Florida Keys, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Florida Keys, Florida on RentalSaver.com!

Florida Keys Rentals

Filter

Popular Areas

Click For Pricing
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 ...
Click For Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $974 per night (USD)
VRBO
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 $974 per night (USD)
VRBO
From $916 per night (USD)
Expedia
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 $916 per night (USD)
Expedia
From $428 per night (USD)
VRBO
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 $428 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $779 per night (USD)
VRBO
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 $779 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Location Location! Beautiful views from every angle. Summerland Cove rare point
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 $479 per night (USD)
Expedia
From $599 per night (USD)
VRBO
Book Your Escape In Paradise at Stay Anchored at Sombrero
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 $599 per night (USD)
VRBO
From $570 per night (USD)
Expedia
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 $570 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Brand New Home, Resort Location, Pet Friendly, Oceanview
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This brand new home is sitting quietly behind a controlled access gate with a private balcony overlooking the Atlantic O ...
From $243 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $708 per night (USD)
VRBO
Conch Cottage: 4 BR, 3 BA House in Marathon, Sleeps 10
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 $708 per night (USD)
VRBO
From $363 per night (USD)
Expedia
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 $363 per night (USD)
Expedia
$Spectacular 4 bedroom 4 1\/2 bath villa on Tavernier Creek in Florida Keys.$
From $1162 per night (USD)
VRBO
Spectacular 4 bedroom 4 1\/2 bath villa on Tavernier Creek in Florida Keys.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Incomparable villa directly on Tavernier Creek with immediate access to ocean and bay. Fully fenced and gated. Manatees ...
From $1162 per night (USD)
VRBO
From $239 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 $239 per night (USD)
VRBO
From $208 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, access to gulf side dockage, a g ...
From $208 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Ocean Harbor Paradise in 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 $351 per night (USD)
Expedia
From $539 per night (USD)
VRBO
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 $539 per night (USD)
VRBO
From $594 per night (USD)
Expedia
NEW! Atlantic Oasis | Pool, Hot Tub & Near Beach!
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Summary: Atlantic Oasis is a true Key West "Conch Style" townhome consisting of over 1900 sq. ft. of beautiful living sp ...
From $594 per night (USD)
Expedia
From $209 per night (USD)
VRBO
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 $209 per night (USD)
VRBO
From $635 per night (USD)
Expedia
KCB ~ Aqua Vista ~ Luxury Waterfront Oasis with Pool and Dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
KCB ~ Aqua Vista Welcome to Aqua Vista, your ideal vacation retreat located in the heart of Key Colony Beach! This exqu ...
From $635 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Cayman Retreat | Cozy coastal pool home with boating on Ramrod Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your coastal retreat nestled within picturesque Breezeswept Beach Estates on Ramrod Key. Just three canals aw ...
From $368 per night (USD)
VRBO
From $546 per night (USD)
Expedia
**THE COZY STARFISH @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICES…
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE COZY STAR ...
From $546 per night (USD)
Expedia
From $920 per night (USD)
VRBO
Keys home overlooking the ocean and beautiful sunrises!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful oceanfront residence with pool, and modern renovations. Located in desirable Islamorada with access to a priva ...
From $920 per night (USD)
VRBO
From $264 per night (USD)
Expedia
A quiet Paradise sanctuary on a dead-end street overlooking Florida Bay.
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Greet the day with a sunrise over the bay. Situated on a peaceful, quiet dead-end street. Located within a 2 mile radius ...
From $264 per night (USD)
Expedia
$Paraiso Del Mar ~ Luxury Tropical Oasis w\/ Private Pool & 35` Dock!$
From $1194 per night (USD)
VRBO
Paraiso Del Mar ~ Luxury Tropical Oasis w\/ Private Pool & 35` Dock!
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
Paraíso Del Mar Introducing our newest luxury vacation rental nestled in the prestigious community of Marathon. This br ...
From $1194 per night (USD)
VRBO
From $425 per night (USD)
Expedia
NEW! Haven House | Waterfront Home, Amazing Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: The Haven House is truly heavenly on the quiet residential canals in Key Haven. This home boasts a modern water ...
From $425 per night (USD)
Expedia
From $729 per night (USD)
VRBO
Awai's Floating Villa - Luxury Houseboat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience Key West in a new way: aboard a luxury houseboat! From watching sunrise on the dock to watching suns ...
