Florida Keys Rentals
- From $591 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 $591 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 $237 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 $237 per night (USD)VRBO
- From $1125 per night (USD)
Expedia
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 $1125 per night (USD)Expedia
- From $416 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 $416 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 PricingExpedia
- From $207 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 $207 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 $574 per night (USD)
VRBO
Discover paradise in this bay view tropical oasis for the perfect Keys gateway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The space We want to go above and beyond to provide an amazing stress-free vacation and experience that accommodates to ...
From $574 per night (USD)VRBO
- From $444 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 $444 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 $589 per night (USD)
Expedia
KCB ~ Aqua Vista ~ Luxury Waterfront Oasis with Pool and Dock!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
KCB ~ Aqua Vista Welcome to Aqua Vista, your ideal vacation retreat located in the heart of Key Colony Beach! This exqu ...
From $589 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 $863 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 $863 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 $265 per night (USD)
Expedia
Book now for October and enjoy Fantasy Fest and the famous Goombay Festival.
- 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 $265 per night (USD)Expedia
- From $1637 per night (USD)
VRBO
Paraiso Del Mar ~ Luxury Tropical Oasis w\/ Private Pool & 35` Dock!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Paraíso Del Mar Introducing our newest luxury vacation rental nestled in the prestigious community of Marathon. This br ...
From $1637 per night (USD)VRBO
- From $655 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 $655 per night (USD)Expedia
- From $756 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 $756 per night (USD)VRBO
- From $242 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 $242 per night (USD)Expedia
- From $314 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 $314 per night (USD)VRBO
- From $866 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 $866 per night (USD)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)
VRBO
Beautiful Home in Marathon, In the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Water views from main area, and b ...
From $363 per night (USD)VRBO
- From $289 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 $289 per night (USD)VRBO
- From $907 per night (USD)
Expedia
Villa Franchella ~ Luxury Waterfront Pool Home, Mins from the Gulf! 45` Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Villa Franchella Escape to paradise and experience the epitome of luxury living in this new breathtaking 4-bedroom, 3-b ...
From $907 per night (USD)Expedia
- 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
- From $297 per night (USD)
Expedia
Little Venice Paradise~55` dock access to Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Little Venice Paradise Escape to paradise with this charming two-bedroom, two-bathroom canal-front vacation rental home ...
From $297 per night (USD)Expedia
- From $1090 per night (USD)
VRBO
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 $1090 per night (USD)VRBO
- From $658 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 $658 per night (USD)Expedia
- From $304 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 $304 per night (USD)VRBO
- From $1005 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
A fun and modern 4-bedroom home with an Instagram photo wall, turf screened in backyard and fully appointed kitchen with ...
From $1005 per night (USD)Expedia
- From $335 per night (USD)
VRBO
Sandpiper Cove: updated 2bed\/2bath beachfront condo with shared pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sandpiper Cove - your exclusive beachfront sanctuary! This impeccably designed 2-bedroom, 2-bathroom condo i ...
From $335 per night (USD)VRBO
- From $2246 per night (USD)
VRBO
Old Town Key West Retreat | Seaport Paradise Room with Pool Access | 3 Rooms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2246 per night (USD)VRBO
- From $749 per night (USD)
VRBO
Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $749 per night (USD)VRBO
- From $2995 per night (USD)
VRBO
Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2995 per night (USD)VRBO
- From $7265 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 $7265 per night (USD)VRBO
- From $3170 per night (USD)
VRBO
Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3170 per night (USD)VRBO
- From $1497 per night (USD)
VRBO
Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1497 per night (USD)VRBO
- From $4029 per night (USD)
VRBO
2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $4029 per night (USD)VRBO
- From $2378 per night (USD)
VRBO
Seaport Paradise Room with Pools | Old Town Key West Retreat | 3 Rooms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2378 per night (USD)VRBO
- From $793 per night (USD)
VRBO
Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $793 per night (USD)VRBO
- From $3808 per night (USD)
VRBO
Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3808 per night (USD)VRBO
- From $4029 per night (USD)
VRBO
Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $4029 per night (USD)VRBO
- From $1585 per night (USD)
VRBO
Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1585 per night (USD)VRBO
- From $525 per night (USD)
Expedia
Oceanfront condo with large balcony, direct beach access, nautical theme, & W\/D
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
The Turquoise Turtle #30 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $525 per night (USD)Expedia
- From $304 per night (USD)
VRBO
Snowbird-friendly condo in oceanfront complex with heated pool, BBQ, W\/D, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overseas Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $304 per night (USD)VRBO
- From $497 per night (USD)
Expedia
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)Expedia
- From $546 per night (USD)
VRBO
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 $546 per night (USD)VRBO
- From $195 per night (USD)
Expedia
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)Expedia
- From $468 per night (USD)
VRBO
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 $468 per night (USD)VRBO
- From $565 per night (USD)
Expedia
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 $565 per night (USD)Expedia
- Click For Pricing
Expedia
Welcome to Villa Hodali
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience a luxurious stay in our newly renovated 3-bedroom, 2.5-bathroom townhome at Executive Bay Club. Centrally loc ...
