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Florida Keys Rentals

$Ocean Front 2\/2 Condo,OCEAN FRONT\/MARINA VIEW,Tavernier\/Key Largo Fl. Fla.Keys$
From $357 per night (USD)
VRBO
Ocean Front 2\/2 Condo,OCEAN FRONT\/MARINA VIEW,Tavernier\/Key Largo Fl. Fla.Keys
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to Paradise! Discover the pinnacle of luxury at Ocean Pointe, a premier resort nestled in Tavernier, Florida Key ...
From $357 per night (USD)
VRBO
From $638 per night (USD)
Expedia
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
** The Marina is repairing all of the canal boat slips currently BUT you can reserve a slip at the marina right there fo ...
From $638 per night (USD)
Expedia
From $525 per night (USD)
VRBO
Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This gorgeous 3 bedroom 3 full bath townhouse is located in the tropical neighborhood of Kawama. This unit underwent a f ...
From $525 per night (USD)
VRBO
From $649 per night (USD)
Expedia
Manatee Watch | Gorgeous pool, 5 bedrooms, easy ocean access on Big Pine Key
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offer ...
From $649 per night (USD)
Expedia
From $522 per night (USD)
VRBO
P23 - New 3 bedroom 2 bath duplex with private pool and deep water dockage.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This all ground level home boasts ease of access inside and out, with an open floor plan and a large, fully equipped kit ...
From $522 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Serene Sunsets Await - Tropical Island Getaway Without The Extensive Travel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BOAT SLIP Available for ALL Lobster Seasons..! January 2025 Updates: Unbelievable...! Word to describe the upgrades ...
From $248 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Ground floor no stairs close to everything Atlantic side
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A fisherman's dream boat dock freezers for your catch commercial icemaker fish cleaning station backyard grill fully s ...
From $351 per night (USD)
VRBO
From $714 per night (USD)
Expedia
Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
** The Marina is repairing all of the canal boat slips currently BUT you can reserve a slip at the marina right there ...
From $714 per night (USD)
Expedia
From $853 per night (USD)
VRBO
Villa Jekjak | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy the unobstructed 270-degree ocean view in this newly renovated beachfront residence. Located in the most exclusive ...
From $853 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Beautiful updated Kawama Townhouse. Two units available. Second unit #1306961.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This gorgeous 3 bedroom 3 full bath townhouse is located in the tropical neighborhood of Kawama. This unit underwent a ...
From $525 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful & Relaxing 2 bed 2 bath condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a large 2 bed 2 bath condo with a separate living room, kitchen, and private balcony at the Hyatt Resort. It off ...
Click For Pricing
VRBO
From $596 per night (USD)
Expedia
Island Adventure I 4 Bedrooms 4.5 Baths, Pool, Ocean View with Dock & Kayaks
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
VACA-22-75 Welcome to Island Adventure: Your Ultimate Florida Keys Retreat *Island Adventure* is the perfect home for ...
From $596 per night (USD)
Expedia
$Aqua Lodge Houseboat \Sea Turtle\$
From $354 per night (USD)
VRBO
Aqua Lodge Houseboat \"Sea Turtle\"
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to The Aqua Villas at Mangrove Marina Resorts “Sea Turtle” houseboat, located between Key Largo and Islamorada i ...
From $354 per night (USD)
VRBO
From $752 per night (USD)
Expedia
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated a ...
From $752 per night (USD)
Expedia
From $1326 per night (USD)
VRBO
All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome aboard the The Thirsty Lady with 3 bedrooms and 3 baths, your own private Sailboat that also includes your Saili ...
From $1326 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Cudjoe Bay Getaway In Paradise
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our house in paradise! This elevated canal house is the fourth property away from Cudjoe Bay and the Atlantic ...
From $235 per night (USD)
Expedia
$Aqua Lodge Houseboat \Calypso\$
From $486 per night (USD)
VRBO
Aqua Lodge Houseboat \"Calypso\"
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
It doesn’t get much more unique than the Aqua Villas at Mangrove Marina. Come experience the adventure of living on the ...
