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Vacation Rentals

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Gorgeous AMI Villa with private pool & just steps to the beach!
From $225 /Night
Villa
Anna Maria Island > Holmes Beach
Penthouse Condo in One Particular Harbour Near Anna Maria Island Marina Access
From $150 /Night
Condo
South West FL > Bradenton
Historic Gem in the heart of Jupiter Florida
From $3,100 /Month
House
Southeast FL > Jupiter
Beachfront -Direct ocean view - Apollo 306
From $119 /Night
Condo
South West FL > Marco Island
Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
From $480 /Night
House
Anna Maria Island > Anna Maria
Beachfront condo on Siesta Key
From $1,195 /Week
Condo
South West FL > Siesta Key
Edge of Paradise at Margaritaville - 5 Night Min - monthly's wanted
From $170 /Night
Condo
South West FL > Anna Maria Island
4BR-Updated Town home- 360 tour- WALK to PoolLazy River FREE WIFI ~~Near Disney
From $89 /Night
Townhouse
Central FL, Orlando Area, Disney > Davenport
*Luxury Executive Villa ~ Sunset Lakes ~ Just 5 Minutes From Disney's Animal Kingdom*
From $261 /Night
Villa
Central FL, Orlando Area, Disney > Kissimmee
Absolute Anna Maria
From $131 /Night
Condo
South West FL > Anna Maria Island
Meehan - sleeps 6 with heated pool, downtown Port Charlotte from $112nt
From $112 /Night
House
South West FL > Port Charlotte
Beautiful Park Shore Beach on the Gulf of Mexico
From $8,000 /Month
Condo
South West FL > Naples
GORGEOUS 8TH FL. RESORT CONDO MONTHLY STAYS - GULF OF MEXICO VIEWS IN MOST ROOMS
From $6,000 /Month
Condo
South West FL > Naples
Oceanfront Luxury - Amelia Island Florida Beachfront Condo Rental
From $349 /Night
Condo
Northeast FL > Amelia Island
AMI Waterfront Bradenton Beach Condo w Pool!
From $890 /Week
Condo
Anna Maria Island > Bradenton Beach
Anna Belle - Waterfront Luxury Home: North End wDock, Pool, Spa, Screened Lanai, Free WiFi
From $300 /Night
House
Anna Maria Island > Anna Maria
CCVS - The Villa Starfish Lake is located on the same lake 'Starfish Lake' in Cape Coral
From $121 /Night
House
South West FL > Cape Coral
Anna Maria Island Paradise❤️Close to beach, shops&restaurants, heated pool, private lanai!
From $100 /Night
Condo
Anna Maria Island > Holmes Beach
Beautiful, Gulf-Front Home --Halcyon House
From $750 /Night
House
Anna Maria Island > Anna Maria
Luxurious Islamorada ,Private Sandy Beach Access. Hammocks, Kayaks, & More!
From $486 /Night
House
Islamorada Area > Islamorada
Sandy's Siesta Key Condo
From $140 /Night
Condo
South West FL > Siesta Key
❤️ Cozy Haven Minutes to Disney ❤️ Resort Amenities ❤️
From $175 /Night
House
Central FL, Orlando Area, Disney > Kissimmee
❤️ Enjoy Relaxing with Peaceful Lake Views ❤️
From $175 /Night
House
Central FL, Orlando Area, Disney > Kissimmee
Cozy Cabana West
From $170 /Night
Villa
Anna Maria Island > Holmes Beach
❤️ Upscale Comfort with Private Pool & Hot Tub ❤️
From $350 /Night
House
Central FL, Orlando Area, Disney > Kissimmee
Sirenia Cove - Htd Pool Waterfront Dock Ping Pong Outdoor Bar Backyard Beach
From $1,799 /Week
House
Anna Maria Island > Anna Maria
Oct 3 - Oct 10 Deal! - Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
From $233 /Night
House
Anna Maria Island > Anna Maria
Sirenia By The Sea - Waterfront Pool Hot Tub Dock Sauna - Steps to the Beach
From $1,999 /Week
House
Anna Maria Island > Anna Maria
Blue Turtle Cottage Anna Maria Island Available For Christmas & New Years!
From $256 /Night
House
Anna Maria Island > Holmes Beach
Absolute Anna Maria
Absolute Anna Maria
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
WELCOME TO OUR FAMILY FRIENDLY CONDOMINIUM
ID#: 1763
From $131 /Night

0 Reviews
Gorgeous AMI Villa with private pool & just steps to the beach!
OFFER
Gorgeous AMI Villa with private pool & just steps to the beach!
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 3 , Sleeps: 6
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!
ID#: 2114
From $225 /Night

0 Reviews

OFFER Last Minute Deal-$2,160 per week ALL IN (including all taxes and fees!)

Special offer period: Oct 31, 2020 - Nov 21, 2020

Anna Belle - Waterfront Luxury Home: North End wDock, Pool, Spa, Screened Lanai, Free WiFi
OFFER
Anna Belle - Waterfront Luxury Home: North End wDock, Pool, Spa, Screened Lanai, Free WiFi
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 8
Ground level living, 3 bedrooms, 2 baths, sleeps 8. Private Home with Waterfront Dock, Pool, Hot Tub, Wifi
ID#: 1228
From $300 /Night

20 Reviews

OFFER November Escape - $300/per Night, 4 Night Minimum

Special offer period: Nov 7, 2020 - Nov 21, 2020

Edge of Paradise at Margaritaville - 5 Night Min - monthly's wanted
Edge of Paradise at Margaritaville - 5 Night Min - monthly's wanted
South West FL > Anna Maria Island
Condo , Bedroom(s): 3 , Sleeps: 8
Luxe Condo I Resort Amenities I Near Anna Maria Island I Margaritaville
ID#: 2015
From $170 /Night

5 Reviews
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!
ID#: 857
From $100 /Night

13 Reviews

OFFER Last Minute Deal - $1,105 per week ALL IN (including all taxes and fees!)

