Fleming Key Rentals
- From $816 per night (USD)
VRBO
Tropical Escape! 2 Spacious Units, 3 Pools!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $816 per night (USD)VRBO
- From $2648 per night (USD)
VRBO
Perfect Vacation, 3 Spacious Units, Pools, Tiki Bar, Bike Rentals, Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2648 per night (USD)VRBO
- Click For Pricing
VRBO
Best Vacation Ever! 2 Spacious Suites for 8, Pools, Tiki Bar, Gym, Bike Rentals!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $212 per night (USD)
Expedia
Sailboat ⛵️
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy Beautiful Views of Key West Harbor and unforgettable Sunsets aboard your own private Sailing Yacht.. Fresh hot/co ...
From $212 per night (USD)Expedia
- From $243 per night (USD)
VRBO
Old Town Oasis - Sleeps 4, Steps to Duval and Beaches.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Treetop Cottage is located in the heart of old town, walking distance to all the shops, restaurants and attractions of D ...
From $243 per night (USD)VRBO
- Click For Pricing
Expedia
The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from Duval St & Seaport!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Pinder House, where modern comfort meets historic charm in the heart of Old Town Key West. This beautiful ...
Click For PricingExpedia
- From $1072 per night (USD)
VRBO
A Palm Tree Haven in Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cu ...
From $1072 per night (USD)VRBO
- From $1428 per night (USD)
Expedia
Conch House in Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Quintessential Grand Key West Estate! The James J. Curtis House c. 1874 was acquired by the Navy in 1903 and the home b ...
From $1428 per night (USD)Expedia
- From $113 per night (USD)
VRBO
Cubana Casita in Key West
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Cubana Casita is an easy-access ground floor condo with one bedroom and 1½ baths. This special home's 'from the ground u ...
From $113 per night (USD)VRBO
- From $150 per night (USD)
Expedia
The Sea Glass Cottage in Historic Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spend time in beautiful Key West and live like a local in a true Conch Home! The Sea Glass Cottage is perfect for group ...
From $150 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Priced to book! 2 Bdr\/2Ba Walking distance to Duval St., Mallory Square, Trolley
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
From $465 per night (USD)VRBO
- From $482 per night (USD)
Expedia
DOWNTOWN KEY WEST 2BED OCEANFRONT!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a great OCEANFRONT unit with large balcony to watch sunsets. Hyatt Sunset Harbor is perfectly located in downtow ...
From $482 per night (USD)Expedia
- Click For Pricing
VRBO
Dream Getaway! 4 Modish Units, Pools, Restaurant with Latin Cuisine, Bar!
- 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 ...
Click For PricingVRBO
- From $205 per night (USD)
Expedia
Underwater Cabana at Custom House Inn | On Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to Underwater Cabana at the Custom House Inn! Each apartment in our five unit complex is uniquely desig ...
From $205 per night (USD)Expedia
- From $322 per night (USD)
VRBO
Citrus Queen at Custom House Inn | On Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to Citrus Queen at the Custom House Inn! Each apartment in our five unit complex is uniquely designed a ...
From $322 per night (USD)VRBO
- From $205 per night (USD)
Expedia
Chicken Run at Custom House Inn | On Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to Chicken Run at the Custom House Inn! Each apartment in our five unit complex is uniquely designed an ...
From $205 per night (USD)Expedia
- From $524 per night (USD)
VRBO
Partial Harbor View King at The Marker Waterfront Resort Key West
- 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 $524 per night (USD)VRBO
- From $490 per night (USD)
VRBO
Perfect Location to Key West Action! Pools, Onsite Restaurant\/Bar, Bike Rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $490 per night (USD)VRBO
- From $387 per night (USD)
VRBO
Beach Escapade! Pools, Restaurant & Bar, 2 Blocks Away from Famous Duval Street
- 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 $387 per night (USD)VRBO
- From $440 per night (USD)
VRBO
Key West At It's Best! 3 Pools, Tiki Bar, Bike Rentals, Onsite Restaurant!
- 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 $440 per night (USD)VRBO
- From $1676 per night (USD)
VRBO
Amazing Getaway Location! 4 Modish Units, 3 Pools, Onsite Restaurant, Tiki Bar!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1676 per night (USD)VRBO
- From $529 per night (USD)
VRBO
Pool & Garden View King at The Marker Waterfront Resort Key West
- 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 $529 per night (USD)VRBO
- From $1905 per night (USD)
VRBO
4 x The Marker Classic 2 Queens at The Marker Waterfront Resort Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1905 per night (USD)VRBO
- From $441 per night (USD)
VRBO
Tropical Getaway! 3 Pools, Restaurant & Bar, 2 Blocks Away from Duval Street!