From $486 per night (USD)
VRBO
$Aqua Lodge Houseboat \Captain's Quarters\$
From $441 per night (USD)
Expedia
Aqua Lodge Houseboat \"Captain's Quarters\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Aqua Villas at Mangrove Marina Resorts “Captain’s Quarters” houseboat, located between Key Largo and Isla ...
From $441 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Sunsets over the water
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sunset views over the water has this large 1/1 with 1 assigned parking space. Only a few minutes from the Island of Key ...
From $144 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
City of Marathon zoning requires a minimum rental period of 7 nights, and no exceptions can be made. Please review addit ...
From $250 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Spectacular Water Front Home! Key Largo, Ocean side, Sea Breeze
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Breathtaking concrete home with 2,200SF A/C and 6,900SF lot, freshly remodeled with elegance having large impact windows ...
From $521 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Tarpon Tales | Pet-friendly home with fantastic boating access on Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
An angler's dream! Comfy 2 bedroom / 2 bathroom home on a large and lush canalfront property just minutes from the chann ...
From $193 per night (USD)
Expedia
$Casa Playa | 4 bed\/2 bath canalfront getaway on Ramrod Key$
From $237 per night (USD)
VRBO
Casa Playa | 4 bed\/2 bath canalfront getaway on Ramrod Key
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Casa Playa, your spacious 4-bedroom, 2-bathroom retreat nestled in the serene beauty of Ramrod Key. This invi ...
From $237 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
As you step through the door, you are enveloped in a serene atmosphere highlighted by soothing tropical colors and impre ...
From $475 per night (USD)
Expedia
$Aqua Lodge Houseboat \The Grey Lady\$
From $506 per night (USD)
VRBO
Aqua Lodge Houseboat \"The Grey Lady\"
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This houseboat has 2 Queen beds, 1 Double bed and 1 Twin bed. The houseboat has a flat-screen TV with cable in the livin ...
From $506 per night (USD)
VRBO
From $660 per night (USD)
Expedia
Key West Beach House with heated pool, tiki, and dock.♿︎
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to Key West. Located on this beautiful island 13 miles from downtown is this quaint 2-level beach home. With sle ...
From $660 per night (USD)
Expedia
From $585 per night (USD)
VRBO
The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room for Everyone & Fido!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $585 per night (USD)
VRBO
$Key Largo large 4\/3 Waterfront home access to the Bay$
From $291 per night (USD)
Expedia
Key Largo large 4\/3 Waterfront home access to the Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Beautiful New Home on the water in the Florida Keys. Mile marker 103. 4 bedrooms all newly furnished, 3 full bathroom, ...
From $291 per night (USD)
Expedia
From $130 per night (USD)
VRBO
NEWLY RENOVATED Key Largo Beach Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Immerse into this private beach-style cottage that has stunning bay views and is a minute's walk from a private beach. T ...
From $130 per night (USD)
VRBO
From $520 per night (USD)
Expedia
KEY LARGO BRAND NEW HOUSE WITH POOL & DOCKAGE
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to paradise! This home is a new listing to VRBO. If you are looking for a large beautiful home with a pool in a ...
From $520 per night (USD)
Expedia
$Aqua Lodge Houseboat \Yellow Tail \$
From $380 per night (USD)
VRBO
Aqua Lodge Houseboat \"Yellow Tail \"
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Are you ready to be adventurous , do something unique and fun? Well, it doesn’t get Yellow Tail houseboat, is a 1 bedro ...
From $380 per night (USD)
VRBO
$Aqua Lodge Houseboat \Tarpon\$
From $380 per night (USD)
Expedia
Aqua Lodge Houseboat \"Tarpon\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This Aqua Lodge has a master bedroom with a queen-sized bed, equipped with TV and Air Conditioning unit. The cathedral c ...
From $380 per night (USD)
Expedia
From $409 per night (USD)
VRBO
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! It is not so ...
From $409 per night (USD)
VRBO
From $452 per night (USD)
Expedia
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’re loo ...
From $452 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Casa Del Mar in Venture Out Unit 253
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
VO253 Open Water Views 35' Dockage Sparkling Clean 2Bd/1Ba Vacation Home! THIS IS ONE OF THE NICEST UNITS IN ALL OF VENT ...
