Florida Keys Rentals
From $868 per night (USD)VRBO
4 Bed 5 Bath 75ftDock DeepWater Canal Private SaltWater Heated Pool Kayaks Bikes
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Luxury at its BEST! Whether its Dining Fishing Sunning or Shopping that floats your boat you can "Expect the BEST and t ...
From $868 per night (USD)VRBO
From $289 per night (USD)Expedia
Speakeasy Inn -Room 1B-1 Queen Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
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)Expedia
From $400 per night (USD)VRBO
Large Estate Modern Home on The Water with Great Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
LARGE 4 BEDROOMS 3 BATHROOMS IN KEY LARGO ON THE WATER, MODERN HOME ALL GATED, ELECTRIC GATE, EV READY, 4 STORY HOME WIT ...
From $400 per night (USD)VRBO
From $343 per night (USD)Expedia
Largo Sound Casita Su
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: *NEW Listing* This is a 2 story building right next to John Pennekamp Coral Reef State Park. Beautiful water vi ...
From $343 per night (USD)Expedia
From $400 per night (USD)VRBO
Large Estate Modern Home on The Water with Great Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
LARGE 4 BEDROOMS 3 BATHROOMS HOME IN KEY LARGO ON THE WATER, MODERN HOME ALL GATED, ELECTRIC GATE, EV READY, TWO MASTER ...
From $400 per night (USD)VRBO
From $461 per night (USD)VRBO
Starr's Suite - 2 person K Suite w\/Private Spa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, ...
From $461 per night (USD)VRBO
From $175 per night (USD)VRBO
**KESTRAL KOVE @ THE GOLF CLUB** Townhome w\/ Community Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of va ...
From $175 per night (USD)VRBO
From $1752 per night (USD)Expedia
Bumpa's Big House - Bring the Grandkids!
- Bedrooms:
- 13
- Bathrooms:
- 10
- Sleeps:
- 22
Escape to the epitome of luxury at Bumpa's Big House. This exquisite retreat accommodates gatherings of up to 22 guests, ...
From $1752 per night (USD)Expedia
From $300 per night (USD)VRBO
FISHERMANS DREAM HOUSE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bring your boats to this amazing house with 180ft. of seawall secluded on a corner lot. Boat ramp minutes away. Ice make ...
From $300 per night (USD)VRBO
From $346 per night (USD)Expedia
Dolphin Retreat-3 bedroom 2 Bath Marathon Home w Private Pool & 60 foot Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Have you been dreaming of a sun-soaked Florida Keys getaway with ample space for your whole family? Turn those dreams in ...
From $346 per night (USD)Expedia
From $275 per night (USD)VRBO
Bimini Breeze in Cudjoe Key
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your dream vacation destination! This beautifully updated and remodeled 2-bedroom, 1-bathroom rental property ...
From $275 per night (USD)VRBO
From $299 per night (USD)Expedia
The Speakeasy Inn - Room 1A (1 Queen Bed & 1 Single Bed)
- 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 $299 per night (USD)Expedia
From $299 per night (USD)VRBO
Room 2 (1 Queen Bed & 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 $299 per night (USD)VRBO
From $300 per night (USD)Expedia
Private & Haven-ly pool home on boating canal
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
About this space This Haven-ly Marina home is a picture perfect Keys escape. The 2 bed/2 bath main home and 1/1 casita i ...
From $300 per night (USD)Expedia
From $325 per night (USD)VRBO
Southern Skies, Stylish Home in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart ...
From $325 per night (USD)VRBO
From $139 per night (USD)Expedia
Breezy Key West 1st-Floor Condo w\/ Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $139 per night (USD)Expedia
From $304 per night (USD)VRBO
HotTub Hideaway! PoolTable& More
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome To Your HotTub Hideaway! PRIVATE, SECLUDED, INTIMATE AREA (JACUZZI, PUTT-PUTT, BBQ, CORNHOLE, PRIVATE BAR, POOL ...
From $304 per night (USD)VRBO
From $270 per night (USD)VRBO
Our Florida Keys \"Sea-Cove\"! Canal front, Boat dockage, Pool, Private!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Make our happy place, your happy place! Escape to this canal front retreat and leave your worries behind. This 2-bedr ...
