available Beginning May 15, 2021
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
New Anna Maria Vacation Rental Home Completing 5/2/2021 4 Bed; 4 Bath, Pool & Spa, Putting Green, Cornhole, Game-room. 1.5 minutes walk to beach. Gulf Views
From $525 /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
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 $229 /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 $286 /Night
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 $160 /Night
Starfish Isle 4 Bedroom3 Bath ~ Private HEATED Pool & Spa, Close to BEACH! Free WiFi
South West FL > Anna Maria Island > Holmes Beach
Townhouse , Bedroom(s): 4 , Sleeps: 4
BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF CANCELED AT LEAST 14 DAYS BEFORE ARRIVAL
From $275 /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
Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 4 , Sleeps: 8
4 bedrooms, 3.5 baths, max. 8 guests, max. 4 vehicles
From $2,100 /Week
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
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
Beach front Luxury condo gulf views and gated parking
South West FL > Anna Maria Island > Anna Maria
Condo , Bedroom(s): 3 , Sleeps: 6
Stunning 3 bedroom beach front Condo. Only steps from the beach, enjoy unbelievable sunsets every evening from the large gulf facing balcony.
From $499 /Night
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
Manatee Watch - Waterfront! 3 Min Walk To Beach!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
3 bedrooms, 2 baths, Sleeps 6
From $2,800 /Week
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, max. 10 guests, max. 5 vehicles
From $2,975 /Week
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
Angel Sea
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 6 , Sleeps: 12
2 BLOCKS TO BEACH, HEATED POOL, HOT TUB HIGH-SPEED WIFI
From $399 /Night
Beach Bliss
South West FL > Anna Maria Island > Holmes Beach
Townhouse , Bedroom(s): 3 , Sleeps: 6
This beautiful 3 bedroom 3 bathroom bungalow. Huge heated pool and spa and beach gear and t.v's in every bedroom.
From $225 /Night
La Casa Costiera 12 - Fabulous Beachfront Condo 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 Sink your toes in the sand just steps away from this luxury condo unit with a heated pool
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!
Westbay Point and Moorings-Dancing Dolphin
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 4
2BD/2BA Condo in Holmes Beach, FLorida
From $3,000 /Month
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 $250 /Night
Two Blocks from the Beach ~ The Pink Chicken!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Welcome to the Pink Chicken! A beautifully updated and bright 3 bedroom home on Anna Maria Island!
West Bay Point and Moorings Condo with Prime Deck Views of AMI Sound! jan thru march deal
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 4
Recent review: "We rented this condo for an entire winter, can wholeheartedly recommend it. well-furnished condo, deck overlooking Bimini Bay. one of the best!"
From $130 /Night

OFFER 10% discount for Jan through March rentals!!

Special offer period: Jan 1, 2022 - Mar 31, 2022