From $729 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Fisherman's Cove, Waterfront 3 Bed, 2 Bath home in Tavernier! Harry Harris Park!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Fisherman's Cove! This beautiful home is a new rental and ready to be your home away from home in the Florida ...
From $231 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Bayside Relaxing Home-BBQ-Pool+
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy RV in Key Largo offering a great location and the feel of home with 2 bedroom/1 bath, dinning area, with (3)TV, kit ...
From $248 per night (USD)
VRBO
From $760 per night (USD)
Expedia
Paradise Cove!30ft Dock Pool BBQ
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our stunning new property located in the heart of the Florida Keys in Key Colony Beach! This exquisite retreat offers ev ...
From $760 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Dolphin Den-Pool-Boat Ramp-BBQ
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Nestled in Key Largo, Florida, this cozy camper RV boasts a picturesque canal view and proximity to adventure! Just 5 mi ...
From $254 per night (USD)
VRBO
From $826 per night (USD)
Expedia
Villa Franchella ~ Gorgeous luxury home just minutes from the Gulf
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Villa Franchella NEW TO MARKET!! - Escape to paradise and experience the epitome of luxury living in this breathtaking ...
From $826 per night (USD)
Expedia
$Memories of a Lifetime! A one of a Kind Sailboat!\n$
From $462 per night (USD)
VRBO
Memories of a Lifetime! A one of a Kind Sailboat!\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Based in the incredible Perry Marina and Resort, your vacation aboard this stunning historical sailboat will be a treasu ...
From $462 per night (USD)
VRBO
$Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n$
From $1000 per night (USD)
Expedia
Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom ...
From $1000 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Little Venice Paradise~55` dock access to Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Little Venice Paradise Escape to paradise with this charming two-bedroom, two-bathroom canal-front vacation rental home ...
From $258 per night (USD)
VRBO
From $609 per night (USD)
Expedia
Bungalows at Sugarloaf Beach - Little Hammock
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Part of the Bungalows at Sugarloaf Beach Collection, Little Hammock features privacy and a unique outdoor rain shower th ...
From $609 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Beautifully Renovated Paradise with Pool and Tropical Gardens in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into paradise in this clean and impeccably appointed 2 bedroom, 2 bathroom house in Old Town. Located just 2 blocks ...
From $265 per night (USD)
VRBO
$Trendy 4\/4 just Steps to the Beach, Marina, 2 Pools, Coffee Bar, Instagram Wall$
From $827 per night (USD)
Expedia
Trendy 4\/4 just Steps to the Beach, Marina, 2 Pools, Coffee Bar, Instagram Wall
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
What we love about this property is it's different than anywhere else! A fun and modern 4-bedroom townhouse with an Inst ...
From $827 per night (USD)
Expedia
From $1794 per night (USD)
VRBO
Island Retreat: Daily Housekeeping, 3 Pools, Fitness Center Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1794 per night (USD)
VRBO
From $605 per night (USD)
VRBO
Island Paradise: Modern Unit, Latin Cuisine, Poolside Cocktails
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $605 per night (USD)
VRBO
From $2392 per night (USD)
VRBO
Key West Sanctuary: Daily Housekeeping, Tiki Bar, Fitness Center
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2392 per night (USD)
VRBO
$Sandpiper Cove: updated 2bed\/2bath beachfront condo with shared pool$
From $321 per night (USD)
Expedia
Sandpiper Cove: updated 2bed\/2bath beachfront condo with shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Sandpiper Cove - your exclusive beachfront sanctuary! This impeccably designed 2-bedroom, 2-bathroom condo i ...