From $270 per night (USD)VRBO
Click For PricingVRBO
Paradise Palace 3\/3 Waterfront Pool Kayak 70' Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Close to restaurants and dining, parks, and great views. You’ll love my home because of the peaceful atmosphere, sitting ...
Click For PricingVRBO
From $821 per night (USD)Expedia
Sandy Beach Cove🏝️🏖️ Private Beach Home and Cottage Compound with Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Relax , Enjoy and Indulge yourself with Family and friends on this Over Half Acre Private Ocean Beach Oasis 🏝️🏖️ with ...
From $821 per night (USD)Expedia
From $367 per night (USD)VRBO
Keys To The Kingdom! Private Oceanfront Retreat with Beach and Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
There's no better place to experience the magic of the Florida Keys than this bright and remodeled three-bedroom getaway ...
From $367 per night (USD)VRBO
From $156 per night (USD)Expedia
Radiant waterfront retreat with remarkable views, patio, tennis court, & grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tollgate Tides Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $156 per night (USD)Expedia
From $307 per night (USD)VRBO
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You and your guests will have exclusive use of this 45 ft yacht all to yourselves. The yacht stays docked, the entire re ...
From $307 per night (USD)VRBO
From $295 per night (USD)Expedia
Islamorada waterfront villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Resort Style Venetian Shores Home with 70 ft Dock on a 100 foot wide canal Completely remodeled. Two Bedrooms with King ...
From $295 per night (USD)Expedia
From $769 per night (USD)VRBO
Brand New Luxury 5 Bedroom Oceanfront Home w\/Pool, 38' Boat Slip, Prime Location
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Emerald Oasis, a premier retreat in the heart of the Florida Keys! Experience luxury and comfort in a brand- ...
From $769 per night (USD)VRBO
From $675 per night (USD)Expedia
Waterfront Captain House with Boat Basin & Ramp!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin for your boat. The property ...
From $675 per night (USD)Expedia
From $199 per night (USD)VRBO
Your Happy Place - gorgeous 2 bed 2 bath oceanfront suite with full kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Experience the ultimate coastal getaway at Ocean Point in Tavernier, Florida. Nestled along the stunning shores of the A ...
From $199 per night (USD)VRBO
From $412 per night (USD)VRBO
Seeking Paradise in the Keys? Dock for 35’ boat and pool & beach access included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This waterfront home has a cozy coastal feel with a master bathroom that has a king bed and a full bath. The second bed ...
From $412 per night (USD)VRBO
From $255 per night (USD)VRBO
**THE OSPREY'S NEST @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Want to be in ...
From $255 per night (USD)VRBO
From $300 per night (USD)Expedia
3BR Oasis, Key Largo - Central Paradise Location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Cozy and Great Remodeled 3/3 House in the heart of Key Largo! Enjoy this beautiful destination near world class fishing, ...
From $300 per night (USD)Expedia
From $250 per night (USD)VRBO
Lower Keys Home getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 30
This lovely 2 bedroom is close to many popular restaurants and is only 35 min from key west. Very close to several boat ...
From $250 per night (USD)VRBO
From $275 per night (USD)Expedia
P76 - 33 Kyle Way in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seaside SerenityThis spacious 2 bedroom, 2 bathroom, open waterfront home is located at the south end of Marathon. With ...
From $275 per night (USD)Expedia
From $350 per night (USD)VRBO
Islamorada Home on Canal with Private Beach Access\n\/ 4 bedroom 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
This luxurious 4 bedroom, 3 bathroom house offers exceptional opportunity to experience the Florida keys in style with i ...
From $350 per night (USD)VRBO
From $280 per night (USD)Expedia
Cozy Corner 2A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This family friendly neighbor is peaceful and relaxing, very close to many restaurants and also 35 min from key west. Th ...
From $280 per night (USD)Expedia
From $239 per night (USD)VRBO
Sunny Key Largo Home w\/ Golf Cart & Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sunny skies, balmy breezes, and crisp cocktails await at this tropical 4-bed, 4-bath oasis in the Florida Keys. Make use ...