Special offer period: Oct 24, 2020 - Nov 28, 2020

Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
The Blue Heron is a beautiful 4 bedroom 3.5 bath brand new luxury home on Anna Maria Island for rent.
ID#: 2057
From $480 /Night

4 Reviews
Sirenia By The Sea - Waterfront Pool Hot Tub Dock Sauna - Steps to the Beach
Sirenia By The Sea - Waterfront Pool Hot Tub Dock Sauna - Steps to the Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 5 , Sleeps: 12
Picture yourself vacationing in a huge 5 Bedroom luxurious tropical villa, the perfect vacation rental for large groups on beautiful Anna Maria Island.
ID#: 2
From $1,999 /Week

40 Reviews
Sirenia Cove - Htd Pool Waterfront Dock Ping Pong Outdoor Bar Backyard Beach
Sirenia Cove - Htd Pool Waterfront Dock Ping Pong Outdoor Bar Backyard Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 10
Sirenia Cove is the perfect vacation home to nature lovers. Located directly on the waterfront, you are perched on a prime location to enjoy everything.
ID#: 5
From $1,799 /Week

44 Reviews
Oct 3 - Oct 10 Deal! - Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
Oct 3 - Oct 10 Deal! - Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 10
Sirenia Beach House ~ Beach Resort Style Luxury - Waterfront - Dock - Htd Pool - Spa - Backyard Beach - Tiki Hut - Hammock and more!
ID#: 4
From $233 /Night

63 Reviews
Blue Turtle Cottage Anna Maria Island Available For Christmas & New Years!
Blue Turtle Cottage Anna Maria Island Available For Christmas & New Years!
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!
ID#: 3
From $256 /Night

46 Reviews
Beautiful, Gulf-Front Home --Halcyon House
Beautiful, Gulf-Front Home --Halcyon House
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
As seen in Coastal Living Magazine, this is a 3 bedroom beachfront home on desirable Bean Point with with direct access to Bean Point Beach.
ID#: 532
From $750 /Night

6 Reviews
Anna Maria Island Retreat
Anna Maria Island Retreat
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
ID#: 1775
From $153 /Night

0 Reviews
Bay Watch Bungalow
Bay Watch Bungalow
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
Bay Watch Bungalow: Water Views from Every Room & Upgrades Galore
ID#: 1778
From $118 /Night

0 Reviews
The Anna Maria Island Beach Sands 203
The Anna Maria Island Beach Sands 203
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
The Anna Maria Island Beach Retreat, 2 bedrooms, 1 bathroom, sleeps 6 maximum
ID#: 1773
From $152 /Night

0 Reviews
22 North End Beach House near Bean Point Beach!!
22 North End Beach House near Bean Point Beach!!
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 2 , Sleeps: 4
Located on the desirable North end of Anna Maria Island just steps away from the famous Bean Point Beach, Rod N Reel Pier and Bayfront Park!
ID#: 2065
From $269 /Night

10 Reviews
PRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL
PRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 4
LUXURY CONDO 2 Bed 2 Bath * SEE SUNSET FROM LANAI * WALK TO SHOPS/RESTAURANTS
ID#: 920
From $171 /Night

63 Reviews
One-of-a-Kind 33 Luxury Beach House on the desirable North End of Anna Maria!
One-of-a-Kind 33 Luxury Beach House on the desirable North End of Anna Maria!
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 6
Come relax and enjoy this stunning retreat with a modern, clean beach style ambiance. The white sandy beaches of Bean Point are only a 5 minute stroll away!
ID#: 2063
From $448 /Night

10 Reviews
Tropical Setting and Heated Lagoon Style Pool at "Your Own Oasis"
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!
ID#: 914
From $157 /Night

1 Reviews
North End Luxury Beach Cottage STEPS TO THE BEACH Heated Pool and Outdoor Living Area
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
ID#: 2064
From $291 /Night

10 Reviews
The Anna Maria Island Beach Castle
The Anna Maria Island Beach Castle
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
ID#: 1766
From $152 /Night

0 Reviews
The Anna Maria Island Beach Castaway 1
The Anna Maria Island Beach Castaway 1
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
ID#: 1770
From $101 /Night

0 Reviews
The Anna Maria Island Beach View 208
The Anna Maria Island Beach View 208
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 4
FAMILY/CHILD FRIENDLY CONDOMINIUM!!!
ID#: 1777
From $131 /Night

0 Reviews
Renovated 22 Cottage North End-Steps to Beach Tropical LandscapingHeated Jetted Pool
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!
ID#: 2062
From $291 /Night

11 Reviews
Spectacular Location Desirable North End wHeated Pool!
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.
ID#: 913
From $243 /Night

16 Reviews
Boaters Delight Canal Front Home - with Private Dock - Pool and Spa
Boaters Delight Canal Front Home - with Private Dock - Pool and Spa
South West FL > Bradenton
House , Bedroom(s): 3 , Sleeps: 6
Great Canal Front Views, Huge Screened in Pool and Spa, Private Boat Dock and Only 3 miles to Anna Maria Island Beaches!!
ID#: 1145
From $160 /Night

7 Reviews
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