From $316 per night (USD)
VRBO
From $590 per night (USD)
Expedia
Island Adventure II 4 Bedrooms 4.5 Baths, Pool, Ocean View with Dock & Kayaks
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
VACA-22-74 Welcome to Island Adventure: Your Ultimate Florida Keys Retreat Built in 2021, *Island Adventure* is the pe ...
From $590 per night (USD)
Expedia
From $689 per night (USD)
VRBO
Flirty Flamingo Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $689 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Runaway Bills | 3 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $248 per night (USD)
Expedia
$Canal front getaway w\/ water view & access to the Cabana Club$
From $398 per night (USD)
VRBO
Canal front getaway w\/ water view & access to the Cabana Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Wave From It All Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $398 per night (USD)
VRBO
From $631 per night (USD)
Expedia
Waterfront Town Home on a Lagoon, Marina, Tennis, Pickleball, Bikes, Kayaks
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
If your dates are not available or if you are looking for two units, check out my other VRBO Unit #2523121. Enter the n ...
From $631 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Waterfront luxury Villa (29) with sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $581 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Key Largo Treasure at Kawama Yacht Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Two bedrooms, each with their own balconies, one overlooks the pool, the other State Park Hardwood Hammock. There is ple ...
From $399 per night (USD)
Expedia
From $628 per night (USD)
VRBO
406 Mariners Club Key Largo | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this elegant island townhome in Mariner's Club, Key Largo's premier resort. Updated and upgraded! This is a ...
From $628 per night (USD)
VRBO
From $758 per night (USD)
Expedia
411 Mariners Club | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Spend tranquil days on the sun-kissed balcony with ocean views! Cool down with a plunge in the pool then make plans to ...
From $758 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Paradise for Rent (Condo and Private Boat Slip) monthly discount for sept & oct
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
We are happy to answer all questions! Tropical settings, beautiful sunset views, do as much as you want to do. Just lay ...
From $243 per night (USD)
VRBO
$Henry's Piece of Paradise on the Ocean in Key West - Weekly \/ Nightly$
From $477 per night (USD)
Expedia
Henry's Piece of Paradise on the Ocean in Key West - Weekly \/ Nightly
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean vi ...
From $477 per night (USD)
Expedia
From $791 per night (USD)
VRBO
131 Mariners Club Key Largo | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Spacious and gracious, 4 bedroom, 3 bath, top floor, corner villa with a jaw-dropping view of the resort's harbor and th ...
From $791 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Weekly Discounts! Canal Home with SwimSpa Pool, Walk to Ocean Front Tiki Bars!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**If you’re looking for larger accommodations, please view our home on the same canal, VRBO # 2413494** Enjoy total pri ...
From $368 per night (USD)
Expedia
$A Cut Above: Updated 3-Bed\/2-Bath Half Duplex with Private Pool & Dockage$
From $491 per night (USD)
VRBO
A Cut Above: Updated 3-Bed\/2-Bath Half Duplex with Private Pool & Dockage
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
A Cut Above is an updated 3-bedroom, 2-bathroom beautifully decorated half duplex in desirable Key Colony Beach. Enjoy t ...
From $491 per night (USD)
VRBO
From $451 per night (USD)
Expedia
Sunset South: First Floor 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $451 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Summer Month's Just Opened Up!!! Canal Front Pool Home in Summerland Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private is ...
From $328 per night (USD)
VRBO
$Seabreeze Marathon Oceanside 4\/3 Pool Boat Dock$
From $734 per night (USD)
Expedia
Seabreeze Marathon Oceanside 4\/3 Pool Boat Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Seabreeze Marathon! Don't look any further for your perfect vacation destination. This property is a newly r ...
From $734 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Sunset views at the Galleon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
From $433 per night (USD)
VRBO
From $1000 per night (USD)
Expedia
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1000 per night (USD)
Expedia
$Upscale Townhome w\/ Golf, Garden & Lake Views, Shared Pool, WiFi - Dogs OK$
From $255 per night (USD)
VRBO
Upscale Townhome w\/ Golf, Garden & Lake Views, Shared Pool, WiFi - Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Tipsy Mermaid at Key West Golf Club Our calendar is updated in real-time & our nightly rates are accurately display ...