From $239 per night (USD)VRBO
From $991 per night (USD)Expedia
New! Windrose House by Brightwild | Pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: Welcome to Key Haven Estates! The Windrose is one of four newly designed homes on the exclusive island of Key H ...
From $991 per night (USD)Expedia
From $91 per night (USD)VRBO
RV by the Sea - Glamping in the Keys - Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Create unique experiences and memories at this rare property nestled in the heart of Key Largo in a peaceful, quiet 40 a ...
From $91 per night (USD)VRBO
From $216 per night (USD)Expedia
Steps to the Ocean & Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to paradise in a new 1 bed/2 bath centrally located in Marathon. Our condo is steps away from open ocean views, w ...
From $216 per night (USD)Expedia
From $223 per night (USD)VRBO
Gated Oceanfront Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy your tropical getaway at this condo, within the gated, newly built, Ocean Isles Fishing Village, centrally located ...
From $223 per night (USD)VRBO
From $220 per night (USD)Expedia
Oceanfront Getaway in Marathon!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy your tropical getaway at this condo, within the gated, newly built, Ocean Isles Fishing Village, centrally located ...
From $220 per night (USD)Expedia
From $225 per night (USD)VRBO
Keys paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Mar is an beautiful 3 bedroom home nestled among tropical foliage. There are three bedrooms and two baths on the h ...
From $225 per night (USD)VRBO
From $423 per night (USD)Expedia
Vista Del Mar ~ Private Pool Home with Open Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Vista Del Mar, our luxurious vacation rental property nestled in the breathtaking Florida Keys. Prepare to be ...
From $423 per night (USD)Expedia
From $410 per night (USD)VRBO
Sunset Serenade - Sunset Key
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
The first time you arrive to Key West everything indicates that you’ve reached the last tropical island along the ribbon ...
From $410 per night (USD)VRBO
From $348 per night (USD)VRBO
Coastal house in the Florida Keys with pool in a private area.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Fresh Coastal House at the Florida Keys. Enjoy a slice of paradise at Key Largo, Florida. Located in a quiet dead-end s ...
From $348 per night (USD)VRBO
From $500 per night (USD)VRBO
BE AS YOU ARE - 3 Bedroom \/ 3 Bathroom - Mid Town KEY WEST w\/ POOL
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegantly renovated and furnished with guest comfort and enjoyment in mind we would like to welcome you to “Be as you ar ...
From $500 per night (USD)VRBO
From $200 per night (USD)VRBO
Discover Your Bliss. Your Tropical Waterfront Paradise Awaits!\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Embrace the waterfront lifestyle with a spacious and well-maintained 2-bed/2-bath canal front home with direct ocean acc ...
From $200 per night (USD)VRBO
From $135 per night (USD)VRBO
Sunny FL keys home on a canal! Boaters paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Updated and fully furnished 2 bedroom 2 bath home on a canal with direct ocean access. 40 ft dock available for boaters ...
From $135 per night (USD)VRBO
From $196 per night (USD)Expedia
Waterfront charmer with plunge pool, covered patio, and bikes - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Bonito Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $196 per night (USD)Expedia
Click For PricingVRBO
Coconut Mallory Resort in Key West - 2 Bedroom Condo\/Marina\/Gumbos Bar & Grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Resort and Marina in Key West 2 Bedroom 2 Bath Condo partial fantasy fest 10/28/23 - 11/4-23 (Saturday t ...
Click For PricingVRBO
From $156 per night (USD)VRBO
Fully updated Keys home with pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
A true Key's paradise awaits you at this fully updated 4 bedroom/4 bathroom home, just one block from the exclusive priv ...
From $156 per night (USD)VRBO
From $138 per night (USD)VRBO
Exec Bay townhouse w\/heated pool, marina, beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and experience the beauty and tranquility of the Florida Keys at Executive Bay Club! Enjoy gorgeous views from this ...
From $138 per night (USD)VRBO
From $552 per night (USD)Expedia
Grand waterfront estate with 220’ dock, heated pool, & outdoor kitchen
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Casa Del Lago Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $552 per night (USD)Expedia
From $350 per night (USD)VRBO
Canal-front home with private dock, hot tub, water views, kayaks, & deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two J’s Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $350 per night (USD)VRBO
From $180 per night (USD)VRBO
Bayfront Paradise! Home right on the bay with EPIC unobstructed sunset views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our paradise! Our cozy home is right on the bay with gorgeous sunsets right from the dock. The home comes wit ...
