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Boat Friendly, Family Friendly in Florida

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Chic on the Beach
From $2,000 /Week
Villa
Anna Maria Island > Holmes Beach
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
Spanish Key 207 - Perdido Key Beachfront Condo Rental
Condo
North West FL > Perdido Key
Sailmaker 903 Penhouse Beachfront Condo in Perdido Key
Condo
North West FL > Perdido Key
Grand Caribbean 417W - Steps to Beach Huge Pool and Hot Tub
Condo
North West FL > Perdido Key
Gulfside Villa 2D - Beautiful Beachfront Condo in Perdido Key
Condo
North West FL > Perdido Key
Gulfside Villa 2C - Gorgeous Beachfront Condo in Perdido Key!
Condo
North West FL > Perdido Key
Indigo East 905
Condo
North West FL > Perdido Key
Windemere 706
Condo
North West FL > Perdido Key
Perdido Sun 714
From $115 /Night
Condo
North West FL > Perdido Key
Ocean Breeze East 402
Condo
North West FL > Perdido Key
Ocean Breeze West 502
Condo
North West FL > Perdido Key
Sandy Key 224
Condo
North West FL > Perdido Key
Sandy Key 826
Condo
North West FL > Perdido Key
Sandy Key 735 - Perdido Key Beachfront Pool and Hot Tub
Condo
North West FL > Perdido Key
Sandy Key 227
Condo
North West FL > Perdido Key
Sandy Key 637
Condo
North West FL > Perdido Key
Sandy Key 516
Condo
North West FL > Perdido Key
Sandy Key 423
Apartment
North West FL > Perdido Key
Gone Gulfing - Shore Fun - Golf Included!*
Townhouse
North West FL > Perdido Key
Seasons in the Sun - Golf Course, Private Beach Club, Olympic-size Pool
Townhouse
North West FL > Perdido Key
Sunset Views - Lost Key Golf Course and Beach Club Rentals
Townhouse
North West FL > Perdido Key
Above Par - Perdido Key Vacation Rental includes Golf and Private Beach Club!
Condo
North West FL > Perdido Key
Beach Colony East 8D - Perdido Key Beachfront Condo
Condo
North West FL > Perdido Key
Beach Colony East Penthouse 1D - Indoor - Outdoor Pools, Tennis, Fitness Center and more!
Condo
North West FL > Perdido Key
Beach Colony East 13D - Perdido Key Beachfront Condo
Condo
North West FL > Perdido Key
Resort Life at Esplanade Lakewood Ranch - Monthly Stays
From $2,000 /Month
Condo
South West FL > Bradenton
Sailmaker 903 Penhouse Beachfront Condo in Perdido Key
Sailmaker 903 Penhouse Beachfront Condo in Perdido Key
North West FL > Perdido Key
Condo , Bedroom(s): 5 , Sleeps: 10
Everything you need for Family Gatherings
ID#: 1457

2 Reviews
Aug Dates Open! - Waterfront Pool Hot Tub Dock Sauna - Steps to the Beach
Aug Dates Open! - 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
Aug Dates Open! - Htd Pool Waterfront Dock Ping Pong Outdoor Bar Backyard Beach
Aug Dates Open! - 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
Aug 8 - 15 Open! - Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
Aug 8 - 15 Open! - 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

62 Reviews
Key Colony Vacation Rental by Owner from $800 week
Key Colony Vacation Rental by Owner from $800 week
Florida Keys > Marathon Area > Key Colony Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Tads Place is a 2 bed 2 bath vacation rental here in Key Colony Beach.
ID#: 1019
From $800 /Week

0 Reviews
Marco Memories
Marco Memories
South West FL > Marco Island
House , Bedroom(s): 4 , Sleeps: 10
Waterfront Vacation Home with Southwest Exposure. 4 Bedroom, 4 full bath home with 3500 square feet is perfect for 2 families or one large one. No Red Tide !
ID#: 347
From $275 /Night

16 Reviews
Palm Harbor - Florida Keys Monthly Vacation Rental with Dock
Palm Harbor - Florida Keys Monthly Vacation Rental with Dock
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 3 , Sleeps: 6
Palm Harbor located at mile marker 23 in Cudjoe Gardens is the perfect spot to unwind and relax in the Florida Keys sunshine!This rental is a monthly rental.
ID#: 1526
From $4,000 /Month

0 Reviews
Privacy On Sombrero Beach With Heated Pool, Deep Water Dock, Ocean View
Privacy On Sombrero Beach With Heated Pool, Deep Water Dock, Ocean View
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 5 , Sleeps: 12
Located on Sombrero Beach area of Marathon, just 50 min from Key West is our Florida Keys
ID#: 403
From $3,500 /Week

6 Reviews
Family Retreat Florida Keys - Perfect for Large Groups - Private Beach and Pool!
Family Retreat Florida Keys - Perfect for Large Groups - Private Beach and Pool!
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 6 , Sleeps: 14
House, 6 Bedrooms + Sunroom, 4 Baths, (Sleeps 12-16)
ID#: 1470
From $691 /Night

10 Reviews
Another Day In Paradise - Florida Keys Boaters Monthly Rental
Another Day In Paradise - Florida Keys Boaters Monthly Rental
Florida Keys > Lower Keys Area > Summerland Key
House , Bedroom(s): 3 , Sleeps: 8
It’s more than just another Day in Paradise, it’s an incredibly wonderful and memorable vacation stay in the fabulous Florida Keys! Monthly rental only!
ID#: 1511
From $7,500 /Month