From $255 per night (USD)
VRBO
From $460 per night (USD)
Expedia
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $460 per night (USD)
Expedia
From $610 per night (USD)
VRBO
July Opening Waterfront Getaway with Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to our beautiful 4bdrm/ 3 full bath waterfront home. Relax and relish the tropical waters that surround you in p ...
From $610 per night (USD)
VRBO
From $448 per night (USD)
Expedia
Villa Largo Island Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Indulge in endless sun-soaked delights at this stunning property nestled within one of the most sought-after an ...
From $448 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #13 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. SpaciouQuaint, clean, co ...
From $229 per night (USD)
VRBO
$To Paradise \nBook our website fishing & excursions bigdavechartersandtours.com\n$
From $1012 per night (USD)
Expedia
To Paradise \nBook our website fishing & excursions bigdavechartersandtours.com\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Forget your worries in this spacious and serene space. Relax while sitting and watching TV or listening. . to music in ...
From $1012 per night (USD)
Expedia
From $1002 per night (USD)
VRBO
Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1002 per night (USD)
VRBO
$Exquisite Key Colony Beach Retreat- 420\/430 11th Street KCB$
From $1004 per night (USD)
Expedia
Exquisite Key Colony Beach Retreat- 420\/430 11th Street KCB
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Have you been dreaming of a sun-soaked Florida Keys getaway with ample space for your whole family? Turn those dreams in ...
From $1004 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Paradise Without A Passport New Home Ocean Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Brand New Home, Brand New Furniture, Sunset and Ocean Views, Outdoor communal Fire Pits, Outdoor Kitchen, Grill, Possibl ...
From $314 per night (USD)
VRBO
From $887 per night (USD)
Expedia
Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $887 per night (USD)
Expedia
From $1033 per night (USD)
VRBO
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1033 per night (USD)
VRBO
From $931 per night (USD)
Expedia
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $931 per night (USD)
Expedia
From $903 per night (USD)
VRBO
Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $903 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $955 per night (USD)
Expedia
Click For Pricing
VRBO
Oceanfront BEACH HOUSE with DOCKAGE and BOAT LIFT
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a stroll along the dock to watch the rising morning sun, lounge on the dock netting and become entranced by the la ...
Click For Pricing
VRBO
From $961 per night (USD)
Expedia
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $961 per night (USD)
Expedia
From $916 per night (USD)
VRBO
Bayview Middle: Waterfront 3 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $916 per night (USD)
VRBO
From $439 per night (USD)
Expedia
Island Escape at Ocean Pointe
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated unit with fresh paint, updated cabinets in kitchen and bathroom, new ceiling fans. Updated living room ...
From $439 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Marathon 3BR Canal Home w Pool Spa Combo 55' Dock Free pool heat and chiller
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Mirage Manor has had lots of happy visitors, but needed a bigger and better pool. Construction is now complete and rent ...
From $517 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. ...
From $287 per night (USD)
Expedia
$Its an enjoyable two bed\/bath unit with pleasant view of the marina and 0cean.$
From $219 per night (USD)
VRBO
Its an enjoyable two bed\/bath unit with pleasant view of the marina and 0cean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your Newly Renovated Oceanfront Vacation Home: In June 2018, the Condo unit had a total renovation including installati ...
From $219 per night (USD)
VRBO
From $1428 per night (USD)
Expedia
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
New Listing - Family Reunion Large Vacation Rental 6 bedrooms 5 baths steps to Sombrero Beach. 6 bedrooms (5 King size b ...
From $1428 per night (USD)
Expedia
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VRBO
Fantastic Waterfront Location, Beautiful Ocean Views & Near Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a newly renovated ocean front cottage attached to the main house with private pool and boat docking available. ...
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VRBO
$Condo 2br\/2bath waterfront$
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Expedia
Condo 2br\/2bath waterfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
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Expedia
From $187 per night (USD)
VRBO
coral stone
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our apartment offers all the comforts of home, 120 paces to Duval Street - shopping, restaurants and nightlife. Near Hem ...
