Boat Friendly in Florida

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.
From $1,799 /Week
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.
From $1,999 /Week
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!
From $1,799 /Week
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 !
From $275 /Night
Waterfront, Open Gulf Access, Dock, Pool, Spa, Wraparound Deck View of Sunsets & Sunrises
OFFER
Waterfront, Open Gulf Access, Dock, Pool, Spa, Wraparound Deck View of Sunsets & Sunrises
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 3 , Sleeps: 8
Fisherman's Easy Access to Gulf, Waterfront, 60 ft Dock, Pool, Hot Tub, Sleeps 8
From $249 /Night
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
From $290 /Night
Summerland Beach-Boat Lift 120' of seawall for your large or small boat
Florida Keys > Lower Keys Area > Summerland Key
House , Bedroom(s): 4 , Sleeps: 8
4 Bedroom, 4 1/2 Bath Pool Home With Boatlift and 120' of Seawall for Large or Small Boats
From $13,000 /Month
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
From $3,500 /Week
The Closest Condo to the Gulf of Mexico on Siesta Key
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
We are directly on the beach. The Gulf of Mexico is about 125' from our lanai and the Bay inlet is about 100' from our guest bedroom window and east balcony.
From $1,195 /Week
New Build-4 bd3 bath-Private pool & dock-Paradise Found!
OFFER
New Build-4 bd3 bath-Private pool & dock-Paradise Found!
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 4 , Sleeps: 10
4 Bds/3 baths/Heated Pool/Dock/Canal Way/Sombrero Beach
From $457 /Night

OFFER Paradise Found!

Special offer period: May 30, 2020 - Aug 31, 2020

"Get Hooked" in Family Friendly Marathon Special Pricing available
Florida Keys > Marathon Area > Marathon
Villa , Bedroom(s): 4 , Sleeps: 10
4 bedroom/3 bath Canal front home. License #plr2016-0027
From $265 /Night
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.
From $12,500 /Month
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)
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
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
From $2,475 /Week
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)
From $691 /Night
EMAIL WITHIN FOR ALL INQUIRES DIRECT OCEANFRONT JEWEL,Heated Salt  Pool,70Ft Doc
OFFER
EMAIL WITHIN FOR ALL INQUIRES DIRECT OCEANFRONT JEWEL,Heated Salt Pool,70Ft Doc
Florida Keys > Islamorada Area > Islamorada
House , Bedroom(s): 4 , Sleeps: 12
House, 4 Bedrooms, 3 Baths, (Sleeps 2-12), Heated salt water pool. 70+ ft deep water dock, Screened in upper porch, lower outside bar with tv and bbq.
From $400 /Night

OFFER Special Summer and Fall rates

Special offer period: Jun 1, 2020 - Dec 19, 2020

SIESTA KEY CONDO-DIRECT OCEAN FRONT, 8TH FLOOR, LUXURY, SPACIOUS, BEST VIEW
OFFER
SIESTA KEY CONDO-DIRECT OCEAN FRONT, 8TH FLOOR, LUXURY, SPACIOUS, BEST VIEW
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 4
2 bedroom, 2 bath, 8th floor, beautiful furniture and accessories, well-appointed condo directly overlooking the ocean on Siesta Key. Min 2 weeks stay required.
From $1,200 /Week

OFFER SPECIAL OFFER! $100 OFF PER WEEK off our already low discounted rates - 2 week minimum. $1200 per week; $2400 for the 2 week minimum stay. Come enjoy Paradise in our beautiful, immaculate and spacious condo directly facing the ocean and beach in Siesta Key. Transport yourself to another "world" where you can totally relax and let the stresses of the day melt away.

Special offer period: Jul 1, 2020 - Jul 15, 2020

Luxury 2400 sq ft 6th floor condo with private access to Crescent Beach
South West FL > Siesta Key
Condo , Bedroom(s): 3 , Sleeps: 6
Large open floor plan is great for family vacations. Location...Location...Location !! Everything is within walking distance.
From $1,690 /Week
Lemon Key Cottage
Florida Keys > Marathon Area
House , Bedroom(s): 2 , Sleeps: 6
Private Waterfront Heated Pool Home: 60' Dock: Direct Ocean Access: Kayaks: Beach
From $195 /Night
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
Keys Living
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 4 , Sleeps: 8
3 BR 2BA With Private Pool, Tiki Bar w/screened in porch/TV, 2 Kayaks/ Oceanside
From $315 /Night
Keys Dreaming
OFFER
Keys Dreaming
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 4 , Sleeps: 10
Spectacular 4BR/3BA home on canal near Sombrero Beach, fishing, and shopping
From $286 /Night

OFFER Fall specials August to mid Dec excl holiday weeks $2000/wk + fees. Book today!

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

Fishermans Cove A102 - On Turtle Beach on Siesta Key
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
Fishermans Cove A102 - On Turtle Beach on Siesta Key
From $1,150 /Week
Fall Openings! Turtle Cove - Pool and Hot Tub, Quick Atlantic Access!
OFFER
Fall Openings! Turtle Cove - Pool and Hot Tub, Quick Atlantic Access!
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 3 , Sleeps: 8
Escape to the Keys ~ Located in Marathon, waterfront, pool & hot tub, single family home. 3 bed / 2 bath, dockage with quick ocean access.
From $1,925 /Week