Florida Keys Rentals
- From $250 per night (USD)
VRBO
P36 - Charming and immaculate 2 Bedroom, 2 bathroom stilted, half duplex with...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Charming and immaculate 2 Bedroom, 2 bathroom stilted, half duplex offering deep-water dockage and private pool. Located ...
From $250 per night (USD)VRBO
- From $344 per night (USD)
Expedia
Midnight Cowboy by AvantStay | 3 Artistic Spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
*Please note that this home is available for 28+ night stays only.* Midnight Cowboy is a one-of-a-kind Key West escape ...
From $344 per night (USD)Expedia
- From $147 per night (USD)
VRBO
Monkey House by AvantStay | Pool, by Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Monkey House is a two-bedroom Key West escape that ...
From $147 per night (USD)VRBO
- From $156 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $156 per night (USD)Expedia
- Click For Pricing
VRBO
Bogie Channel House - Adorable home with easy access to the Gulf or Ocean.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This adorable home located on Big Pine Key has easy boating access to the Gulf and Ocean. Bring your boat or rent one f ...
Click For PricingVRBO
- From $299 per night (USD)
Expedia
Speakeasy Inn - 1C (1 Queen Bed & Sleeper Sofa)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $299 per night (USD)Expedia
- From $289 per night (USD)
VRBO
Speakeasy Inn - Room 1A (1 Queen Bed & 1 Single Sleeper Sofa)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $289 per night (USD)VRBO
- From $135 per night (USD)
VRBO
Little piece of Paradise in Key Largo!! \nThat you will absolutely love!!\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cozy 2-bedroom, 1-bath home invites you to experience the stunning Key Largo weather and its picturesque surroundin ...
From $135 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful Waterfront Townhome in Islamorada with Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Cozily furnished bayside townhome & boat slip (option to rent), located in desirable 'Futura Yacht Club' gated community ...
Click For PricingVRBO
- From $360 per night (USD)
VRBO
Rum Cay\/ 2 bedroom 2 bath Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rum Cay offers a quiet alternative to the downtown area of Key West. Located a short 10-minute ride away from the nightl ...
From $360 per night (USD)VRBO
- From $498 per night (USD)
VRBO
Sale! Bayfront, Private Pool Home, 110’ Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Turtle Cove Escape: located on Marathon is a 3 bedroom 2 bath single family Private House, Private Pool 3 Bedrooms 2 ful ...
From $498 per night (USD)VRBO
- From $511 per night (USD)
Expedia
Sale! Game Room, Priv Hot Tub, Dock, Tiki Hut!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
* Pool & Tiki are expected to be completed by Summer 2024! Experience the ultimate “keezy” getaway at "Sea You Soon". Th ...
From $511 per night (USD)Expedia
- From $158 per night (USD)
VRBO
Oceanfront Gated Community \/ Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Oceanfront Luxury gated townhome community on seven acres. Resort amenities include large elevated pool with fabulous oc ...
From $158 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Ocean Front Condo in Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a recently renovated 2 bedroom, 2 bathroom, oceanfront condo. It is bright, cheerful and has an tropical beach t ...
From $350 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Mid-FL Keys Coco Plum Penthouse-Ocean View 1Bd LRG heated pool semi-Lux Reno #35
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Newly Listed-OCT 2023. Middle Keys Coco Plum Area of Marathon, FL. Semi-Luxurious "Coco Plum Penthouse" w/Ocean View. 2 ...
From $324 per night (USD)VRBO
- From $375 per night (USD)
Expedia
1st year for this gorgeous 4Bd 4Ba all ensuite, 2 parking spots, backyard oasis!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Moveable Feast, a new monthly vacation rental in the heart of Bahama Village that sleeps 10 comfortably. Loca ...
From $375 per night (USD)Expedia
- From $139 per night (USD)
VRBO
Old Town Key West Home w\/ Deck < 1 Mi to Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ensure your next stop in Key West includes easy access to all of the island’s most iconic attractions when you book this ...
