Florida Keys Rentals
From $1108 per night (USD)VRBO
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)VRBO
From $233 per night (USD)Expedia
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)Expedia
From $365 per night (USD)VRBO
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)VRBO
From $724 per night (USD)Expedia
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)Expedia
From $409 per night (USD)VRBO
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)VRBO
From $546 per night (USD)Expedia
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)Expedia
From $381 per night (USD)VRBO
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)VRBO
From $214 per night (USD)Expedia
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)Expedia
From $399 per night (USD)VRBO
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)VRBO
From $933 per night (USD)Expedia
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)Expedia
From $733 per night (USD)VRBO
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)VRBO
From $472 per night (USD)Expedia
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)Expedia
From $280 per night (USD)VRBO
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)VRBO
From $817 per night (USD)Expedia
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)Expedia
From $285 per night (USD)VRBO
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)VRBO
From $652 per night (USD)Expedia
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)Expedia
From $259 per night (USD)VRBO
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)VRBO
From $794 per night (USD)Expedia
**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)Expedia
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)Expedia
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)Expedia
From $224 per night (USD)VRBO
**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)VRBO
From $368 per night (USD)Expedia
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)Expedia
From $394 per night (USD)VRBO
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)VRBO
From $543 per night (USD)Expedia
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)Expedia
From $347 per night (USD)VRBO
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)VRBO
From $344 per night (USD)Expedia
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)Expedia
From $901 per night (USD)VRBO
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)VRBO
From $469 per night (USD)Expedia
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)Expedia
From $504 per night (USD)VRBO
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)VRBO
From $268 per night (USD)Expedia
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)Expedia
From $585 per night (USD)VRBO
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)VRBO
From $437 per night (USD)Expedia
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)Expedia
From $222 per night (USD)VRBO
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)VRBO
From $290 per night (USD)Expedia
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)Expedia
From $433 per night (USD)VRBO
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)VRBO
From $1079 per night (USD)Expedia
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)Expedia
From $720 per night (USD)VRBO
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)VRBO
From $664 per night (USD)Expedia
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)Expedia
From $785 per night (USD)VRBO
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)VRBO
From $295 per night (USD)Expedia
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)Expedia
From $250 per night (USD)VRBO
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)VRBO
From $1082 per night (USD)Expedia
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)Expedia
From $723 per night (USD)VRBO
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)VRBO
From $310 per night (USD)Expedia
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)Expedia
From $791 per night (USD)VRBO
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)VRBO
From $220 per night (USD)Expedia
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)Expedia
From $401 per night (USD)VRBO
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)VRBO
From $917 per night (USD)Expedia
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)Expedia
From $886 per night (USD)VRBO
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)VRBO
From $966 per night (USD)Expedia
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)Expedia
From $724 per night (USD)VRBO
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)VRBO
From $904 per night (USD)Expedia
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)Expedia
From $268 per night (USD)VRBO
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)VRBO
From $344 per night (USD)Expedia
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)Expedia
From $571 per night (USD)VRBO
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)VRBO
From $211 per night (USD)Expedia
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)Expedia
From $1426 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
From $206 per night (USD)Expedia
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)Expedia
From $368 per night (USD)VRBO
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)VRBO
From $364 per night (USD)Expedia
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)Expedia
From $912 per night (USD)VRBO
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)VRBO
From $400 per night (USD)Expedia
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)Expedia
From $186 per night (USD)VRBO
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)VRBO
From $300 per night (USD)Expedia
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)Expedia
From $300 per night (USD)VRBO
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)VRBO
From $335 per night (USD)Expedia
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)Expedia
From $311 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
From $1077 per night (USD)Expedia
World class ocean views on a sugar sand beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful home located right on the ocean and sits on a sugar sand beach. Truly, world class views from all 3 levels. ...
From $1077 per night (USD)Expedia
From $550 per night (USD)VRBO
Florida Keys, private wellness enjoyment with private hot tub and plunge pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Property features a private hot tub, private plunge pool and a shared pool and many more amenities to make your vacation ...
From $550 per night (USD)VRBO
From $311 per night (USD)Expedia
B405 Moon Bay - Inviting Waterfront Condo with Breathtaking Sunsets
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
From sunrise to sunset, you can enjoy the many activities that Moon Bay condominium has to offer! The condo itself has ...
From $311 per night (USD)Expedia
From $6223 per night (USD)VRBO
Ocean Panorama w private pool, huge yard, fire pit, kayaks, SUPs
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spectacular 4 bedroom, 3 bath oceanfront bungalow estate. Perfect for family, sports, nature and relaxation. Availab ...
From $6223 per night (USD)VRBO
From $526 per night (USD)Expedia
Emerald Seas - Florida Keys Ocean Front Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal ...
