Florida Keys Rentals
- From $2033 per night (USD)
VRBO
Private Beach Bayside 6 Bedroom Resort Home with Pool, Dock, & Garage
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 12
Owner managed property. We would love to welcome you to our oceanfront retreat, please note we take great care of our pr ...
From $2033 per night (USD)VRBO
- From $405 per night (USD)
Expedia
4-bedroom airport community house in Tavernier
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
*MORE PHOTOS TO COME AFTER RENOVATIONS* Experience Tavernier like a local in this 4-bedroom house. Step into a wonderful ...
From $405 per night (USD)Expedia
- From $279 per night (USD)
VRBO
Charming 3-bedroom house in Islamorada with Marina access.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This Islamorada house boasts 3 inviting bedrooms. Bedrooms are furnished with 1 king bed and 2 full beds, ensuring a com ...
From $279 per night (USD)VRBO
- From $1481 per night (USD)
Expedia
New Large Luxury Rental - Sombrero Palms
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Sombrero Palms, a captivating retreat just a stone's throw away from the shores of Sombrero Beach. This charming rental ...
From $1481 per night (USD)Expedia
- From $316 per night (USD)
VRBO
Welcome to Kokomo Cottage-A311
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautifully renovated 3 bedroom, 2 bathroom beach getaway is waiting for your perfect escape. See the Sunset and s ...
From $316 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Sandy Toes Retreat-A310
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautifully renovated 3 bedroom, 2 bathroom beach getaway is waiting for your perfect escape. See the Sunset and s ...
From $315 per night (USD)Expedia
- From $320 per night (USD)
VRBO
Florida Keys Condo with Pool, Beach Access, Marina, Pickleball & More
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Tarpon Cove at Ocean Pointe Resort! Experience a high-quality resort that combines the comforts of a first-cl ...
From $320 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Take it Keysie, Waterfront House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to “Take it Keysie” your tropical/waterfront retreat in Marathon, Florida! Located in the heart of the Florida ...
From $399 per night (USD)Expedia
- From $322 per night (USD)
VRBO
Sunkissed Bungalow-B205
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A perfect beach getaway in Key West! See the Sunset and stroll the sidewalks at this fabulous location away from the cr ...
From $322 per night (USD)VRBO
- From $780 per night (USD)
VRBO
The Coral House in Key Colony 3 Bed, 2 Bath Home Deep water dock & Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The legendary Coral House available to rent for the first time ever! One of the most beautiful lots and sunset views in ...
From $780 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Green Turtle Cottage KW 1 Block from Mile Marker 0 in Gated Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom 2.5 bath private home in a secluded section of the gated community of Truman Annex quietly sits among pre ...
From $600 per night (USD)VRBO
- From $442 per night (USD)
VRBO
Charming 3-bedroom house with Amazing Gulf Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Have a truly blissful vacation at this charming, Gulf Front home that sits on one acre of pristine property on exclusive ...
From $442 per night (USD)VRBO
- From $712 per night (USD)
VRBO
Cozy 3-bedroom house with WiFi, AC in gorgeous Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 2
This 3-bedroom house is perfect for your escape to Key Largo. With its brilliant location, you'll be just moments away f ...
From $712 per night (USD)VRBO
- From $244 per night (USD)
Expedia
Island Comfort at Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your Keys Getaway! Escape to paradise with this charming 3-bd, 2-ba canal-front home, perfect for those looking to unwin ...
From $244 per night (USD)Expedia
- From $684 per night (USD)
VRBO
NEW CONSTRUCTION-4-Bedroom- 3.5 Bathroom - Cudjoe Key- Canal Front W\/ Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Unwind at the Artist House on Tarpon Lane on Cudjoe Key! This perfect new construction waterfront home checks all the ...
From $684 per night (USD)VRBO
- From $247 per night (USD)
Expedia
Tropical cottage with private pool, two blocks from Duval - near Hemingway House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
The Conch-Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $247 per night (USD)Expedia
- From $735 per night (USD)
VRBO
Beachside Bliss ~ Private Beach and Pool Home!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Beachside Bliss Step into your coastal sanctuary! Immerse yourself in the Southeast Exposure, letting the sun's rays em ...
From $735 per night (USD)VRBO
- From $393 per night (USD)
Expedia
When Paradise is Key: Tropical Oceanfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
☀️ Discover the ultimate beachfront getaway in our newly renovated two-bedroom, two-bathroom condo, perfectly designed t ...
From $393 per night (USD)Expedia
- From $379 per night (USD)
VRBO
Casa Margarita Islamorada, Paradise awaits!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Islamorada like a local in this 3-bedroom 3-bath pool home. This beautiful recently remodeled 3 bed 3 bath po ...