- 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 $441 per night (USD)VRBO
- From $472 per night (USD)
VRBO
Paradise Escape! 3 Pools, Restaurant with Latin Cuisine, Tiki Bar, Cycling!
- 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 $472 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Perfect Escape! Pools, Onsite Restaurant & Bar, Bike Rental, Pets Allowed!
- 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 $600 per night (USD)VRBO
- From $683 per night (USD)
VRBO
Fantastic Stay, Best Location! 3 Pools, Restaurant with Latin Cuisine, Dining!
- 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 $683 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Key West At It's Best! 3 Pools, Restaurant & Bar, Bike Rental, Pet-friendly!
- 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 $465 per night (USD)VRBO
- From $408 per night (USD)
VRBO
The Marker Classic 2 Queen Beds at The Marker Waterfront Resort Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $408 per night (USD)VRBO
- From $537 per night (USD)
VRBO
Wonderful Beach Vacation! Pool, Onsite Restaurant & Bar, Parking, Bike Rental
- 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 $537 per night (USD)VRBO
- From $1436 per night (USD)
VRBO
3 x The Marker Classic 2 Queens at The Marker Waterfront Resort Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1436 per night (USD)VRBO
- From $1196 per night (USD)
VRBO
3 Spacious Units Great For Family Getaways Minutes From The Beach! Cycling!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
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 $1962 per night (USD)
VRBO
2 x Marker Residences One Bedroom at The Marker Waterfront Resort Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1962 per night (USD)VRBO
- From $2282 per night (USD)
VRBO
Dream Vacation! 2 Spacious Units, 3 Pools, Restaurant & Bar, Bike Rental!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2282 per night (USD)VRBO
- Click For Pricing
VRBO
2 x Serenity Suite - One Bedroom Accessible at The Marker Waterfront Resort Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- Click For Pricing
VRBO
Tropical Getaway! 2 Spacious Suites for 8, 3 Pools, Bike Rental, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $497 per night (USD)
VRBO
Perfect Location to Key West Action! Pools, Restaurant & Bar, Cycling, Pool View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $497 per night (USD)VRBO
- From $463 per night (USD)
VRBO
Classic King at The Marker Waterfront Resort Key West
- 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 $463 per night (USD)VRBO
- Click For Pricing
VRBO
4 x Serenity Suite - One Bedroom ADA at The Marker Waterfront Resort Key West
- 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 ...
Click For PricingVRBO
- From $978 per night (USD)
VRBO
2 x The Marker Classic 2 Queens at The Marker Waterfront Resort Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $978 per night (USD)VRBO
- From $509 per night (USD)
VRBO
Pool Garden View Balcony 2 Queens at The Marker Waterfront Resort Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $509 per night (USD)VRBO
- From $905 per night (USD)
VRBO
Close to Attractions! 2 Modern Units, Pools, Pets Allowed, Onsite Restaurant!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $905 per night (USD)VRBO
- From $923 per night (USD)
VRBO
Wonderful Beach Vacation! 3 Pools, Restaurant & Bar, Bike Rental, Pets Allowed!
- 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 $923 per night (USD)VRBO
- Click For Pricing
VRBO
Amazing Stay, Great Location! 2 Spacious Units, Restaurant with Latin Cuisine
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- Click For Pricing
VRBO
Amazing Stay, Great Location! 2 Modish Units, 3 Pools, Bike Rental, Pets Allowed
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $923 per night (USD)
VRBO
Fantastic Stay, Best Location! Harbor View and Terrace, Bike Rental, Dining!
- 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 $923 per night (USD)VRBO
- Click For Pricing
VRBO
Best Vacation, 4 Spacious Units, Bar, Pools, Tiki Bar, Bike Rentals, Parking!
- 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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
Great Location! 3 Spacious Units, Pools, Pet-friendly, Restaurant & Bar!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $895 per night (USD)
VRBO
Tropical Experience! Pools, Restaurant with Latin Cuisine, Cycling, Pet-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $895 per night (USD)VRBO
- Click For Pricing
VRBO
Key West At It's Best! 3 Modish Units, 3 Pools, Tiki Bar, Pets Allowed, Cycling!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- Click For Pricing
VRBO
Best Vacation Ever! 4 Modish Units! 3 Pools, Restaurant with Latin Cuisine!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- Click For Pricing
VRBO
Ultimate Vacay! 4 Modern Units, Pools, Fitness Center, Restaurant, Bar, Parking!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- Click For Pricing
VRBO
Tropical Getaway! 3 Modish Units, 3 Pools, Bike Rentals, Onsite Restaurant!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $882 per night (USD)
VRBO
Perfectly Located to Everything! Pool, Tiki Bar, Bike Rental, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $882 per night (USD)VRBO
- From $946 per night (USD)
VRBO
Beach Escapade! Pools, Restaurant & Bar, 2 Blocks Away from Famous Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $946 per night (USD)VRBO
- From $932 per night (USD)
VRBO
Look No Further! 3 Pools, Restaurant, Tiki Bar, Bike Rental, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $932 per night (USD)VRBO
- From $3976 per night (USD)
VRBO
4 Tropical Units, 3 Pools, Fitness Center, On-site Restaurant & Bar, Parking!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $3976 per night (USD)VRBO
- From $3601 per night (USD)
VRBO
Dream Getaway, 4 Tropical Units, 3 Pools, Tiki Bar, Bike Rentals, Parking!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $3601 per night (USD)VRBO
- Click For Pricing
VRBO
Amazing Vacation! 3 Spacious Units! 3 Pools, Restaurant, Tiki Bar, Bike Rental!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- Click For Pricing
VRBO
Luxurious Vacation! 4 Snug Units, Pools, Tiki Bar, Bike Rentals, Parking!