From $139 per night (USD)VRBO
- From $441 per night (USD)
Expedia
Luxury 62' Yacht! In a Beautiful Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
You and your guests will have exclusive use of this 62 ft yacht all to yourselves. The yacht stays docked, the entire re ...
From $441 per night (USD)Expedia
- From $595 per night (USD)
VRBO
KAMP by Brightwild | Rooftop Penthouse On Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $595 per night (USD)VRBO
- Click For Pricing
Expedia
Tranquility in Tavernier FL: House in Upper Keys - space for RV, boat, trailer.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Fully furnished single family home with coastal design, featuring 2 bedrooms, 2 full baths, and a balcony that opens fro ...
Click For PricingExpedia
- From $395 per night (USD)
VRBO
Beautiful condo at a great location in Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This recently remodeled and upgraded 2 bedroom, 2 bathroom, Ocean Front Condo with a balcony has a view of the park and ...
From $395 per night (USD)VRBO
- From $219 per night (USD)
Expedia
Dolphin Cove~Stunning townhome in beautiful Bonefish Yacht Club- 2 Paddleboards!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Dolphin Cove! Nestled in the heart of the picturesque Bonefish Yacht Club, this vacation rental offers the p ...
From $219 per night (USD)Expedia
- From $304 per night (USD)
VRBO
Waterfront home with private pool, bar\/grill, screened patio, & boat access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Waypoint One Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $304 per night (USD)VRBO
- From $161 per night (USD)
Expedia
Little Venice Family Affair 2 bedroom 1 bath One Block from the Ocean
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cute as a button adorable Conch Cottage in the heart of Marathon, and only a block from the ocean. The ocean breeze is l ...
From $161 per night (USD)Expedia
- From $310 per night (USD)
VRBO
Charming Home in Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Lovely Keys Home located in a quiet residential neighborhood on the bay side. The house is on the 1st floor with a large ...
From $310 per night (USD)VRBO
- From $107 per night (USD)
Expedia
Capt Craig's 1 Bedroom \/1 Bath Apartment in Islamorada, Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Capt. Craig’s Guest Quarters -The Seahorse is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami Inter ...
From $107 per night (USD)Expedia
- From $456 per night (USD)
VRBO
Romantic Retreat - 2 person K Suite, Pvt deck\/Spa!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottage ...
From $456 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Large Family Home- Sleeps 12 w\/Direct Ocean Axcess on Canal
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Escape to Marathon is a Large 5 Bedroom Home. This is our second home, we make sure it is clean and fun. We Constantly d ...
From $700 per night (USD)VRBO
- From $238 per night (USD)
VRBO
Waterfront House with Dockage and Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a 2 bedroom, 1 bathroom waterfront 1st floor of a 2 story house that is 200 feet from the Atlantic Ocean. It ...
From $238 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Waterfront Ground Level House in Key Largo with Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This bright, beautiful, spacious, impeccably decorated 2 bedroom, 2 bathroom waterfront house in Tavernier is located in ...
From $254 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Key West Lighthouse Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Key West Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suites Collection, is a 5-star, 1 ...
From $425 per night (USD)VRBO
- From $425 per night (USD)
VRBO
American Shoal Suite | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unexpected Location The American Shoal Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suites ...
From $425 per night (USD)VRBO
- From $369 per night (USD)
VRBO
Tortugas Harbor Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Unexpected Location The Tortugas Harbor Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suite ...
From $369 per night (USD)VRBO
- From $214 per night (USD)
Expedia
Lower Keys on quiet canal front w\/boat lift, screened-in porch & Pets Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your own relaxing quiet oasis. Fenced in yard that offers privacy with the foliage beyond the banana palms an ...
From $214 per night (USD)Expedia
- From $284 per night (USD)
VRBO
L` Attitude Adjustment Monthly Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Dream Getaway in Key West, Florida! Discover the ultimate monthly vacation rental in Key West. This stun ...