From $321 per night (USD)
Expedia
From $3028 per night (USD)
VRBO
Island Oasis: New Property, Poolside Cocktails, Latin Cuisine On-Site
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $3028 per night (USD)
VRBO
From $4249 per night (USD)
VRBO
Key West Getaway: Private Balcony, 3 Pools, Fitness Center Access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $4249 per night (USD)
VRBO
From $2153 per night (USD)
VRBO
Duval Street Gem: Ocean-View Balcony, On-Site Dining, 3 Pools
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2153 per night (USD)
VRBO
From $1196 per night (USD)
VRBO
Key West Hideaway: Private Balcony, Tiki Bar, On-Site Restaurant
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1196 per night (USD)
VRBO
From $2285 per night (USD)
VRBO
Oceanfront Escape: Modern Design, 3 Pools, Bicycle Rentals
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2285 per night (USD)
VRBO
From $1614 per night (USD)
VRBO
Coastal Haven: Modern Unit, Poolside Cocktails, Latin Cuisine
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1614 per night (USD)
VRBO
From $544 per night (USD)
VRBO
Ocean Oasis: Daily Housekeeping, On-Site Dining, Fitness Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $544 per night (USD)
VRBO
From $832 per night (USD)
VRBO
Tropical Escape: Ocean-View Balcony, Tiki Bar, 3 Pools
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $832 per night (USD)
VRBO
$Oceanfront condo with large balcony, direct beach access, nautical theme, & W\/D$
From $405 per night (USD)
VRBO
Oceanfront condo with large balcony, direct beach access, nautical theme, & W\/D
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Turquoise Turtle #30 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $405 per night (USD)
VRBO
$Snowbird-friendly condo in oceanfront complex with heated pool, BBQ, W\/D, AC$
From $171 per night (USD)
Expedia
Snowbird-friendly condo in oceanfront complex with heated pool, BBQ, W\/D, AC
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Overseas Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $171 per night (USD)
Expedia
From $497 per night (USD)
VRBO
Duck Key Treat Get Away
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Want to enjoy some relaxing time here in the Florida Keys on the great Duck Key Island? Well look no more....this home ...
From $497 per night (USD)
VRBO
From $584 per night (USD)
Expedia
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Harbor Hideaway Villa 7066 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $584 per night (USD)
Expedia
$Waterfront Keys Paradise w\/ 10k LB Boat Lift$
From $195 per night (USD)
VRBO
Waterfront Keys Paradise w\/ 10k LB Boat Lift
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully remodeled 2/2 with washer/dryer included. A boater's dream situated directly on the water and seconds from t ...
From $195 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The Florida Keys are located off the southern coast of Florida. They are a string of tropical islands stretching about 1 ...
From $509 per night (USD)
Expedia
From $443 per night (USD)
VRBO
Waterfront Luxury Villa (35) with sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it's own tele ...
From $443 per night (USD)
VRBO
From $417 per night (USD)
Expedia
Old Town main house and guest house one block from Duval Street for the best of Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This luxury Old Town renovation is on a quiet end of Virginia street with no through traffic but located only one block ...
From $417 per night (USD)
Expedia
From $1331 per night (USD)
VRBO
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Tranquility. ...
From $1331 per night (USD)
VRBO
$Key Haven 3bedroom 2bath canal front home w\/boat dock, private pool, parking$
From $262 per night (USD)
Expedia
Key Haven 3bedroom 2bath canal front home w\/boat dock, private pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $262 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Endless Sunset Views, Endless Comfort: Explore Our Remodeled Bayfront Condo!
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
60 day minimum rental required. Recently renovated 2 bedrooms and 2.5 baths unit overlooking the Bay. Enjoy the Key Larg ...