From $526 per night (USD)Expedia
From $427 per night (USD)VRBO
Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $427 per night (USD)VRBO
From $648 per night (USD)Expedia
The Flight Deck - 3 Bedroom / 3 Bathroom with Shared Pool & Fitness Center!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to “The Flight Deck” — Your Tropical Getaway in Key West Location: Coral Hammock Community, Stock Island – Just ...
From $648 per night (USD)Expedia
From $927 per night (USD)VRBO
Salty Kisses Beach House
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Salty kisses are a Modern brand-new construction 5/4 beach house with a pool and a dock. Salty kisses is a piece of par ...
From $927 per night (USD)VRBO
From $709 per night (USD)VRBO
Ideal Family Stay in Great Location, 4 Pools, Shuttle Service, Near Airport!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $709 per night (USD)VRBO
From $389 per night (USD)VRBO
Beautiful Water Views! Minutes to Southernmost Point! Parking, Onsite Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $389 per night (USD)VRBO
From $754 per night (USD)VRBO
Canalfront 4-Bedroom Mangrove Sunset in Islamorada with dockage and 2 boat lifts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning pool home is nestled along a private canal with convenient dockage and quick access to the bay! This lu ...
From $754 per night (USD)VRBO
From $818 per night (USD)VRBO
Key Largo Home 3 Bed/3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful place to stay! MAGNIFICENT KEY LARGO BAYVIEW HOME. This luxurious 3 Bedroom ...
From $818 per night (USD)VRBO
From $1482 per night (USD)Expedia
Complete Duplex on Gated Bayfront Property
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
PROPERTY NAME: Little Bay Prime 82246 Overseas Highway, Islamorada, Florida LOCATION: Two story Duplex Located Directl ...
From $1482 per night (USD)Expedia
From $738 per night (USD)VRBO
2nd Floor Duplex on Gated Bayfront Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROPERTY NAME: Little Bay Upper Duplex 82246 Overseas Highway, Islamorada, Florida LOCATION: Upper Duplex located direc ...
From $738 per night (USD)VRBO
From $2196 per night (USD)Expedia
Entire Compound on Gated Bayfront Property
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
PROPERTY NAME: Little Bay Compound 82246 Overseas Highway, Islamorada, Florida LOCATION: Cottage and Two Story Duplex ...
From $2196 per night (USD)Expedia
From $739 per night (USD)VRBO
Gated Estate Duplex on the Bay with dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
PROPERTY NAME: Little Bay Lower Duplex 82246 Overseas Highway, Islamorada, Florida LOCATION: Duplex located directly on ...
From $739 per night (USD)VRBO
From $1833 per night (USD)Expedia
Key Largo 4BR Villa – Partial Ocean View & Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Coral Breeze #46 4 Bed 4.5 Bath Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace an ...
From $1833 per night (USD)Expedia
From $1833 per night (USD)VRBO
Key Largo 4BR Villa | Partial Ocean View + Marriott
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Coastal Oasis #44 4 Bed 4.5 Bath Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace ...
From $1833 per night (USD)VRBO
From $1283 per night (USD)Expedia
Villa in Key Largo – Pool & Beach Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Sea-Esta #25 (3 Bed / 2.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace an ...
From $1283 per night (USD)Expedia
From $1621 per night (USD)VRBO
Key Largo 4BR Villa | Pool, Clubhouse & Gym
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Twilight #32 (4Bed / 4.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace and ...
From $1621 per night (USD)VRBO
From $1621 per night (USD)Expedia
Key Largo 4BR Villa | Pool + Resort Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Latitudes #34 (4Bed / 4.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace an ...
From $1621 per night (USD)Expedia
From $1833 per night (USD)VRBO
Full Ocean View Luxury Villa | Gym & Beach Club
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Lookout #48 (4Bed / 4.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace ...
From $1833 per night (USD)VRBO
From $1621 per night (USD)Expedia
4BR Villa w/ Private Pool & Gym Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Sea Haven #38 (4Bed / 4.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace an ...
From $1621 per night (USD)Expedia
From $1620 per night (USD)VRBO
Villa in Key Largo – Gym, Pool + Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Sandcastle 4 Bed 4.5 Bath | 3888 SF | 3-Story Home | Multi Terrace | Indulge in a tranquil, carefully crafted vacation r ...
From $1620 per night (USD)VRBO
From $602 per night (USD)Expedia
Happy Tingler With Pool Tiki and 100 ft of Dockage Right Next to Sombrero Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Vaca-23-297 Dreaming of the beach? Look no further located in the small subdivision just a couple of blocks from Somb ...
From $602 per night (USD)Expedia
From $527 per night (USD)VRBO
**MODERN MAJESTY @ THE ANNEX** Condo & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN MAJEST ...
From $527 per night (USD)VRBO
From $307 per night (USD)Expedia
Bayside Condo with Pool and Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly updated, beachy inspired, 2 bedroom, 2 bathroom condo next to pool and marina. Unit comes complete with all the a ...
From $307 per night (USD)Expedia