From $284 per night (USD)VRBO
- Click For Pricing
VRBO
2 Family-friendly Units, Onsite Pool, Tennis Court, Steps Away from the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Indulge in the array of fantastic amenities available to our guests. Dive into our sparkling pool and let the cool water ...
Click For PricingVRBO
- From $1128 per night (USD)
VRBO
3 Units with Ocean View, Full Kitchens, Perfect for Groups! Outdoor Pool!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Indulge in the array of fantastic amenities available to our guests. Dive into our sparkling pool and let the cool water ...
From $1128 per night (USD)VRBO
- Click For Pricing
VRBO
3 Family-friendly Units, Onsite Pool, Tennis Court, Steps Away from the Beach!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Indulge in the array of fantastic amenities available to our guests. Dive into our sparkling pool and let the cool water ...
Click For PricingVRBO
- From $895 per night (USD)
VRBO
Steps Away from the Beach! 3 Spacious Units, Full Kitchens, Outdoor Pool!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Indulge in the array of fantastic amenities available to our guests. Dive into our sparkling pool and let the cool water ...
From $895 per night (USD)VRBO
- From $751 per night (USD)
VRBO
Perfect for Groups! 2 Units with Ocean View, Full Kitchens, Outdoor Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Indulge in the array of fantastic amenities available to our guests. Dive into our sparkling pool and let the cool water ...
From $751 per night (USD)VRBO
- From $633 per night (USD)
VRBO
Steps Away from the Beach! 2 Spacious Units, Full Kitchens, Outdoor Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Indulge in the array of fantastic amenities available to our guests. Dive into our sparkling pool and let the cool water ...
From $633 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Sombrero Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Unexpected Location The Sombrero Reef Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suites ...
From $405 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Alligator Reef Suite | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Alligator Reef Suite, a beautiful 2 bedroom vacation rental property located just half a block from Duval ...
From $425 per night (USD)VRBO
- From $765 per night (USD)
Expedia
Just renovated in 2023 Spacious 3 Bedroom, 4 Balcony Waterfront Townhouse
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
3 Bedrooms + Den, 3 Bathrooms, 4 Balconies, Lagoon Front Townhouse, in Key Largo, which sleeps up to 8. It was completel ...
From $765 per night (USD)Expedia
- From $919 per night (USD)
VRBO
~CALIFORNIA DREAMING~ Enjoy an extended vacation in this posh home and pool.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $919 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Stunning Oceanfront Keys Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 1,200-square foot home is a gorgeous ocean front property just minutes from back country and oceanside fishing. Tuc ...
From $295 per night (USD)Expedia
- Click For Pricing
Expedia
Florida Keys, Sun, Sea, Fishing, Restaurants and Sightseeing Vacations
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the morning sunrise along side a panoramic view of the marina and ocean from the large patio or 2nd floor balcony ...
Click For PricingExpedia
- From $624 per night (USD)
Expedia
Custom House Inn | Two 2nd Floor Suites On Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $624 per night (USD)Expedia
- From $605 per night (USD)
VRBO
Custom House Inn | Two Suites On Duval St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $605 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Spectacular newly remodeled condo in the Florida Keys.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully and totally remodeled spacious condo with an amazing view of the Florida Bay, Key Largo. This 2nd floor unit ...
From $375 per night (USD)Expedia
- From $213 per night (USD)
VRBO
If you like warm weather, sunshine, and the ocean, this is the place to be!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Marathon home in a quiet neighborhood. Near beaches, boat ramp, water sports, fishing, snorkeling, resteraunts and shops ...
From $213 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Escape to Serenity: Luxurious Waterfront Villa - Your Ultimate Vacation Retreat!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to our stunning waterfront villa in Marathon, Florida, where the true heart of the home lies in its captivating ...
From $650 per night (USD)Expedia
- From $415 per night (USD)
VRBO
Blue Lagoon Paradise Point \nRare point house with 230 ft surrounded by water …
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
If you’re looking for a coastal experience with a modern peaceful clean stay this home is for you. Stay comfortably in S ...
