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Boat Friendly, Family Friendly in Florida

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Historic Gem in the heart of Jupiter Florida
From $160 /Night
House
Southeast FL > Jupiter
Piece of Paradise - Oceanfront Vacation Rental - Boat Friendly!
From $500 /Night
Villa
Florida Keys
Oceanfront Corner, North Hutchinson Island
From $3,900 /Month
Condo
East Central FL > Hutchinson Island
Beachfront -Direct ocean view - Apollo 306
From $225 /Night
Condo
South West FL > Marco Island
Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
From $447 /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
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 $386 /Night
House
Anna Maria Island > Anna Maria
Two Minute Walk to Lazy River! • Free Pool Heat • ChampionsGate • Golf
From $300 /Night
House
Central FL, Orlando Area, Disney > Davenport
Luxurious Islamorada ,Private Sandy Beach Access. Hammocks, Kayaks, & More!
From $486 /Night
House
Islamorada Area > Islamorada
Luxury and Location! Fully Equipped. 2-Minute Stroll to Gulf Beach.
From $365 /Night
Townhouse
Anna Maria Island > Bradenton Beach
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
LAST MINUTE DISCOUNTED RATES AT BLUE TURTLE COTTAGE FOR AVAILABLE DATES IN AUGUST!!
From $256 /Night
House
Anna Maria Island > Holmes Beach
Edge of Paradise at Margaritaville - 5 Night Min - monthly's wanted
OFFER
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
Luxurious Islamorada ,Private Sandy Beach Access. Hammocks, Kayaks, & More!
Luxurious Islamorada ,Private Sandy Beach Access. Hammocks, Kayaks, & More!
Florida Keys > Islamorada Area > Islamorada
House , Bedroom(s): 3 , Sleeps: 6
Newly renovated and remodeled, private sandy beach, waterfront location, tiki, hammocks and tons of sports gear for guests!
ID#: 329
From $486 /Night

5 Reviews
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 $447 /Night

4 Reviews
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 $386 /Night

20 Reviews

OFFER October Get Away - $300/per Night, 4 Night Minimum

Special offer period: Oct 3, 2020 - Oct 31, 2020

Beachfront condo on Siesta Key
Beachfront condo on Siesta Key
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
Updated beachfront condo directly on the sands of Turtle beach
ID#: 2056
From $1,195 /Week

1 Reviews
Beachfront -Direct ocean view - Apollo 306
OFFER
Beachfront -Direct ocean view - Apollo 306
South West FL > Marco Island
Condo , Bedroom(s): 1 , Sleeps: 4
Enjoy your private deck and view of the ocean.
ID#: 2075
From $225 /Night

0 Reviews

OFFER $225/night. 5 night minimum. (plus required taxes and cleaning fee).

Special offer period: Oct 10, 2020 - Oct 17, 2020

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
Oct 3 - Oct 10 Deal! - Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
OFFER
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

OFFER Oct 3 - Oct 10, 2020 - 7 night deal - $1,799 plus fees and taxes

Special offer period: Jul 22, 2020 - Oct 10, 2020

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
Piece of Paradise - Oceanfront Vacation Rental - Boat Friendly!
OFFER
Piece of Paradise - Oceanfront Vacation Rental - Boat Friendly!
Florida Keys
Villa , Bedroom(s): 5 , Sleeps: 10
Gorgeous views/Luxurious/Spacious 5 bedroom 3 1/2 bath single villa located in Hawks Cay Resort. Oceanfront/view with pool, rooftop deck, Free WIFI, Fireplace.
ID#: 2089
From $500 /Night

1 Reviews

OFFER Fall 2020

Special offer period: Sep 16, 2020 - Dec 18, 2020

Historic Gem in the heart of Jupiter Florida
Historic Gem in the heart of Jupiter Florida
Southeast FL > Jupiter
House , Bedroom(s): 2 , Sleeps: 6
True & timeless peace filled oasis, steeped with history in it's homeyness. Steps from the action of a vibrant town, glorious beaches, golf, boating & parks.
ID#: 2095
From $160 /Night

0 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
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
South Point Shores - Florida Keys Monthly Rental with Dock
South Point Shores - Florida Keys Monthly Rental with Dock
Florida Keys > Lower Keys Area > Sugarloaf Key
House , Bedroom(s): 3 , Sleeps: 6
This bright, very spacious and inviting, nicely-maintained Sugarloaf Key home is located just 20 minutes north of Key West!This rental is a monthly rental only!
ID#: 1529
From $5,300 /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 adults)
ID#: 1988
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 $575 /Night

1 Reviews
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
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
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
Elegant and spacious waterfront condominium
Elegant and spacious waterfront condominium
South West FL > Marco Island
Condo , Bedroom(s): 2 , Sleeps: 4
Elegant and spacious waterfront condominium
ID#: 1000
From $1,090 /Week

6 Reviews
5 O'Clock Somewhere - Florida Keys Monthly Rental with Dock
5 O'Clock Somewhere - Florida Keys Monthly Rental with Dock
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 2 , Sleeps: 4
It's always 5 O'Clock here at this wonderful Florida Keys vacation spot! This rental is a monthly rental only!
ID#: 1521
From $3,300 /Month

0 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
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
Gulf View End Unit Only 60 Steps to Beach - Pet Friendly - Lots of Extras!
Gulf View End Unit Only 60 Steps to Beach - Pet Friendly - Lots of Extras!
North West FL > Cape San Blas
Condo , Bedroom(s): 2 , Sleeps: 6
Water's Edge Barrier Dunes 177 is a fabulous gulf view town home only 60 steps to the beautiful white sand beaches of Cape San Blas.
ID#: 736
From $150 /Night

12 Reviews
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