From $379 per night (USD)VRBO
- From $334 per night (USD)
Expedia
Family 2BR w\/ Ocean Views, Pool & Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $334 per night (USD)Expedia
- From $359 per night (USD)
VRBO
2BR Condo w\/ Partial Ocean Views, Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $359 per night (USD)VRBO
- From $329 per night (USD)
Expedia
2BR Condo w\/ Ocean Views, Pool & Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $329 per night (USD)Expedia
- From $232 per night (USD)
VRBO
1BR w\/ Partial Ocean View, Pool & Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $232 per night (USD)VRBO
- From $354 per night (USD)
Expedia
Key Largo 2BR - Ocean View, Pool & Near Bird Sanctuary
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)Expedia
- From $359 per night (USD)
VRBO
Key Largo 2BR w\/ Partial Ocean Views & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $359 per night (USD)VRBO
- From $371 per night (USD)
Expedia
Escape to the Keys, Ocean View 2BR - Pool, Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $371 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Ocean View 2 Bedroom Condo – Pool, Beach, & More
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)VRBO
- From $353 per night (USD)
Expedia
2BR Condo w\/ Ocean View, Pool & Tropical Setting
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $353 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Key Largo 2 BR Condo - Ocean Views, Pool, Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)VRBO
- From $359 per night (USD)
Expedia
Family-Friendly 2BR w\/ Views, Pool, & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $359 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Couples 2BR w\/ Ocean View, Pool & Tropical Setting
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)VRBO
- From $354 per night (USD)
Expedia
Family 2BR w\/ Ocean View, Pool & Tropical Landscaping
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Key Largo Getaway 2BR - Ocean View, Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)VRBO
- From $353 per night (USD)
Expedia
Ocean View 2BR - Pool, Beach – Relax. Unwind.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $353 per night (USD)Expedia
- From $339 per night (USD)
VRBO
2BR w\/ Ocean Views, Pool, Beach, Near Pennekamp Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $339 per night (USD)VRBO
- From $362 per night (USD)
Expedia
Couples' Getaway 2BR w\/ Ocean View, Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $362 per night (USD)Expedia
- From $354 per night (USD)
VRBO
2BR Ocean View Condo, Pool, Near Marine Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)VRBO
- From $354 per night (USD)
Expedia
2BR Condo w\/ Ocean Views, Tropical Landscaping, Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Couples' Retreat 2BR w\/ Ocean Views, Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)VRBO
- From $353 per night (USD)
Expedia
Ocean View 2BR - Pool & Near Bird Sanctuary
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $353 per night (USD)Expedia
- From $241 per night (USD)
VRBO
Family 2BR w\/ Ocean View, Pool & Near Marine Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $241 per night (USD)VRBO
- From $354 per night (USD)
Expedia
2BR Condo w\/ Ocean Views, Private Beach & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)Expedia
- From $351 per night (USD)
VRBO
Ocean View 2BR - Pool, Beach & Sanctuary
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $351 per night (USD)VRBO
- From $381 per night (USD)
Expedia
2BR w\/ Ocean View, Pool, Beach, Near Coral Reef Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $381 per night (USD)Expedia
- From $367 per night (USD)
VRBO
Family-Friendly 2BR w\/ Ocean View, Pool, Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $367 per night (USD)VRBO
- From $340 per night (USD)
Expedia
Family-Friendly 2BR w\/ Ocean Views, Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $340 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Ocean View 2BR - Pool, Beach & Tropical Landscaping
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)VRBO
- From $332 per night (USD)
Expedia
Cozy 2BR Condo w\/ Ocean Views, Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $332 per night (USD)Expedia
- From $371 per night (USD)
VRBO
Relaxing 2BR w\/ Ocean View, Pool & Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $371 per night (USD)VRBO
- From $354 per night (USD)
Expedia
2BR - Ocean View, Pool & Near Founders Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Friends' Getaway 2BR w\/ Ocean View, Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $365 per night (USD)VRBO
- From $354 per night (USD)
Expedia
Key Largo 2BR Condo - Ocean View, Pool, and Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)Expedia
- From $1072 per night (USD)
VRBO
Secluded and Private Monthly Tropical Modern Oasis with a Large Pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Experience Key West like a local in this 4-bedroom house with a large saltwater pool. Step into your own private tropic ...
From $1072 per night (USD)VRBO
- From $694 per night (USD)
Expedia
4-bedroom house in Islamorada, The Sportfishing Capital of the World
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA cana ...