- 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 ...
Click For PricingVRBO
- From $3777 per night (USD)
VRBO
4 x Marker Residences One Bedroom Suite at The Marker Waterfront Resort Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $3777 per night (USD)VRBO
- Click For Pricing
Expedia
Best Location in Key West-Hyatt Sunset Harbor with water view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
LISTING is ONLY available January 29 to Feb 5. Best location in town. Only 1.5 blocks to Duvall Street but quiet. Key We ...
Click For PricingExpedia
- From $275 per night (USD)
VRBO
Sunshine State at Custom House Inn | On Duval!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to Sunshine at the Custom House Inn! Each apartment in our five unit complex is uniquely designed and t ...
From $275 per night (USD)VRBO
- From $267 per night (USD)
Expedia
The Caroline #2 | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We are proud to present completely remodeled historic house build in 1928. The Bayview house features 4 units. unit is ...
From $267 per night (USD)Expedia
- From $133 per night (USD)
VRBO
Truman's Treasure: Beautifully Updated 2nd Floor Condo, Perfectly Convenient to Duval St & Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Truman's Treasure," where you can fully embrace the vibrant and unique Key West lifestyle. This beautifully ...
From $133 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Airy & Bright Home with Pool in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect getaway for a long stay in Key West. A private pool and patio area lie behind a green gate on a quiet lane i ...
From $200 per night (USD)VRBO
- From $455 per night (USD)
VRBO
~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $455 per night (USD)VRBO
- Click For Pricing
Expedia
Hyatt Residence Club Sunset Harbor-Old Town- Heart of Key West, Sleeps 4!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical Key West welcomes you to a classic Florida condominium, offering a one bedroom unit with plush queen bed, fully ...
Click For PricingExpedia
- From $743 per night (USD)
VRBO
Stunning Views at The Galleon Resort in Beautiful Key West! Charming 2 Bed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
These are 7-night rentals, with check-in on Saturdays only. Overlooking the shimmering span of Gulf of Mexico in histor ...
From $743 per night (USD)VRBO
- From $213 per night (USD)
Expedia
Ultimate Escape-2 bed 2 bath Old Town home, parking, open layout, Mid-century
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $213 per night (USD)Expedia
- From $439 per night (USD)
VRBO
**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE GILDED PI ...
From $439 per night (USD)VRBO
- Click For Pricing
Expedia
Windsor Townhome #5- 3 bedroom 3.5 bath with private pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently ...
Click For PricingExpedia
- Click For Pricing
Expedia
Beautiful 2 Bedroom Penthouse with Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A beautiful penthouse condo located right off the marina in the heart of Old Town Key West. Take a nice morning stroll a ...
Click For PricingExpedia
- From $91 per night (USD)
VRBO
Adorable gated loft studio two blocks from Duval in Old Town - Location Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Sanctuary is tucked away on a quiet street just two blocks off Duval St. in Old Town Key West. This hidden gem is on ...
From $91 per night (USD)VRBO
- From $205 per night (USD)
VRBO
Casa Azul by Brightwild|Open Concept, Pool & Pets!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Casa Azul is a luxe modern cottage with an open-concept living area that ends up filled with natural sunlight. ...
From $205 per night (USD)VRBO
- From $204 per night (USD)
Expedia
White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Dog-Friendly Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the best of Key West in the White Ibis, a delightful 2BR home situated in the artistic enclave of the White S ...
From $204 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Hot tin roof on Olivia Street, Key West Florida
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located right across from the cemetery in the heart of old town Key West this property is in the perfect location to the ...
From $175 per night (USD)VRBO
- Click For Pricing
Expedia
Conch Out Cottage super close to Duval Street Entertainment area
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Timeless Two bedroom Key West Cottage located in Olde Town four blocks from Duval Street entertainment district. From th ...
Click For PricingExpedia
- From $599 per night (USD)
VRBO
The Bungalow at Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our exclusive One Bedroom bungalow features a relaxing ambience for honeymooners and couples. The overall concept of the ...