From $180 per night (USD)VRBO
From $777 per night (USD)VRBO
Islamorada Keys Waterfront .Pool Luxury Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront Islamorada 4 bedroom 3 bathroom home on the absolute best Waterfront Deep Water Canal w direct ocean access. ...
From $777 per night (USD)VRBO
From $167 per night (USD)Expedia
Poolside tropical paradise in Key West! The Salty Conch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The Salty Conch is tucked away in the gated community of The Key West Golf Club with 24/7 security for your peace of min ...
From $167 per night (USD)Expedia
From $287 per night (USD)VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony 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 $3750 per night (USD)VRBO
Barefoot Key - Key Largo, Florida
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 14
Looking to rent a private, boutique hotel for your family and friends? Look no further… Welcome to the Barefoot Key and ...
From $3750 per night (USD)VRBO
From $934 per night (USD)VRBO
The Villa by the Bay Unit #2
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy a beautiful experience in the heart of Islamorada, the fishing capital of the world! Coral Cove is a gated small c ...
From $934 per night (USD)VRBO
From $183 per night (USD)VRBO
Kampground Paradise w\/ Kayaks, Heated Pool, Marina!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy the ocean just steps away from Life in Paradise! This hidden gem is located in the community of Key Largo Kampgrou ...
From $183 per night (USD)VRBO
From $295 per night (USD)VRBO
Beautiful vacation home by the ocean to have fun with family and friends.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful Waterfront property with direct access to the Atlantic Ocean will offer you a memorable and beautiful vac ...
From $295 per night (USD)VRBO
From $375 per night (USD)Expedia
Our Piece of Paradise-
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $375 per night (USD)Expedia
From $307 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 $307 per night (USD)VRBO
From $272 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 $272 per night (USD)Expedia
From $141 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 $141 per night (USD)VRBO
From $140 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 $140 per night (USD)Expedia
From $299 per night (USD)VRBO
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)VRBO
From $289 per night (USD)Expedia
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)Expedia
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 PricingExpedia
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 PricingExpedia
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
Click For PricingVRBO
Hyatt Residence Club, Beach House, Two Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A tropical getaway in classic Key West style Escape to a Florida destination renowned for its hospitality and relaxed ...
Click For PricingVRBO
From $163 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 $163 per night (USD)VRBO
From $367 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 $367 per night (USD)Expedia
From $441 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 $441 per night (USD)VRBO
From $361 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 $361 per night (USD)Expedia
From $300 per night (USD)VRBO
Seaside charm w\/heated pool and ocean view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into a world of understated elegance in the Coco Plum area of Marathon, FL. Our newly renovated 1BR condo is an inv ...
From $300 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 $417 per night (USD)VRBO
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 $417 per night (USD)VRBO
From $136 per night (USD)Expedia
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 $136 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
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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 $358 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 $358 per night (USD)VRBO
From $300 per night (USD)Expedia
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 $300 per night (USD)Expedia
From $215 per night (USD)VRBO
Dolphin Cove~ Stunning Waterfront Townhome w Pool- 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 $215 per night (USD)VRBO
From $312 per night (USD)Expedia
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 $312 per night (USD)Expedia
From $154 per night (USD)VRBO
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 $154 per night (USD)VRBO
From $450 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 $450 per night (USD)VRBO
From $129 per night (USD)VRBO
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 $129 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 $413 per night (USD)VRBO
Key West Lighthouse Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unexpected Location. The Key West Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suites Coll ...
From $413 per night (USD)VRBO
From $371 per night (USD)Expedia
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 $371 per night (USD)Expedia
From $300 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 $300 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 $240 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 $240 per night (USD)VRBO
From $255 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 $255 per night (USD)Expedia
From $765 per night (USD)VRBO
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)VRBO
From $283 per night (USD)VRBO
L` Attitude Adjustment | 3 Bed, 2 Bath
- 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 $283 per night (USD)VRBO
Click For PricingVRBO
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 ...
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From $1123 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 $1123 per night (USD)VRBO