From $694 per night (USD)Expedia
- From $390 per night (USD)
VRBO
Boomerang Boathouse in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NEW UNIT! MARCH Still Open!“Richley individual” yet “classic Key West” are phrases that echo from Boomerang Boathouse, a ...
From $390 per night (USD)VRBO
- From $985 per night (USD)
VRBO
Double Queen with Balcony, Ocean View, Isla Bella, Beach & Pool, Spa Wellness
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $985 per night (USD)VRBO
- From $1301 per night (USD)
VRBO
Oceanfront Veranda King Suite, Beach Access, Isla Bella, Right Off Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $1301 per night (USD)VRBO
- From $1170 per night (USD)
VRBO
Right in the Middle of Florida Keys | Relaxing Private Beach & Outdoor Pools
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $1170 per night (USD)VRBO
- From $557 per night (USD)
VRBO
Oceanfront Accommodation | Enjoy Breakfast with a Scenic View on Your Veranda
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $557 per night (USD)VRBO
- From $1231 per night (USD)
VRBO
2 Units | Double Queen Oceanfront w\/ Balcony, Scenic Cycling, Isla Bella
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $1231 per night (USD)VRBO
- From $491 per night (USD)
VRBO
Scenic Veranda Double Queen, Isla Bella, Private Beach, Near Seven Miles Bridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $491 per night (USD)VRBO
- From $1231 per night (USD)
VRBO
2 Oceant Front Room w\/ Own Balcony | Short Drive to Seven Mile Bridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $1231 per night (USD)VRBO
- From $1064 per night (USD)
VRBO
Relaxing Beachside Resort w\/ 5 Outdoor Pools | Near Famous Seven Mile Bridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $1064 per night (USD)VRBO
- From $1231 per night (USD)
VRBO
Gorgeous Beach Front Resort | Short Drive from Iconic Seven Mile Bridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $1231 per night (USD)VRBO
- From $1314 per night (USD)
VRBO
King Balcony Suite, Beachfront Experience, Isla Bella Beach, Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your ultimate oceanfront escape, perfectly located in the heart of the Florida Keys. Here, you are in the pri ...
From $1314 per night (USD)VRBO
- From $473 per night (USD)
Expedia
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Florida Keys are located off the southern coast of Florida. They are a string of tropical islands stretching about 1 ...
From $473 per night (USD)Expedia
- From $431 per night (USD)
VRBO
Cozy 1BR, Spacious Felix Boat Experience in Key West, Perry Marina - Wifi & AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome aboard our newly renovated houseboat nestled in the Perry Marina! Uniquely crafted by legendary artist, immerse ...
From $431 per night (USD)VRBO
- From $551 per night (USD)
Expedia
Atlantis House's Banyan Suite-voted top 25 in USA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Banyan Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situat ...
From $551 per night (USD)Expedia
- From $727 per night (USD)
VRBO
Atlantis House's Palm Suite-voted top 25 in USA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Palm Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situated ...
From $727 per night (USD)VRBO
- From $459 per night (USD)
VRBO
Key West King Escape, Fairfield Inn, Outdoor Swimming Pool | Near Mallory Square
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $459 per night (USD)VRBO
- From $509 per night (USD)
VRBO
Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $509 per night (USD)VRBO
- From $2691 per night (USD)
VRBO
Keys Mansion + Guitar Pool + Hot Tub!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Hosted by a Hilton Hotel General Manager, 5 star customer service is a guarantee! Escape to paradise in this stunning Fl ...
From $2691 per night (USD)VRBO
- From $485 per night (USD)
VRBO
The Perfect Catch: Family Fun and Boater's Bliss in the Keys!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
THE PERFECT CATCH! Escape to paradise in our private stunning Summerland Key Home! This beautifully remodeled residence ...
From $485 per night (USD)VRBO
- From $354 per night (USD)
Expedia
Hideaway in Key Largo 2BR Condo - Ocean View, Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $354 per night (USD)Expedia
- From $380 per night (USD)
VRBO
Ocean View 2BR Condo – Pool, Beach, near the fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $380 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Couples' 2BR w\/ Ocean View, Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $315 per night (USD)Expedia
- From $358 per night (USD)
VRBO
Family 2BR w\/ Ocean View, Pool & Tropical Setting
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $358 per night (USD)VRBO
- From $522 per night (USD)
VRBO
Newly Renovated Hotel w\/ Outdoor Pool | Short Drive to Historic Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $522 per night (USD)VRBO
- From $522 per night (USD)
VRBO
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $522 per night (USD)VRBO
- From $492 per night (USD)
Expedia
**SWORDFISH SANCTUARY @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! In the same w ...
From $492 per night (USD)Expedia
- From $205 per night (USD)
VRBO
Serene & expansive waterfront property located in Key Largo Florida.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Come relax & enjoy everything the Florida Keys has to offer. Casa Bayview is conveniently located in Key Largo Florida. ...