0 Reviews
Egret's Landing - Affordable Cudjoe Key Monthly Rental with Dock
Egret's Landing - Affordable Cudjoe Key Monthly Rental with Dock
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 3 , Sleeps: 6
Just off Cudjoe Bay, you're only a short distance from fabulous Looe Key, one of the best diving and snorkeling sites in the Lower Florida Keys! Monthly rental
ID#: 1519
From $3,700 /Month

0 Reviews
5 Pirates Hideaway Canal Front Home wPrivate Pool and Seawall for your boat
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 6-8 people)
ID#: 1988
From $200 /Night

0 Reviews
Breezy Palms - Florida Keys Monthly Vacation Rental with Dock
Breezy Palms - Florida Keys Monthly Vacation Rental with Dock
Florida Keys > Lower Keys Area > Little Torch Key
House , Bedroom(s): 3
Enjoy all the best the Keys have to offer at this super special Little Torch vacation rental home. This home is a monthly rental only!
ID#: 1516
From $4,800 /Month

0 Reviews
The Fancy Fisherman - Little Torch Key Monthly Rental with Dock
The Fancy Fisherman - Little Torch Key Monthly Rental with Dock
Florida Keys > Lower Keys Area > Little Torch Key
House , Bedroom(s): 3 , Sleeps: 6
Come experience comfortable waterfront living with immediate access to some of the best fishing waters around! This rental is a vacation rental only.
ID#: 1520
From $4,400 /Month

0 Reviews
Bahia Azul - Private Sandy Beach - Florida Keys Monthly Vacation Rental
Bahia Azul - Private Sandy Beach - Florida Keys Monthly Vacation Rental
Florida Keys > Lower Keys Area > Ramrod Key
House , Bedroom(s): 4 , Sleeps: 8
Bahia Azul, "Bay of Blue" is exactly the perfect spot for your next Florida Keys adventure.This home is a monthly rental only!
ID#: 1513
From $7,400 /Month

0 Reviews
Marco Island on the Water Newly renovated 3 bedroom 2 bath with beautiful waterviews
Marco Island on the Water Newly renovated 3 bedroom 2 bath with beautiful waterviews
South West FL > Marco Island
House , Bedroom(s): 3 , Sleeps: 8
Beautiful Marco Island Boat Friendly Vacation Rental with Dock, pool and beautiful water views.
ID#: 1137
From $200 /Night

0 Reviews
Little Torch Key Nest
Little Torch Key Nest
Florida Keys > Lower Keys Area > Little Torch Key
House , Bedroom(s): 6 , Sleeps: 12
This Lower Keys 6BR/4.5 getaway has a private boat basin and ramp, a pool, and a separate guest house with its own kitchen and living room.
ID#: 2024
From $571 /Night

0 Reviews
Salty Retreat- Florida Keys Monthly Vacation Rental with Tiki Hut, Pool and Dock
Salty Retreat- Florida Keys Monthly Vacation Rental with Tiki Hut, Pool and Dock
Florida Keys > Lower Keys Area > Summerland Key
House , Bedroom(s): 3 , Sleeps: 8
Come live the Salt Life at Salty Retreat! Stay at this luxury pool home on Summerland Key with tiki hut and dock This rental is a monthly rental.
ID#: 1528
From $12,500 /Month

0 Reviews
Sea Life Happy - Heated Pool Spa Dock Waterfront Steps to Beaches - Pine Ave
Sea Life Happy - Heated Pool Spa Dock Waterfront Steps to Beaches - Pine Ave
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
Minimum stay: 7-nights Sleeps: 8 maximum Bedrooms: 4 Bathrooms: 3 Private Home Waterfront Dock Hot Tub Wifi Internet No Pets
ID#: 25
From $2,475 /Week

48 Reviews
Palm Villa- Little Torch Key Monthly Vacation Rental with Dock
Palm Villa- Little Torch Key Monthly Vacation Rental with Dock
Florida Keys > Lower Keys Area > Little Torch Key
Villa , Bedroom(s): 3 , Sleeps: 6
This beautiful custom home located in Jolly Rodger subdivision on Little Torch Key has the best of everything! This rental is a monthly rental.
ID#: 1527
From $6,100 /Month

0 Reviews
Mermaid's Rest- Cudjoe Key Monthly Rental
Mermaid's Rest- Cudjoe Key Monthly Rental
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 3 , Sleeps: 6
Cudjoe Key Pet Friendly - Boat Friendly monthly vacation rental in the Gorgeous Florida Keys
ID#: 1525
From $4,000 /Month

0 Reviews
Hawkins Heaven - Florida Keys Waterfront Monthly Rental with Dock
Hawkins Heaven - Florida Keys Waterfront Monthly Rental with Dock
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 2 , Sleeps: 4
Come stay at this heavenly oasis!This rental is a monthly rental only
ID#: 1522
From $3,900 /Month

0 Reviews
Bernie's Bungalow- Florida Keys Waterfront Monthly Rental
Bernie's Bungalow- Florida Keys Waterfront Monthly Rental
Florida Keys > Lower Keys Area > Big Pine Key
House , Bedroom(s): 2 , Sleeps: 4
Come stay at this charming tropical style bungalow. This rental is a monthly rental only! Snowbirds Welcome!
ID#: 1514
From $3,400 /Month

0 Reviews
Buccaneer Boathouse - Florida Keys Monthly Rental
Buccaneer Boathouse - Florida Keys Monthly Rental
Florida Keys > Lower Keys Area > Little Torch Key
House , Bedroom(s): 2 , Sleeps: 4
Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys! Monthly rental.
ID#: 1517
From $3,400 /Month

0 Reviews
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
ID#: 1228
From $290 /Night

10 Reviews
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