Click For PricingExpedia
- From $279 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 $279 per night (USD)Expedia
- From $1018 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 $1018 per night (USD)VRBO
- From $362 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 $362 per night (USD)Expedia
- From $256 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 $256 per night (USD)VRBO
- From $1047 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 $1047 per night (USD)VRBO
- From $1288 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 $1288 per night (USD)VRBO
- From $1116 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 $1116 per night (USD)VRBO
- From $1197 per night (USD)
VRBO
Escape to Key West: Stylish Boutique Hotel by Duval Street | Pool & Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $1197 per night (USD)VRBO
- From $693 per night (USD)
VRBO
Historic Haven w\/ Unique Rooms, Afternoon Refreshers & Steps from Duval St
- 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 $693 per night (USD)VRBO
- From $960 per night (USD)
VRBO
Celebrate History in Key West: Relaxing Bungalows with Resort-Like Amenities
- 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 $960 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 $938 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 $938 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 $799 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 $799 per night (USD)VRBO
- From $931 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 $931 per night (USD)VRBO
- From $996 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 $996 per night (USD)VRBO
- From $694 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 $694 per night (USD)VRBO
- From $923 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 $923 per night (USD)VRBO
- From $1173 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 $1173 per night (USD)VRBO
- From $901 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 $901 per night (USD)VRBO
- From $1040 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 $1040 per night (USD)VRBO
- From $908 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 $908 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Seaside Serenity-2BD 2BA condo w\/ pool, parking, tennis courts, near beaches
- 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 $263 per night (USD)Expedia
- From $628 per night (USD)
VRBO
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)VRBO
- From $227 per night (USD)
Expedia
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 $227 per night (USD)Expedia
- From $184 per night (USD)
VRBO
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 $184 per night (USD)VRBO
- From $315 per night (USD)
Expedia
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 $315 per night (USD)Expedia
- From $3157 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 $3157 per night (USD)VRBO
- From $1004 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 $1004 per night (USD)VRBO
- From $756 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 $756 per night (USD)VRBO
- From $980 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 $980 per night (USD)VRBO
- From $984 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 $984 per night (USD)VRBO
- From $699 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 $699 per night (USD)VRBO
- From $1122 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 $1122 per night (USD)VRBO
- From $1004 per night (USD)
VRBO
Relaxing Key West Haven with Full-Service Spa and Legendary Dining
- 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 $1004 per night (USD)VRBO
- From $756 per night (USD)
VRBO
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
- 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 $756 per night (USD)VRBO
- From $2536 per night (USD)
VRBO
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2536 per night (USD)VRBO
- From $3747 per night (USD)
VRBO
3 Charming Resort Stays with Private Beach & Spa Treatments - Key West Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $3747 per night (USD)VRBO
- From $1675 per night (USD)
VRBO
2 Traditional Two Queen, Pier House Resort, Beachside, Key West Vibe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1675 per night (USD)VRBO
- From $1069 per night (USD)
VRBO
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
- 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 $1069 per night (USD)VRBO
- From $2468 per night (USD)
VRBO
2 Oceanfront Two Queen, Pier House Resort, Beach Access, Pet-Friendly, Duval St.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2468 per night (USD)VRBO
- From $889 per night (USD)
VRBO
Key West Beachfront Accommodation - Ideal for Family Vacation Fun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
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
- From $1474 per night (USD)
VRBO
2 Serene Beachside Accommodations with Enhanced Spa Experience in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1474 per night (USD)VRBO
- From $2161 per night (USD)
VRBO
2 Sophisticated Resort Rooms Perfect for Family Relaxation! Spa Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2161 per night (USD)VRBO
- From $856 per night (USD)
VRBO
Traditional King, Pier House, Classic Island Style, Fine Dining, Duval Street Proximity
- 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 $856 per night (USD)VRBO
- From $796 per night (USD)
VRBO
Pure Wellness Spa Junior Suite, Pier House, Private Beach Access, Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $796 per night (USD)VRBO
- From $836 per night (USD)
VRBO
Beachfront Bliss with Water Activities & Next to Vibrant Nightlife Attractions
- 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 $836 per night (USD)VRBO