From $205 per night (USD)VRBO
- From $2344 per night (USD)
Expedia
OCEAN FRONT OASIS PRIVATE RESORT- MOST EXCLUSIVE SECLUDED PENINSULA
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 8
First time offered - only property of its kind in the keys, as featured in Global Mansions - Wall Street Journal. A tru ...
From $2344 per night (USD)Expedia
- From $1226 per night (USD)
VRBO
Luxurious Gated Key West Oasis: 3 Bed + 4th Floor Sleeper, Elevator, & Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Immerse yourself in the heart of Old Town Key West and discover a luxurious retreat where island living meets modern com ...
From $1226 per night (USD)VRBO
- From $327 per night (USD)
Expedia
Key Largo 2BR - Partial Ocean Views, Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $327 per night (USD)Expedia
- From $612 per night (USD)
VRBO
New! The Green Pineapple - Balcony on Duval!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Beautiful 4-bedroom, 3-bath monthly rental located on Key West's famous Duval Street. Guests enjoy easy access ...
From $612 per night (USD)VRBO
- From $596 per night (USD)
Expedia
New! Coastal Rose - Bright Loft with High Ceilings!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $596 per night (USD)Expedia
- From $440 per night (USD)
VRBO
New! Rose Petal Petite Suite - Pool & Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Located in downtown Key West, the 'Rose Petal Petite Suite' offers a cozy and charming accommodation experience ...
From $440 per night (USD)VRBO
- From $956 per night (USD)
Expedia
New! Rose Key Cottage- Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $956 per night (USD)Expedia
- From $735 per night (USD)
VRBO
Dog-friendly Keys house with pool, screened-in patio & children's items
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Cheeseburger Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $735 per night (USD)VRBO
- From $184 per night (USD)
Expedia
Waterfront Key Largo Oasis w\/ Boat Dock & Swim Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Find your paradise at 'Villa Bella,' a 2-bedroom, 1.5-bath vacation rental in Key Largo! With its canal view, ocean acce ...
From $184 per night (USD)Expedia
- From $966 per night (USD)
VRBO
Emerald Oasis ~ Lux Waterfront Gem ~ Heated Pool ~ Kayaks
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Indulge in this luxurious 4BR 4.5BA house nestled on a gorgeous waterfront property in Marathon, FL. This spaci ...
From $966 per night (USD)VRBO
- From $906 per night (USD)
Expedia
**INFINITE HORIZONS @ BIG COPPITT** Waterfront Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! As if a vacat ...
From $906 per night (USD)Expedia
- From $715 per night (USD)
VRBO
3 Bedroom Ocean Front Villa next to the John Pennekamp Coral Reef State Park
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This is a 2 story Ocean Front Villa. There are 2 bedrooms, 2 bathrooms, living room, dining room, Kitchen and balcony on ...
From $715 per night (USD)VRBO
- From $310 per night (USD)
Expedia
New Property! An Island Siesta
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...
From $310 per night (USD)Expedia
- Click For Pricing
VRBO
Southernmost Beach Resort provides flawless service and all the necessary facilities for ...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Southernmost Beach Resort provides flawless service and all the necessary facilities for visitors. Stay connected with y ...
Click For PricingVRBO
- From $150 per night (USD)
VRBO
Charming canal front 2-bedroom mobile home with WiFi and AC in Little Torch Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRBO required we create a new listing after 9 years and 20 perfect 5 star ratings!!! We had the same guests for the pas ...
From $150 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Cozy 2-bedroom mobile home in enchanting Marathon with WiFi, AC.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Grassy Key Paradise VACA-24-72 Are you looking for a place in paradise? Paradise Place is located in Marathon, FL surr ...
From $399 per night (USD)Expedia
- From $1303 per night (USD)
VRBO
The Oasis in Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover beauty, tranquility, and elegance in one extraordinary package. Book now to create everlasting memories! Experi ...
From $1303 per night (USD)VRBO
- From $574 per night (USD)
VRBO
Luxury oasis with resort-style pool in heart of Key Largo!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this luxurious waterfront retreat, newly renovated to offer unparalleled comfort and style. This tastefully d ...
From $574 per night (USD)VRBO
- From $339 per night (USD)
Expedia
P61 - 2 Bed, 2 Bath with coastal chic vibe and private pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom, 2 bath home boasts a chic coastal vibe. The outdoor living space of this home offers a private bac ...
From $339 per night (USD)Expedia