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Vacation Rentals

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Book Starting Aug15 New Home New Resort, Free Pool Heat, 5Min Walk to Lazy River
From $290 /Night
House
Central FL, Orlando Area, Disney > Davenport
551-Luxury Villa Private Pool-Hot Tub-Game Room
From $399 /Night
Villa
Central FL, Orlando Area, Disney > Kissimmee
Sunset Paradise
From $338 /Night
House
Lower Keys Area > Summerland Key
LOCATION SIESTA & DT SARASOTA Coastal Elegant House West of the Trail Family Fun
From $245 /Night
House
South West FL > Sarasota
OneMoreDay
From $3,100 /Week
House
Marathon Area > Key Colony Beach
Direct Gulf Front Condo
From $200 /Night
Condo
Anna Maria Island > Bradenton Beach
WorkStudy from "home" while on vacation. 1 Bedroom
From $886 /Week
Villa
Anna Maria Island > Holmes Beach
Vintage Florida Cottage 450 steps to the beach!
From $150 /Night
Cottage
Anna Maria Island > Bradenton Beach
Wonderful Home in Sarasota Bay on Salt Water Canal in Longboat Key
From $2,198 /Week
House
South West FL > Longboat Key
Seaduction - New Decor Coming May 18th!!
From $1,450 /Week
Condo
Anna Maria Island > Holmes Beach
Beautiful Three Bedroom Townhome Anna Maria Island - Monthly Stays
Townhouse
Anna Maria Island > Holmes Beach
NEW LISTING - Gulf Access Home with Heated Pool & Large Lanai
From $135 /Night
House
South West FL > Cape Coral
Villa Costa - Cape Coral Vacation Rental with Dock
From $109 /Night
House
South West FL > Cape Coral
East Lake Gem on the Green
From $259 /Night
House
Central West FL > Palm Harbor
Marco Island 17th Floor Beachfront Condo with AMAZING Views
From $225 /Night
Condo
South West FL > Marco Island
A Gardeners Cottage Home Becomes Your Sanctuary
From $60 /Night
Cottage
Central FL, Orlando Area, Disney > Maitland
Charming Beachy - Bohemian Cottage in Historic Lake Worth Beach Area
From $275 /Night
House
Southeast FL > Lake Worth Beach
New Listing - May Special - Oceanside Luxury Home in St. Augustine
From $2,500 /Week
House
Northeast FL > Saint Augustine Beach
The Veranda on Jacaranda - Luxury Home, North Anna Maria Island across from Bean Point
From $350 /Night
House
Anna Maria Island > Anna Maria
Sorrento Vacation Rental in Naples- Vanderbilt Beach
From $580 /Night
House
South West FL > Naples
SMUGGLER'S COVE RESORT - Anna Maria Island Vacation Rentals
From $130 /Night
Condo
Anna Maria Island > Bradenton Beach
White Sands Resort - Weekly - Naples vacation rentals
From $129 /Night
Condo
South West FL > Naples
Villa Sanibel Shell in Cape Coral
From $253 /Night
Villa
South West FL > Cape Coral
Gorgeous AMI Villa with private pool & just steps to the beach!
From $300 /Night
Villa
Anna Maria Island > Holmes Beach
Beachfront -Direct ocean view - Apollo 306
From $275 /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
Fantastic 4 BR Villa with private Courtyard Pool, south facing
From $100 /Night
Villa
Central FL, Orlando Area, Disney > Haines City
Edge of Paradise at Margaritaville - 5 Night Min
From $170 /Night
Condo
South West FL > Anna Maria Island
Brand New Luxury Rental 5Bdr 4.5Bath Solterra Resort - Pool, Tennis, Near Disney
House
Central FL, Orlando Area, Disney > Davenport
Affordable Rates on Anna Maria Island!
Affordable Rates on Anna Maria Island!
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 4
Beautiful Condo on Anna Maria Island!
ID#: 1345
From $99 /Night

3 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
Anna Maria Island Paradise❤️Close to beach, shops&restaurants, heated pool, private lanai!
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 $700 /Week

13 Reviews
Edge of Paradise at Margaritaville - 5 Night Min
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
ID#: 2015
From $170 /Night

13 Reviews
Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
OFFER
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 - Anna Maria Island Vacation Rentals
ID#: 2057
From $480 /Night

