Florida Keys Rentals
- From $350 per night (USD)
VRBO
P31 - 11785 5th Ave. Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
New on the rental market! - Location! Location! Location! This 2 bedroom, 2 bath home is beautiful and boasts stunning o ...
From $350 per night (USD)VRBO
- From $858 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 $858 per night (USD)Expedia
- From $429 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 $429 per night (USD)VRBO
- From $1287 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 $1287 per night (USD)Expedia
- From $429 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 $429 per night (USD)VRBO
- From $1021 per night (USD)
VRBO
Dive Into Your Dream Vacation! Pool, Pet-friendly, Beachfront Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1021 per night (USD)VRBO
- From $1595 per night (USD)
VRBO
Sunny Vacay! 2 Garden View Units w\/ Kitchenette, Outdoor Pool, Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1595 per night (USD)VRBO
- From $797 per night (USD)
VRBO
Beach Adventure! Unit w\/ Kitchenette, Outdoor Pool, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $797 per night (USD)VRBO
- From $1838 per night (USD)
VRBO
Enjoyable Stay! Beachfront Location, With Full Kitchen, Free Parking, Pool!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1838 per night (USD)VRBO
- From $1496 per night (USD)
VRBO
Spacious 3BR Unit w\/ Kitchen Perfect for Groups! w\/ Outdoor Pool, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1496 per night (USD)VRBO
- From $373 per night (USD)
VRBO
Excellent Choice! Pet-friendly Property, Pool, Free Parking Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $373 per night (USD)VRBO
- From $368 per night (USD)
VRBO
Hassle-free Stay! Garden View, w\/ Kitchenette, Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $368 per night (USD)VRBO
- From $1165 per night (USD)
VRBO
Best Summer Choice! Unit with Full Kitchen, Beachfront, Outdoor Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1165 per night (USD)VRBO
- From $549 per night (USD)
VRBO
Enjoy Relaxing Views! Ocean Front, Pets Allowed, Free Parking Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $549 per night (USD)VRBO
- From $1406 per night (USD)
VRBO
Excellent Choice for Families! Full Kitchen, Pool, Pet-friendly, Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1406 per night (USD)VRBO
- From $937 per night (USD)
VRBO
Stunning Ocean View! Beachfront Property, w\/ Pool, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $937 per night (USD)VRBO
- From $1651 per night (USD)
VRBO
Shell House Luxury Villa in Key Largo with Resort Privileges
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
4 Bed 4.5 Bath | 3888 SF | 3-Story Home | Multi Terrace | Oceanfront Pool | Clubhouse | Covered Parking | Playa Largo Re ...
From $1651 per night (USD)VRBO
- From $1616 per night (USD)
Expedia
Coastal Oasis Luxury Villa in Key Largo with Resort Privileges
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bed 4.5 Bath | 3388 SF | 3-Story Home | Multi Terrace | Oceanfront Pool | Clubhouse | Covered Parking | Playa Largo Re ...
From $1616 per night (USD)Expedia
- From $1538 per night (USD)
VRBO
Sea-Esta Luxury Villa in Key Largo with Resort Privileges
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
3 Bed 2.5 Bath | 3318 SF | 3-Story Home | Multi Terrace | Oceanfront Pool | Clubhouse | Covered Parking | Playa Largo Re ...
From $1538 per night (USD)VRBO
- From $1411 per night (USD)
Expedia
Twilight Luxury Villa in Key Largo with Resort Privileges
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bed 4.5 Bath | 3888 SF | 3-Story Home | Multi Terrace | Oceanfront Pool | Clubhouse | Covered Parking | Playa Largo Re ...
From $1411 per night (USD)Expedia
- From $1573 per night (USD)
VRBO
Latitudes Luxury Villa in Key Largo with Resort Privileges
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bed 4.5 Bath | 3888 SF | 3-Story Home | Multi Terrace | Oceanfront Pool | Clubhouse | Covered Parking | Playa Largo Re ...
From $1573 per night (USD)VRBO
- From $1721 per night (USD)
Expedia
The Lookout Luxury Villa in Key Largo with Resort Privileges
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bed 4.5 Bath | 3888 SF | 3-Story Home | Multi Terrace | Oceanfront Pool | Clubhouse | Covered Parking | Playa Largo Re ...
From $1721 per night (USD)Expedia
- From $1443 per night (USD)
VRBO
Sea Haven Luxury Villa in Key Largo with Resort Privileges
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bed 4.5 Bath | 3888 SF | 3-Story Home | Multi Terrace | Oceanfront Pool | Clubhouse | Covered Parking | Playa Largo Re ...
From $1443 per night (USD)VRBO
- From $1562 per night (USD)
Expedia
Sandcastle Luxury Villa in Key Largo with Resort Privileges
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
4 Bed 4.5 Bath | 3888 SF | 3-Story Home | Multi Terrace | Oceanfront Pool | Clubhouse | Covered Parking | Playa Largo Re ...
From $1562 per night (USD)Expedia
- From $534 per night (USD)
VRBO
Happy Tingler With Pool Tiki and 100 ft of Dockage Right Next to Sombrero Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Dreaming of the beach? Look no further...located in the small subdivision just a couple of blocks from Sombrero beach, ...