From $415 per night (USD)VRBO
- From $492 per night (USD)
Expedia
Stay Anchored at Sombrero - Book Your Ultimate Escape to Paradise in Marathon
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Embark on an idyllic getaway to our spacious 4-bedroom, 3-bathroom vacation home nestled in Marathon, the heart of the F ...
From $492 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Delancey Hall in Old Town with a pool and privacy!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local and walk or bike to town. Enjoy your large furnished front porch or your own private back porch by the ...
From $500 per night (USD)VRBO
- From $206 per night (USD)
Expedia
Brand New Home, Resort Location, Oceanview
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full ...
From $206 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Studio Unit in quiet resort adjacent to Old Town Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
From $250 per night (USD)VRBO
- From $680 per night (USD)
Expedia
Conch Cottage located minutes from Sombrero Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Conch Cottage! Nestled in the welcoming Sombrero Beach neighborhood just moments away from the pristine s ...
From $680 per night (USD)Expedia
- From $290 per night (USD)
VRBO
Beautiful Home in Marathon, In the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Water views from main area, and b ...
From $290 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
Spectacular 4 bedroom 4 1\/2 bath villa on Tavernier Creek in Florida Keys.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Incomparable villa directly on Tavernier Creek with immediate access to ocean and bay. Fully fenced and gated. Manatees ...
From $1000 per night (USD)Expedia
- From $206 per night (USD)
VRBO
Brand New Home, Resort Location, Oceanview
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full ...
From $206 per night (USD)VRBO
- From $230 per night (USD)
VRBO
BEAUTIFUL PLACE TO STAY!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
ONE OF "THE BEST" vacation value getaways in the Florida Keys. Packed with amenities, it has access to gulf side docka ...
From $230 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Ocean Harbor Paradise is Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Talk about an Atlantic Ocean View; you've found it! You will fall in love as soon as you enter the gates at Ocean Harbor ...
From $300 per night (USD)VRBO
- From $356 per night (USD)
Expedia
Discover paradise in this bay view tropical oasis for the perfect Keys gateway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The space We want to go above and beyond to provide an amazing stress-free vacation and experience that accommodates to ...
From $356 per night (USD)Expedia
- From $375 per night (USD)
VRBO
NEW! Atlantic Oasis | Heated Pool, Near Beach!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Atlantic Oasis is a true Key West "Conch Style" townhome consisting of over 1900 sq. ft. of beautiful living sp ...
From $375 per night (USD)VRBO
- From $175 per night (USD)
Expedia
The Bent Anchor-boat lift diving snorkeling fishing key deer 22 miles Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our 3 bedroom, 2 full bath home on canal front Ramrod key. Quite laidback community. Great fishing & diving. ...
From $175 per night (USD)Expedia
- From $235 per night (USD)
VRBO
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer\/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $235 per night (USD)VRBO
- From $237 per night (USD)
Expedia
Waterfront Home with 33-Ft. Dock and Cabana Club Membership with Beach and Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Ninth Street Cabana Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $237 per night (USD)Expedia
- From $176 per night (USD)
VRBO
Waterfront home with private dock, canal views, large terrace & modern kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
La Isla Bonita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $176 per night (USD)VRBO
- From $600 per night (USD)
Expedia
Two Master Suites! 35' Boat Dockage! Outdoor Living Space & Summer Kitchen!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
At Sombrero Serenity boaters will appreciate the deep water docking out back with room to accommodate up to a 35 ft. boa ...
From $600 per night (USD)Expedia
- From $467 per night (USD)
VRBO
W04 - 209 Sombrero Beach Rd.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newer built canal front townhouse in the Anglers area of the Sombrero Beach neighborhood. This home features a private h ...
From $467 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Keys Cottage with Beach and Dockage! Bayfront Property!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
"Deckhouse" is the perfect beachy cottage for your Keys vacation! It has a full-size kitchen with granite countertops an ...
