Vacation Rentals

Monthly Stays I AMI Waterfront Beach Condo w Pool!
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Watch sunrise over the bay, walk across the street to enjoy the beach. Restaurants & shopping all within walking distance! - Anna Maria Island Vacation Rentals
From $3,800 /Month
Edge of Paradise at Margaritaville - 5 Night Min
South West FL > Anna Maria Island
Condo , Bedroom(s): 3 , Sleeps: 8
Luxe Condo I Resort Amenities I Near Anna Maria Island I Margaritaville - Anna Maria Island Vacation Rentals
From $170 /Night
Gorgeous AMI Villa with private pool & just steps to the beach!
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 3 , Sleeps: 8
Welcome to AMI Villa! When you come to Anna Maria Island, make this charming Mediterranean 3 bed & 3 bath villa with a private pool your home away from home!
From $250 /Night
Cozy Cabana West - Anna Maria Island Vacation Rentals
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 2 , Sleeps: 6
2Bed/2Bath, Private Heated Pool!
From $170 /Night
Blue Turtle Cottage Anna Maria Island  Available for January Dates!
OFFER
Blue Turtle Cottage Anna Maria Island Available for January Dates!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Blue Turtle Cottage Anna Maria Island has a sparkling private pool and is just steps to the white sand beach!
From $299 /Night
Renovated 22 Cottage North End-Steps to Beach Tropical LandscapingHeated Jetted Pool
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 2 , Sleeps: 4
SURF’S UP has been completely and lovingly renovated from top to bottom and is gorgeously decorated!
From $291 /Night
North End Luxury Beach Cottage STEPS TO THE BEACH Heated Pool and Outdoor Living Area
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 2 , Sleeps: 4
Seahorse Cottage is one of our most popular properties located on the desirable North End of Anna Maria with a Heated Pool and Outdoor Living Area
From $291 /Night
Professionally Decorated Pool Home Just Steps To The Beach
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Debby's Place is sure to please! Just 2/10 of a mile from the white sandy beaches and the beautiful waters of Anna Maria Island.
From $240 /Night
Spectacular Location Desirable North End wHeated Pool!
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 6
Moon Shadow South's location can't be beat with peeks of Passage Key in Tampa Bay.
From $243 /Night
SUPER CLEAN-STEPS TO BEACH-WALK TO SHOPS, RESTAURANTS, NIGHT SPOTS - SEE REVIEWS
OFFER
SUPER CLEAN-STEPS TO BEACH-WALK TO SHOPS, RESTAURANTS, NIGHT SPOTS - SEE REVIEWS
South West FL > Anna Maria Island > Bradenton Beach
Townhouse , Bedroom(s): 4 , Sleeps: 10
4 Bdrm, 3 Bath, Private Heated Saltwater Pool, Private Elevator, Sleeps 10! SUPER CLEAN!, STEPS TO BEACH, WALK TO SHOPS/RESTAURANTS/NIGHT SPOTS!
From $2,100 /Week
Island Living, Within Walking Distance To Beach Restaraunts Shops Parks Marina
East Central FL > Vero Beach
House , Bedroom(s): 3 , Sleeps: 6
House, 3 Bedrooms, 2.5 Baths (Sleeps 6)
From $425 /Night
Beautiful Luxury 4 BR2 BA Beach House
OFFER
Beautiful Luxury 4 BR2 BA Beach House
Southeast FL > Pompano Beach
House , Bedroom(s): 4 , Sleeps: 8
Beautiful Luxury 4 BR, 2 BA Beach House in Pompano Beach
From $197 /Night

OFFER 15% discount on any available dates in February 3 night minimum stay

Special offer period: Feb 1, 2021 - Feb 28, 2021

5 Pirates Hideaway Canal Front Home wPrivate Pool and Seawall for your boat
Florida Keys > Lower Keys Area > Little Torch Key
House , Bedroom(s): 3 , Sleeps: 8
House 3 Bed/3 bath (Sleeps 6 adults) This is a 28 day minimum rental
From $200 /Night
Tropical Paradise - Cudjoe Key Rental
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 2 , Sleeps: 6
House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 8)
From $400 /Night
Penthouse Condo in One Particular Harbour Near Anna Maria Island  Marina Access
OFFER
Penthouse Condo in One Particular Harbour Near Anna Maria Island Marina Access
South West FL > Bradenton
Condo , Bedroom(s): 2 , Sleeps: 5
2 BR / 2 BA Penthouse Sleeps 5 - 1.6 Miles from Anna Maria Island Beaches
From $150 /Night
Tropical Florida Oasis Vacation Getaway - Fort Lauderdale Vacation Rental
Southeast FL > Fort Lauderdale
House , Bedroom(s): 3 , Sleeps: 6
Large 3 Bedroom 3 Bath Home in beautiful Coral Ridge - Fort Lauderdale vacation rental
From $295 /Night
Beach Cottage only steps to the white sandy beaches of Anna Maria Island!
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 2 , Sleeps: 6
Beach Basket is a vintage 1920's cottage located on Oak Ave which dead ends to the white sandy beaches and emerald waters of Anna Maria Island!
From $269 /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
Gone Coastal 3 Beautiful Family and Pet Friendly Home
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 6
Welcome to Gone Coastal 3! Luxury three bedroom vacation home located just a short walk from Anna Maria Island’s sugar white sands
From $265 /Night
Serendipity Deux
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
Beach Front New 2020 New Construction
From $1,000 /Night
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!
RUM COVE on Anna Maria Island
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 5 , Sleeps: 14
5 King Bedrooms plus 2 dens and ample outdoor space for all 14 guests allowed. One house from Pine Avenue and one block from the beach.
From $800 /Night
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!
The Bella Siesta: Walking distance to Siesta Village; 5 minutes to Siesta Key Beach
South West FL > Siesta Key
House , Bedroom(s): 3 , Sleeps: 8
Renovated 3 bedroom, 2 bathroom home with new saltwater pool built in 2019.
From $450 /Night
Sand Trap- 4 bedroomheated poolElevator
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
Watch the dolphins play in your backyard...Sweeping views of the ocean, Skyway Bridge, Fort Desoto and Egmont Key Preserve. Heated Pool and Spa
From $800 /Night