From $534 per night (USD)VRBO
- From $885 per night (USD)
VRBO
Tropical Shores | Sublime resort-style retreat with 3 bed\/3.5 baths
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to paradise at this secluded resort-style retreat nestled on serene Big Pine Key. Spanning over 3 acres, this ope ...
From $885 per night (USD)VRBO
- From $391 per night (USD)
VRBO
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! MODERN MAJEST ...
From $391 per night (USD)VRBO
- From $413 per night (USD)
Expedia
P08 - Beautiful 4 bedroom, 3 bathroom half Duplex in Key Colony with private...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely two story half duplex in Key Colony Beach offers 4 bedrooms, 3 bathrooms and abundant living space on both l ...
From $413 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Brand New '23 Canal Home - 3BR\/3BA, Sleeps 8, with Pool, 50' Dock, & Cabana Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our brand new (SEPTEMBER 2023), thoughtfully curated Key Colony Beach canal front home! Each side of the dupl ...
From $300 per night (USD)VRBO
- From $270 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 $270 per night (USD)Expedia
- From $510 per night (USD)
VRBO
Impressive 4\/4 waterfront family\/pet friendly home in beautiful Duck Key FL.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy this Cape Cod-style beautiful and cozy two-story waterfront home with two separate living areas and two separate s ...
From $510 per night (USD)VRBO
- From $200 per night (USD)
VRBO
The Elizabeth #1 Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are pleased to introduce The Fleming Suite at The Bayview House , a 1-bedroom, 1-bathroom nightly rental. Located in ...
From $200 per night (USD)VRBO
- From $275 per night (USD)
VRBO
The Fleming #3 Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are pleased to introduce The Fleming Suite at The Bayview House , a 1-bedroom, 1-bathroom nightly rental. Located in ...
From $275 per night (USD)VRBO
- From $235 per night (USD)
Expedia
New Listing-Golf Course Charmer!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully ...
From $235 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Beautiful spacious completely remodeled townhouse in Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to paradise in this beautiful 3 bedroom 3 bathroom Corner unit townhouse. The master bedroom has a king bed with ...
From $250 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Tropical Paradise in Marathon Key-minutes from Sombrero beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful condo located in the heart of Marathon Key! 5 minutes to Sombrero beach which has a playground, bbq grills, an ...
From $200 per night (USD)VRBO
- From $300 per night (USD)
VRBO
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)VRBO
- From $315 per night (USD)
Expedia
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 $315 per night (USD)Expedia
- From $881 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 $881 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 $367 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 $367 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 $459 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 $459 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 $2036 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 $2036 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 $300 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 $300 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 $155 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 $155 per night (USD)Expedia
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $285 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 $285 per night (USD)VRBO
- Click For Pricing
VRBO
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 $195 per night (USD)
Expedia
Islamorada Townhome w\/ Pool & Beach Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Discover your own tropical paradise at this lovely 2-bedroom, 2-bath vacation rental in Islamorada, FL! Located just ste ...
From $195 per night (USD)Expedia
- From $821 per night (USD)
VRBO
Sandy Beach Cove🏝️🏖️ Private Beach compound with dock and boat space to 28’feet
- 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)VRBO
- From $367 per night (USD)
Expedia
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)Expedia
- From $164 per night (USD)
VRBO
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 $164 per night (USD)VRBO
- From $299 per night (USD)
Expedia
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 $299 per night (USD)Expedia
- From $305 per night (USD)
VRBO
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 $305 per night (USD)VRBO
- From $690 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 $690 per night (USD)Expedia
- From $225 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 $225 per night (USD)VRBO
- From $350 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 $350 per night (USD)VRBO
- From $222 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 $222 per night (USD)VRBO
- From $637 per night (USD)
Expedia
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 $637 per night (USD)Expedia
- From $242 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 $242 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 $368 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 $368 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 $955 per night (USD)
VRBO
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 $955 per night (USD)VRBO
- From $103 per night (USD)
Expedia
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 $103 per night (USD)Expedia
- From $211 per night (USD)
VRBO
Steps to the Ocean & Heated Pool
- Bedrooms:
- 2
- 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 $211 per night (USD)VRBO
- From $223 per night (USD)
Expedia
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)Expedia
- From $199 per night (USD)
VRBO
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 $199 per night (USD)VRBO
- 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 $530 per night (USD)
VRBO
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 $530 per night (USD)VRBO
- 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 $339 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 $339 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 $153 per night (USD)
VRBO
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 $153 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $155 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 $155 per night (USD)VRBO
- From $163 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 $163 per night (USD)VRBO
- From $552 per night (USD)
VRBO
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)VRBO
- From $350 per night (USD)
Expedia
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)Expedia
- 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 $773 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 $773 per night (USD)VRBO
- From $166 per night (USD)
VRBO
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 $166 per night (USD)VRBO
- From $294 per night (USD)
Expedia
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 $294 per night (USD)Expedia
- 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)
Expedia
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)Expedia
- 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)
VRBO
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)VRBO
- From $250 per night (USD)
Expedia
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)Expedia