From $350 per night (USD)VRBO
- From $147 per night (USD)
VRBO
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
water front home is located on 100 foot wide canal with your own 30 feet of Free dockage. We are pet friendly. Furnished ...
From $147 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always ...
From $275 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Waterfront Cottage - Beach and Dockage! Open Water Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
In a world of chain hotels and paved over paradise, experience the Florida Keys the way they used to be! Sitting on a pr ...
From $350 per night (USD)VRBO
- From $371 per night (USD)
Expedia
\"Your own private resort\" - Mockingbird Pointe - Waterfront, pool and dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with priva ...
From $371 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Nader's Vacation Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We have our 3 bedroom 2 bathroom home in Little Torch Key available for anyone looking to take a vacation in the lower ...
From $200 per night (USD)VRBO
- From $321 per night (USD)
Expedia
P64 - Spacious 3 bedroom duplex in Key Colony with dockage and Cabana Club...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $321 per night (USD)Expedia
- From $95 per night (USD)
VRBO
Great Rates! Remodeled Cozy Waterfront Mobile Home In Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Totally remodeled home located at Eagle Dr in quiet Sexton Cove. 5 minutes away from John Pennekamp State Park, great r ...
From $95 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, ...
From $225 per night (USD)Expedia
- From $634 per night (USD)
VRBO
A Taste Of Vitamin Sea 4bed\/3bath updated single family with pool, dockage &
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
STR21-000361 Your vacation awaits at A Taste of Vitamin Sea in desirable Key Colony Beach! Vitamin Sea’s canal fronta ...
From $634 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and bea ...
From $300 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Elegant Home with Beach & Dockage! Spectacular Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This elegant home, with many unique, architectural features, is located on a beautiful waterfront piece of property, wit ...
From $700 per night (USD)VRBO
- From $310 per night (USD)
Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $310 per night (USD)Expedia
- From $1948 per night (USD)
VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $1948 per night (USD)VRBO
- From $517 per night (USD)
Expedia
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Anchor House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $517 per night (USD)Expedia
- From $527 per night (USD)
VRBO
3BR\/3BA Sunset Cottage located at The Villages of Hawks Cay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
In response to COVID-19, our cottage will be disinfected and sanitized professionally prior to all check-ins. Professio ...
From $527 per night (USD)VRBO
- From $460 per night (USD)
Expedia
Henry's Penthouse on the Ocean in Key West (weekly \/ nightly rentals)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $460 per night (USD)Expedia
- From $590 per night (USD)
VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $590 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Key Largo! Luxurious 2BR\/2BA! Amazing Pool and Large Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning Condo with Garden View located in Tavernier, Key Largo, Florida. Escape to paradise in this breathtak ...
From $242 per night (USD)Expedia
- From $311 per night (USD)
VRBO
Spectacular Open-Water Sunset Views with Boat Slip & Trailer Parking.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful newly refreshed vacation rental is all about the view. It is upstairs with an unobstructed view of the Fl ...
From $311 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Canal-front home remodeled for HGTV with private swimming pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
La Pirata Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $321 per night (USD)Expedia
- From $287 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $287 per night (USD)VRBO
- From $401 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $401 per night (USD)Expedia
- From $499 per night (USD)
VRBO
Waterfront Duck Key Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy Duck Key in the Florida Keys, known as America's Caribbean, a lush shangri-la with tropical vegetation an ...
From $499 per night (USD)VRBO
- From $210 per night (USD)
Expedia
Vacation like a local
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
From $210 per night (USD)Expedia
- From $329 per night (USD)
VRBO
COCONUT Adorable cottage in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $329 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Ocean Shores Lux-Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanside single family home in one of Key largo most desirable neighborhoods with waterview and private pool. Large lot ...
From $199 per night (USD)Expedia
- From $235 per night (USD)
VRBO
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $235 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We are so proud to say our tropical Bungalow now has 72 Straight 5 STAR REVIEWS on VRBO What sets us apart from "just ...
From $575 per night (USD)Expedia