From $187 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Dog-friendly oceanfront home with private pool, screened porch & outdoor kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Blue Water Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $390 per night (USD)
Expedia
$Amazing Key Largo Paradise 2\/2 Townhouse$
From $477 per night (USD)
VRBO
Amazing Key Largo Paradise 2\/2 Townhouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to the Keys in this 2bedroom 2 bath townhome overlooking a tranquil lagoon. Swim or Snorkel the Saltwater Lagoon, ...
From $477 per night (USD)
VRBO
From $743 per night (USD)
Expedia
VIP LUXURY PENTHOUSE SUITE! - OFFERS KEY LARGO'S BEST PANORAMIC OCEAN VIEWS!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $743 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Spring & summer dates available licensed rental vr #25-0235 NO BOATS
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a legally licensed rental in the Village of Islamorada license # vr 131 The entire condo has been updated ...
From $225 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Stunning Views & Modern Comforts at Ocean Pointe 2215
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in the heart of the Florida Keys, in the picturesque city of Tavernier, this charming oceanfront condo is your i ...
From $317 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Gorgeous Gulf-front home with dock, private pool & gas grill
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sunset Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $596 per night (USD)
VRBO
From $565 per night (USD)
Expedia
Waterfront luxury Villa (59) with sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $565 per night (USD)
Expedia
From $563 per night (USD)
VRBO
3 Bedroom Oceanfront Townhouse in the fabulous Florida Keys
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This townhouse at Key Colony Point is a beautiful holiday location. Key Colony Point is at the corner of Marathon, so yo ...
From $563 per night (USD)
VRBO
From $713 per night (USD)
Expedia
Bayfront Home with Beach & Open Water Views! Amazing Sunsets!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Best kept secret in the Florida Keys! Our many repeat customers and great reviews attest to our gorgeous beachfront prop ...
From $713 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Harbor House 2bed 2bath Open water views & dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Quaint little 2 bedroom 2 bath single family right on Boot Key Harbor! The porch overlooks the harbor where you can sit ...
From $330 per night (USD)
VRBO
From $485 per night (USD)
Expedia
Spotless Fully Renovated Family Home. Free parking WiFi Pool.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our new fully renovated townhouse hosted by HomeAway Premier Partner Roy Svenningsen. This home is located in ...
From $485 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Paradise found at the Key West Golf Club!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee ...
From $211 per night (USD)
VRBO
From $519 per night (USD)
Expedia
BOOKING SMOKING HOT 2025 DEALS NOW!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $519 per night (USD)
Expedia
From $274 per night (USD)
VRBO
STUNNING! Brand New and Unobstructed Bay View with Cabana Club Membership!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2/2 HALF DUPLEX IN KEY COLONY BEACH ON SADOWSKI CAUSEWAY. COMES WITH CABANA CLUB MEMBERSHIP AS WELL. ENJOY THE POOL, BEA ...
From $274 per night (USD)
VRBO
From $1202 per night (USD)
Expedia
Paradise Cove on the Gulf 5 bedroom 3 bath with pool and dockage, kayaks, bikes,
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Vaca-21-484 Paradise Cove on The Gulf is a Florida Keys Paradise for Everyone. This is a modern design home with sleek ...
From $1202 per night (USD)
Expedia
From $611 per night (USD)
VRBO
408 Mariners Club oceanfront | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Sleeps 6 in beds, maximum occupancy 8 ~ Welcome to this spacious, oceanfront 3-bedroom, 3-bath townhouse ideally located ...
From $611 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Egret House @ Tarpon Point
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Indulge in breathtaking ocean vistas from every living level, complemented by an inviting waterfront pool! The ...
From $955 per night (USD)
Expedia
From $712 per night (USD)
VRBO
801 Mariners Club Key Largo | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This newly renovated townhouse is a refined yet Keysey Key Largo vacation rental (Unit 801) is a 2 story townhouse with ...
From $712 per night (USD)
VRBO
From $213 per night (USD)
Expedia
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic fl ...
From $213 per night (USD)
Expedia
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VRBO
FANTASY WEEK
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale re ...
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VRBO
From $725 per night (USD)
Expedia
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
WEEKLY RENTAL: This property has a 7 night minimum stay. **Beginning January, 2026, Fair Winds will be a MONTHLY (28 ni ...
From $725 per night (USD)
Expedia

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