12 Reviews
Sunkissed & Salty: Dreamy Amenities. Prime Location. Steps to Beach
Sunkissed & Salty: Dreamy Amenities. Prime Location. Steps to Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
New 4 Bed; 4 Bath, Pool & Spa, Putting Green, Cornhole, Game-room and more! 1.5 minute walk to beach. Limited Gulf view
ID#: 103
From $530 /Night

1 Reviews
The Veranda on Jacaranda - Luxury Home, North Anna Maria Island across from Bean Point
The Veranda on Jacaranda - Luxury Home, North Anna Maria Island across from Bean Point
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 8
Newer 3 story Home and beautifully decorated. Elevator to access all floors. Garage parking, private fenced yard, heated pool, beach gear, 6 Bikes, Ocean views.
ID#: 2185
From $350 /Night

0 Reviews
REDUCED MAY PRICES!
OFFER
REDUCED MAY PRICES!
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 in a tropical backyard and is just steps (Less than 100!) to the white sand beach!
ID#: 3
From $250 /Night

46 Reviews

OFFER May Prices Reduced!

Special offer period: Apr 30, 2021 - Jun 27, 2021

Anna Belle - Waterfront Luxury Home: North End wDock, Pool, Spa, Screened Lanai, Free WiFi
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 - Anna Maria Island Vacation Rentals
ID#: 1228
From $700 /Night

20 Reviews
Sirenia Beach House Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
Sirenia Beach House 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 $1,799 /Week

63 Reviews
Gorgeous AMI Villa with private pool & just steps to the beach!
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!
ID#: 2114
From $300 /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 Anna Maria Vacation Rental for large groups
ID#: 2
From $1,999 /Week

40 Reviews
SMUGGLER'S COVE RESORT - Anna Maria Island Vacation Rentals
SMUGGLER'S COVE RESORT - Anna Maria Island Vacation Rentals
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 1 , Sleeps: 4
Quiet family friendly resort with access to the Bay and the Gulf
ID#: 2149
From $130 /Night

0 Reviews
AMI Waterfront Beach Condo w Pool!
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
ID#: 1321
From $1,250 /Week

22 Reviews
Seaduction - New Decor Coming May 18th!!
Seaduction - New Decor Coming May 18th!!
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
2 Bed, 2 Bath Condo on Holmes Beach - 400 steps to the beach
ID#: 2222
From $1,450 /Week

0 Reviews
Vintage Florida Cottage 450 steps to the beach!
Vintage Florida Cottage 450 steps to the beach!
South West FL > Anna Maria Island > Bradenton Beach
Cottage , Bedroom(s): 2 , Sleeps: 4
450 Steps to the beach!
ID#: 2224
From $150 /Night

0 Reviews
WorkStudy from "home" while on vacation. 1 Bedroom
WorkStudy from "home" while on vacation. 1 Bedroom
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 1 , Sleeps: 4
This one bedroom unit has a large office space in addition to the living area and is just across the street from famous Manatee Beach.
ID#: 2225
From $886 /Week

10 Reviews
Live Your Dreams Today
OFFER
Live Your Dreams Today
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Enjoy sunsets from your private balcony overlooking the Gulf of Mexico’s sandy beaches. Your perfect piece of paradise awaits in our spacious 2 bedroom condo.
ID#: 49
From $1,400 /Week

61 Reviews
Beautiful Three Bedroom Townhome Anna Maria Island - Monthly Stays
OFFER
Beautiful Three Bedroom Townhome Anna Maria Island - Monthly Stays
South West FL > Anna Maria Island > Holmes Beach
Townhouse , Bedroom(s): 3 , Sleeps: 6
Beautiful townhome steps from the beach and walking distance to all things "BEACH"...our location is one of the most sought after on the island.
ID#: 2220

0 Reviews

OFFER We are monthly booking only, if you choose to book two months with us we will discount your stay.

Special offer period: Apr 25, 2021 - Aug 25, 2022

Direct Gulf Front Condo
Direct Gulf Front Condo
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 1 , Sleeps: 4
Walk out your door and onto the beach on beautiful Anna Maria Island!
ID#: 2226
From $200 /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
The Anna Maria Island Beach Palms 2B
The Anna Maria Island Beach Palms 2B
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 4
FAMILY/CHILD FRIENDLY CONDOMINIUM.
ID#: 1767
From $121 /Night

0 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
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
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
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