From $284 per night (USD)
VRBO
From $530 per night (USD)
VRBO
Bohemian Retreat with Pool in Old Town Key West | Walk to Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $530 per night (USD)
VRBO
From $652 per night (USD)
VRBO
Stylish and Modern 2BR Suite Near Old Town | Pool + Patio
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $652 per night (USD)
VRBO
From $627 per night (USD)
VRBO
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $627 per night (USD)
VRBO
From $710 per night (USD)
VRBO
Escape to Key West: Stylish Boutique Hotel by Duval Street | Pool & Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $710 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Garden-Set Bungalows Featuring Poolside Bliss- Near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $529 per night (USD)
VRBO
From $508 per night (USD)
VRBO
Romantic Getaway: Sun-Drenched Bungalows near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $508 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools Near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $465 per night (USD)
VRBO
From $546 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $546 per night (USD)
VRBO
From $542 per night (USD)
VRBO
Tropical Escape: Artistic-Vibe Bungalows Steps from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $542 per night (USD)
VRBO
From $584 per night (USD)
VRBO
Enchanting Hideaway Perfect for Couples Seeking Romantic Bliss
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $584 per night (USD)
VRBO
From $455 per night (USD)
VRBO
Serene Bungalow in Key West: Poolside Refreshers & Relaxing Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $455 per night (USD)
VRBO
From $517 per night (USD)
VRBO
Unwind in Paradise: Playful Historic Bungalows with Resort-Like Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $517 per night (USD)
VRBO
From $798 per night (USD)
VRBO
Coastal Bliss: Tranquil Bungalows with an Artistic Vibe in Vibrant Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $798 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Seaside Retreat: Inviting Bungalows with Turkish Robes and Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $531 per night (USD)
VRBO
From $624 per night (USD)
VRBO
Stunning Hideaway: Charming Bungalows near Ernest Hemingway Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $624 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Historic Inn: Romantic Stay in Key West's Hidden Gem - Pools & Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $521 per night (USD)
VRBO
From $2226 per night (USD)
VRBO
Oceanfront Retreat: Daily Housekeeping, Fitness Center Access, Latin Cuisine
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2226 per night (USD)
VRBO
From $2285 per night (USD)
VRBO
Tropical Paradise: Daily Housekeeping, Tiki Bar, On-Site Restaurant
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2285 per night (USD)
VRBO
From $1593 per night (USD)
VRBO
Island Serenity: Private Balcony, On-Site Dining, 3 Pools
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1593 per night (USD)
VRBO
From $151 per night (USD)
VRBO
Island Time in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
NEW UNIT! Summer and Fall DiscountsGo back in “Island” Time, located in the historic Wilhelmina Harvey house, who was th ...
From $151 per night (USD)
VRBO
$Pelican Perch: updated 2bed\/2ath beachfront condo with shared pool$
From $322 per night (USD)
Expedia
Pelican Perch: updated 2bed\/2ath beachfront condo with shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Pelican Perch! This meticulously crafted 2-bedroom, 2-bathroom condo offers an unparalleled blend of luxury ...
From $322 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Bayfront Townhome with Boat Slip, Pool and Beach
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
PROPERTY NAME: Seas The Day 88540 Overseas Highway TH#701, Plantation Key, Florida LOCATION: End unit townhouse on the ...
From $521 per night (USD)
VRBO
From $619 per night (USD)
VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $619 per night (USD)
VRBO
From $710 per night (USD)
VRBO
Palms and Pool Paradise
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to our luxurious Key West retreat in the heart of midtown! This spacious house boasts a private pool, soothing h ...
From $710 per night (USD)
VRBO
From $394 per night (USD)
VRBO
Escape to the Keys! Modern Pet-friendly Unit! EV Charger and Parking! Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $394 per night (USD)
VRBO
$Seaside Serenity-2bed 2bath renovated monthly condo w\/ pool, tennis court$
From $216 per night (USD)
VRBO
Seaside Serenity-2bed 2bath renovated monthly condo w\/ pool, tennis court
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $216 per night (USD)
VRBO
From $628 per night (USD)
Expedia
Updated Old Town condo with pool & parking 5 min walk to Duval and Truman Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This gorgeous 2-bedroom, 2-bathroom unit offers a slice of Key West paradise within a gated property, ensuring security ...
From $628 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Cozy Airstream Bambi- in Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover unforgettable moments in our Airstream Bambi at Sun Outdoors Marathon, located in the beautiful Florida Keys. N ...
From $228 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Cozy Airstream Bambi- at Resort on Bayside
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover unforgettable moments in our Airstream Bambi at Sun Outdoors Marathon, located in the beautiful Florida Keys. N ...
From $182 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Dog-friendly duplex with a furnished patio & fast WiFi - near beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tropical Treat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $446 per night (USD)
VRBO
From $1878 per night (USD)
VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1878 per night (USD)
VRBO
From $763 per night (USD)
VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $763 per night (USD)
VRBO
From $486 per night (USD)
VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $486 per night (USD)
VRBO
From $763 per night (USD)
VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $763 per night (USD)
VRBO
From $831 per night (USD)
VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $831 per night (USD)
VRBO
From $468 per night (USD)
VRBO
Family-Friendly Key West Resort with Private Beach on Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $468 per night (USD)
VRBO
From $889 per night (USD)
VRBO
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $889 per night (USD)
VRBO

Search Your Destination Now!

Florida Keys Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals