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From $166 per night (USD)
VRBO
NAUTI HIDEAWAY - 2/2, Slip, Private Ramp, Pool, Trailer Parking, Bait Freezer!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Vehicle parking, trailer parking, the private boat ramp, your slip, and the pool are each, at most 200 ft from the cond ...
From $166 per night (USD)
VRBO
From $492 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $492 per night (USD)
Expedia
From $652 per night (USD)
VRBO
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Torchview Lookout – Your Private Waterfront Retreat! Escape to paradise at Torchview Lookout, a secluded 3-b ...
From $652 per night (USD)
VRBO
From $825 per night (USD)
Expedia
**CASA AMARILLA** Old Town Cottage & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $825 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Copacabana, Overlooking the Gulf!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Overlooking the Gulf of Mexico allows for the great views at this beautiful home. Bring your boat or rent one! The new d ...
From $572 per night (USD)
VRBO
From $437 per night (USD)
Expedia
🌇 Ocean Sunset Views with Pool and Dock 🌇
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful two bedroom two bath single family home with pool and spa with dock right on the water! Enjoy the beautiful s ...
From $437 per night (USD)
Expedia
From $584 per night (USD)
VRBO
Oceanside Key Largo Townhome, Private Marina, pools, Tennis and Golf Cart
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Located in the Heart of Key Largo, in a 24 acre private community you will find Kawama Yacht Club which is surrounded by ...
From $584 per night (USD)
VRBO
From $145 per night (USD)
Expedia
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $145 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $151 per night (USD)
VRBO
From $607 per night (USD)
VRBO
Luxurious tropical water-front Heated pool home with Boat Dock and two master .
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Please see the video. This video does not show latest decorations and improvements. Including new tile sunset roof top ...
From $607 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Water front home. 50' Dock w/ Pool & Hot Tub. Just S. of Tavernier Creek
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful Conch style home was completed in 2019. The house is a 2000 sq ft. 3 bedroom 2 bath home, each of it's 3 ...
From $574 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Locate ...
From $307 per night (USD)
Expedia
From $289 per night (USD)
VRBO
~Reel Paradise~Beautiful private townhouse in a small gated community.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $289 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Convenient central Marathon location, canal view.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cute and super clean! One bedroom and one bath, nicely decorated & furnished. Bedroom has queen bed with topper. Bedroom ...
From $192 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Casa de Sueno
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Casa de Sueno is a spacious 5-bedroom, 2.5-bath waterfront retreat on Little Torch Key, perfect for up to 10 g ...
From $467 per night (USD)
VRBO
From $428 per night (USD)
Expedia
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
STEPS TO DUVAL STREET! WALK EVERYWHERE--TO ALL RESTAURANTS, SHOPS AND BARS OF OLD TOWN, KEY WEST!! You wont nee ...
From $428 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Sunbeam Dream 2BR Oceanfront Condo in Florida Keys
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Summary: Escape to Sunbeam Dream, a beautifully curated two-bedroom, two-bath coastal condo at Ocean Pointe Suites in T ...
From $327 per night (USD)
VRBO
From $962 per night (USD)
Expedia
Conch House - Ocean front with dock and pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Conch House is located at mile marker 28.5 on Little Torch Key. You can dock your boat right in your own front yard! ...
From $962 per night (USD)
Expedia
From $250 per night (USD)
VRBO
SEP-DEC SELL-OFF!! OCEANFRONT Lux 1350sf, Great Views &All Amenities of Home!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Rates for remaining available dates in Sep-Dec have just been SLASHED for quick sell-off! Rates are now up to approx. $1 ...
From $250 per night (USD)
VRBO
Click For Pricing
Expedia
Luxurious top floor, end unit, within premier resort on the Atlantic Ocean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax in style at the Hyatt Windward Pointe Resort. This is the best location within the resort: Top floor, end unit. Lo ...
Click For Pricing
Expedia
From $419 per night (USD)
VRBO
OCEANFRONT CONDO w/Lake, 2Kayaks, 2Paddleboards, 2Bikes, Tennis, Boat Ramp
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy a Key Largo adventure in our deluxe oceanfront condo WHICH INCLUDES 2 KAYAKS, 2 PADDLEBOARDS, 2 BIKES, TENNIS RACK ...
From $419 per night (USD)
VRBO
From $583 per night (USD)
Expedia
Blue Paradise 5bed/5bath walking distance to the beach with a private pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
License #: Vaca-20-106 Welcome to Blue Paradise: Your Dream Getaway in the Heart of Sombrero! Escape to luxury and com ...
From $583 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Gulf Getaway | Condo w/Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2. ...
From $279 per night (USD)
VRBO
From $590 per night (USD)
Expedia
Coral Lagoon Updated Single Family Home with 40' Boat Slip directly behind home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to paradise! The Silly Sailfish is 1 of 8 stand-alone single-family homes within the 25-unit Coral Lagoon commun ...
From $590 per night (USD)
Expedia
Click For Pricing
VRBO
Poolside townhouse in Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 2 bed/2.5 bath townhome in key west golf club. Pool steps away. Gated community. Enjoy everything beautiful Ke ...
Click For Pricing
VRBO
From $524 per night (USD)
Expedia
Newly renovated coastal home; Marina, Pools, Lagoon, Bikes, Tiki’s and More!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy your Florida Keys vacation in this upgraded modern coastal home that is waterfront to a saltwater lagoon. Boater's ...
From $524 per night (USD)
Expedia
From $817 per night (USD)
VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $817 per night (USD)
VRBO
From $1108 per night (USD)
Expedia
The Mesa House - One block from Duval St
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else ...
From $1108 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Turquoise Lagoon LLC, wide open turquoise views of the lagoon
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Great view of the lagoon/bay right from the living room and out on the porch. Watch dolphins and manatees and fish jump. ...
From $233 per night (USD)
VRBO
From $365 per night (USD)
Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Community Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $365 per night (USD)
Expedia
From $724 per night (USD)
VRBO
Dolfan Oceanfront Cottage Direct oceanfront with 50 ft of dockage and jacuzzi and kayaks 4 bed 2 bath home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vaca-21-243 This beautiful and spacious home has Direct Oceanfront Living. Ocean views and deep water dockage with boa ...
From $724 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Oceanside Getaway: Beautiful Home with Boat Slip, Pool & Beach - Gated community
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Palm La Mar, a luxury vacation rental located in the exclusive oceanfront gated community of Anglers Reef in Islamorada, ...
From $409 per night (USD)
Expedia
From $546 per night (USD)
VRBO
123 Mariners Club Perl of the Sea Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
If you are looking for the hottest spot in Key Largo, then look no more. The first impression of 123 Mariners Club is qu ...
From $546 per night (USD)
VRBO
From $381 per night (USD)
Expedia
CASA NAUTICA @ KEY COLONY BEACH•GATED TIKI BACKYARD•CABANA BEACH CLUB WITH POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to CASA NAUTICA-KCB, where paradise awaits you with a beautiful 2 bedroom, 2 bath cottage style retreat with exc ...
From $381 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Florida Keys Chic
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy breathtaking sunsets from your very own private beach in this Florida Keys Chic townhome!!! Beautiful 3 bedroom 2 ...
From $214 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Waterfront Oasis w/ Pool, Tiki Lounge, Dock & BBQ
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover your dream vacation in this freshly remodeled 3-bedroom, 2-bath gem on a stunning flow-through canal with direc ...
From $399 per night (USD)
Expedia
From $933 per night (USD)
VRBO
Little Torch Key Nest - Ocean view with pool
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
This Lower Keys 6BR/4.5 getaway has a private boat basin and ramp, a pool, and a separate guest house with its own kitch ...
From $933 per night (USD)
VRBO
From $733 per night (USD)
Expedia
Cloud Suite on Duval Street with Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Cloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of ...
From $733 per night (USD)
Expedia
From $472 per night (USD)
VRBO
Canal front with Pool & 50 feet of Dock on each side / Cabana Club Included!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
DUPLEX, THIS LISTING NUMBER IS 1275459 OTHER SIDE LISTING IS 561552. EACH SIDE HAS 4 BEDROOMS 3 BATHS, YOUR OWN POOL AND ...
From $472 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Casita Key Largo Getaway: Your Gateway to Reefs, Sunsets, and Island Bliss!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Casita Key Largo, your updated tropical escape in the heart of the Upper Keys! Recently refreshed and perfec ...
From $280 per night (USD)
Expedia
From $817 per night (USD)
VRBO
Waterfront Home in Islamorada with outdoor kitchen, pool, spa, boat dockage
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to Tut’s Cay located in Islamorada in the Florida Keys. Our home is centrally located in our favorite part of th ...
From $817 per night (USD)
VRBO
From $285 per night (USD)
Expedia
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Mango Tree Cottage – Old Town Key West Gem! Location, Location, LOCATION! Welcome to The Mango Tree Cottage, your ...
From $285 per night (USD)
Expedia
From $652 per night (USD)
VRBO
Beachside @ Torchview Waterfront Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Beachside at Torchview Located on the serene shores of Big Torch Key in the Florida Keys Beachside at Torchv ...
From $652 per night (USD)
VRBO
From $259 per night (USD)
Expedia
A Peace of Paradise at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This second floor end unit was completely remod ...
From $259 per night (USD)
Expedia
From $794 per night (USD)
VRBO
**CASA SERENDIPITY @ OLD TOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $794 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Peace and tranquility on this lakefront pool home in Buccaneer Point, Key Largo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private house with a pool on the lake in Buccaneer Point, Key Largo. Very quiet neighborhood on a closed lake. 3 bedroo ...
From $391 per night (USD)
VRBO
From $869 per night (USD)
VRBO
Fisherman's Paradise
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Property has 250 feet of dock, greatest fishing in the keys, right off the dock. Mile Marker 53 only 1 hour from Key Wes ...
From $869 per night (USD)
VRBO
From $224 per night (USD)
Expedia
**SERENITY ON SOUTHARD @ THE ANNEX** Condo + Last Key White Glove Service...
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SERENITY ON S ...
From $224 per night (USD)
Expedia
From $368 per night (USD)
VRBO
FALL SPECIALS Now Available- 3bdr./3ba. UPDATED HOME canal access to Sombrero
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Start planning your perfect escape to the Florida Keys! Blue Ocean Bungalow is ideally located on a wide, deep-water can ...
From $368 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Blue Breeze
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Grassy Key Family Friendly Home to Get Away From it All! This Grassy Key home has open-water views of both the ...
From $394 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Amazing Sombrero Beach house-Pool, Kayaks, Bikes & More, great vacation home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
New beach house clean and ready for renters. Accessible to beautiful Sombrero Beach via bike, car, kayak or walk. Priv ...
From $543 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Canal side location with beach & pool club membership!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 2 Bedroom/2 Bath Duplex is perfect for your vacation in paradise or winter getaway! The house can sleep 6. There is ...
From $347 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Designer Comforts & Ocean Views- Ocean Pointe 2416
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Experience Island Living at Ocean Pointe Suites, located directly on the Atlantic Ocean. This end unit is loca ...
From $344 per night (USD)
VRBO
From $901 per night (USD)
Expedia
Waterfront Home, 200ft Dock, Gulf Access, Kayaks, Bicycles, Mini Golf, Game Room
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
WELCOME TO SOL MATE VACATION HOME - MARATHON, FLORIDA KEYS Welcome to Sol Mate Vacation Home, your private waterfront r ...
From $901 per night (USD)
Expedia
From $469 per night (USD)
VRBO
802 Mariners Club - Immaculate 2 bedroom townhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Take a deep breath…enter…and exhale…you have arrived. A bright and immaculately clean home, 802 Mariner's Club is the pe ...
From $469 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Castaway Key - Oceanfront Condo with Double Balconies & Marina Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Castaway Key, your perfect Florida Keys escape! Nestled between Key Largo and Islamorada, this bright and air ...
From $504 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Roosters Perch in Truman Annex, Porter Lane! This spacious corner duplex is flooded with natural light and b ...
From $268 per night (USD)
VRBO
From $585 per night (USD)
Expedia
333 Mariners Club - 3 bedroom condo with panoramic ocean views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Mariners Club Resort and Marina is one of the finest condominium properties in all of The Florida Keys. A gated, oceanfr ...
From $585 per night (USD)
Expedia
From $437 per night (USD)
VRBO
2306 Ocean Pointe Suites - Quality Decor with Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Well-appointed and updated, this lovely 2-bedroom oceanview condo in Ocean Pointe Resort is a delight! Located on the 3 ...
From $437 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Sept. spec @ 125 night lodg. With 4 night stay 4th night lodg. is FREE!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Close to beach, Full Kitchen and front porch. Very Reasonably Priced with 12% OFF Lodging + extras.WKLY stays ...
From $222 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Oceanside, Pet Friendly, Smart Home with-SUP, kayak with and 60 ft Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Great news, we just completed construction of a brand new 60FT dock. We have a kayak launch and plenty of room for your ...
From $290 per night (USD)
VRBO
From $433 per night (USD)
Expedia
305 Kawama Tower - 2 bedroom condo nicely furnished, comfy beds
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Clean and nicely decorated, this 3rd-floor condo exudes peace and harmony. Two-bedroom, two bath boasting 1300 sq ft o ...
From $433 per night (USD)
Expedia
From $1079 per night (USD)
VRBO
FL Keys Gulfside Waterfront Gated Home w/ Pool, Spa, Private Dock & Boat Ramp
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxury waterfront vacation rental property in Marathon Florida Keys with a private swimming pool, spa, dock, and boat ra ...
From $1079 per night (USD)
VRBO
From $720 per night (USD)
Expedia
812 Mariners Club - 4 bedroom townhome with comfortable open living area
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Bring the whole family and have room to spare! Over 2300 square feet await you in this corner townhouse with a thoughtfu ...
From $720 per night (USD)
Expedia
From $664 per night (USD)
VRBO
608 Mariners Club - Upscale 4 bedroom Tri-level Townhome, spacious luxury for the whole family
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Luxury tri-level townhouse located in the upscale Mariners Club Resort, a welcoming and tranquil community designed to p ...
From $664 per night (USD)
VRBO
From $785 per night (USD)
Expedia
The Gideon Lowe House - Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegance. Sophistication. Perfection. Welcome to the Gideon Lowe House, a historic treasure in the heart of Old Town Ke ...
From $785 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Keys to Paradise – Your Cozy Retreat in the Heart of Key West! Located in the charming Shipyard Condominium ...
From $295 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Discounted 3 to 6 months rentals. Plan your perfect getaways to paradise. 1/1 Fully Renovated Beautifully Designed Condo ...
From $250 per night (USD)
Expedia
From $1082 per night (USD)
VRBO
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1082 per night (USD)
VRBO
From $723 per night (USD)
Expedia
Exquisite Oceanfront Townhome!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This fully updated, two story townhome has 3 bedrooms and 3 bathrooms. Beautiful ocean views from the second floor balco ...
From $723 per night (USD)
Expedia
From $310 per night (USD)
VRBO
Key Largo 3 Bedroom Penthouse Condo with Boat Slip and Bay View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy your vacation in this unique 1580 square foot Penthouse Suite with all the amenities of home. Your suite is a rare ...
From $310 per night (USD)
VRBO
From $791 per night (USD)
Expedia
Beach Dream House, relax and enjoy the clear waters of Islamorada FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun risi ...
From $791 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Oceanfront 2BR Condo w/ Ocean Views Pool, Balcony – Near Key Largo/Islamorada!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ideally located midway between Key Largo and Islamorada you'll find our beautiful 2-bedroom condo that showcases the bes ...
From $220 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
House A - You're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a fe ...
From $401 per night (USD)
Expedia
From $917 per night (USD)
VRBO
Modern Waterfront Luxury Home with Heated Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...
From $917 per night (USD)
VRBO
From $886 per night (USD)
Expedia
Conch style home in Oldtown with private pool AND dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $886 per night (USD)
Expedia
From $966 per night (USD)
VRBO
Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $966 per night (USD)
VRBO
From $724 per night (USD)
Expedia
405 Mariners Club - 3 bedroom tri-level townhome with view of the oasis pool and the ocean
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Wake up to this idyllic view over the oasis pool out to the Atlantic Ocean...close your eyes and just breathe.... whethe ...
From $724 per night (USD)
Expedia
From $904 per night (USD)
VRBO
Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Grouper House — Your Private Ultra Luxury Retreat in the Heart of the Florida Keys Step into Grouper House, ...
From $904 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Florida Keys Townhouse For Rent 2/2
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in Kawama Yacht Club, a secure gated community with a peaceful island feeling. Our townhouse was renovated 6 mon ...
From $268 per night (USD)
Expedia
From $344 per night (USD)
VRBO
BEST Ocean Views All Rooms Building 4, 4th floor! Largest - End Unit, Quiet !!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We received VRBO’s and AIRBNB’s Super-Host Certificate of Excellence "Best Condo in the Keys" awards! Its all about bei ...
From $344 per night (USD)
VRBO
From $571 per night (USD)
Expedia
Sunset Catch- Gulf Front, Open Water Views, Private Pool and Dock, Kayaks.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Whether an avid adventurer or a family seeking to relax and enjoy the expansive view, Sunset Catch is the place for you. ...
From $571 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Sept [email protected] + With 4 night stay 4th night FREE lodging!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Outdoor patio, Full kitchen and Close to the beach🌴🍹🐠 WKLY SPECIALS @ 12% OFF Wkly & REDUCED RATES This is a ...
From $211 per night (USD)
VRBO
From $1426 per night (USD)
Expedia
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $1426 per night (USD)
Expedia
From $142 per night (USD)
VRBO
SUNSET BEACH APARTMENT
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
<p>Nestled in Key Largo, this 1-bedroom, 1-bathroom vacation home brings it all within your reach. Fans of nature and th ...
From $142 per night (USD)
VRBO
From $919 per night (USD)
Expedia
New! Oceanfront Showhouse Casa Mar • NO HIDDEN FEES! Pools • Hot Tubs • 2 Kings
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
No Hidden Fees! Book any of my homes with confidence. Unlike many vacation rentals, I don't add resort, guest, or manage ...
From $919 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Beautiful 2/2 Waterfront Designer Home for your family vacation
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our backyard will be under construction for the summer of 2026 so as to add in a pool, spa, and Tiki with landscaping. P ...
From $206 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Relax and unwind in this spacious 1,200 sq ft waterfront condo in downtown Key West. Perfect for families and ...
From $368 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Waterfront Condo + Pool Downtown + Boat Slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Experience spacious waterfront living in Key West in this bright 2-bed, 2-bath condo overlooking a marina in D ...
From $364 per night (USD)
VRBO
From $912 per night (USD)
Expedia
Penthouse Waterfront Dock Pool Condo Near Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring the whole crew to this spacious 2,200 sq ft waterfront penthouse in downtown Key West, perfect for famil ...
From $912 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Waterfront Dock Pool Key West Near Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Relax in this bright 2nd-floor corner waterfront condo in downtown Key West, offering extra natural light and ...
From $400 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $186 per night (USD)
Expedia
From $300 per night (USD)
VRBO
W16 - 3 bed, 2 bath Tropical Bungalow with Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This adorable 3 bedroom, 2 bath waterfront home provides an exclusive retreat from the hustle and bustle of everyday lif ...
From $300 per night (USD)
VRBO
From $300 per night (USD)
Expedia
W15 - 3 bed, 2 bath Caribbean Bungalow with Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This adorable 3 bedroom, 2 bath waterfront home provides an exclusive retreat from the hustle and bustle of everyday lif ...
From $300 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Stunning home on the canal with boat dock exclusive Key Colony Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully appointed home on 7th St with the widest canal in KCB. Located across the street from a children's park, dog ...
From $335 per night (USD)
VRBO
From $311 per night (USD)
Expedia
C14 Moon Bay - Recently renovated 2 bedroom townhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Park right in front of your townhouse! The ground-level front entrance takes you into the casual dining area and seatin ...
From $311 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $398 per night (USD)
VRBO
From $281 per night (USD)
VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $281 per night (USD)
VRBO
From $398 per night (USD)
VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $398 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Island Luxury, Upscale, Walk to Sombrero Beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
The physical address is 90 Calle Ensueno, Marathon FL 33050 Come stay, fish, snorkel, relax in the pool, walk to Sombre ...
From $955 per night (USD)
Expedia

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