From $599 per night (USD)VRBO
- From $1418 per night (USD)
Expedia
2-Bedroom Suite at a 4⭐️ Hotel
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Approximately 1,200 square feet, King bed in Master, Queen bed in second bedroom, Living area with Queen sleeper sofa an ...
From $1418 per night (USD)Expedia
- From $185 per night (USD)
VRBO
The Cozy Little Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Cozy Little Cottage !!! A REAL ISLAND GATAWAY IN KEY WEST!!! Nested in the heart of Key West, The Cozy L ...
From $185 per night (USD)VRBO
- From $1728 per night (USD)
VRBO
\"Big Blu\" is a 5-bed, 4-bath home with a heated pool in downtown Key West.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
NEW ON THE RENTAL MARKET - Big Blu is a recently renovated five-bedroom, four-bathroom traditional shotgun house with a ...
From $1728 per night (USD)VRBO
- From $410 per night (USD)
VRBO
Old Town Carey Lane Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated ...
From $410 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Frogmore on Fleming in Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your dream residence in the heart of Key West, Florida! Nestled in a prime location, this 2-bedroom apartment ...
From $450 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Airy & Bright Home with Pool in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect getaway for a long stay in Key West. A private pool and patio area lie behind a green gate on a quiet lane i ...
From $200 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Large 1 bedroom condo in the historic area of Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy your Key West vacation in this spacious 623 square foot condo located on the second floor of this classical reviva ...
From $125 per night (USD)Expedia
- From $500 per night (USD)
VRBO
PAGITT HOUSE - 3\/ 2 - OLD TOWN KEY WEST WITH POOL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
NEW LISTINGS APRIL - 2024! Welcome to the Pagitt House built in 1933 and located on Elizabeth Street just steps to all ...
From $500 per night (USD)VRBO
- From $1418 per night (USD)
Expedia
2-Bedroom Suite at a 4⭐️ Hotel
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Approximately 1,200 square feet, King bed in Master, Queen bed in second bedroom, Living area with Queen sleeper sofa an ...
From $1418 per night (USD)Expedia
- From $239 per night (USD)
VRBO
KALI ZOI HOUSE ~ Charming 3 BR\/3 Ba Home in Old Town w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
THE GOOD LIFE AWAITS... Kali Zoi is Greek for 'good life" and that is what you'll experience in this island retreat in t ...
From $239 per night (USD)VRBO
- From $699 per night (USD)
VRBO
NEW! ~ K2escape ~ One of a kind tropical piece of paradise!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The k2 escape is the very best in indoor/ outdoor living. The full size heated pool is surrounded by lush mature tropica ...
From $699 per night (USD)VRBO
- From $296 per night (USD)
VRBO
Conch Cottage Retreat in the heart of Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Experience Old Town Key West in a classic conch home! This home is only steps from shopping, restaurants, the historic s ...
From $296 per night (USD)VRBO
- From $455 per night (USD)
Expedia
Two fully independent units in a Duplex, with independent entrances. One Rent!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to "Old Key West". Our Classic Old Town style duplex, with two independent fully renovated homes in the same pro ...
From $455 per night (USD)Expedia
- From $1200 per night (USD)
VRBO
ELIZABETH'S SECRET: 3\/2 In Old Town Key West, with a Private pool and Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Elizabeth's Secret! You have found your secret! A very private and secluded tropical oasis awaits you behin ...
From $1200 per night (USD)VRBO
- From $385 per night (USD)
Expedia
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w\/ Pool, Spa & Exercise Room!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
OLD TOWN CLASSIC... This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding loc ...
From $385 per night (USD)Expedia
- From $213 per night (USD)
VRBO
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Retreat Centrally Located w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WHERE LIFE IS PURE… This dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West c ...
From $213 per night (USD)VRBO
- From $110 per night (USD)
Expedia
THE HIDDEN GEM ~ Charming Renovated Studio with Large Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
HIDDEN GARDEN STUDIO… This charming 340 sq.ft. escape in the exclusive Lionsgate Condominium community will delight your ...
From $110 per night (USD)Expedia
- From $114 per night (USD)
VRBO
524 Elizabeth St. #2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located place. Located just blocks from duval and many of it's restaurants ...
From $114 per night (USD)VRBO
- From $303 per night (USD)
Expedia
613 Fleming. St. Unit 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Great location in the heart of it all. Short walk to Duval Street, bars, shops and restaurants. Quiet enough to have a p ...
From $303 per night (USD)Expedia
- From $476 per night (USD)
VRBO
The Leonella, Old Town Key West.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Leonella is an Imaginative and impeccable restoration of a Key West conch house mixing contemporary style and histor ...
From $476 per night (USD)VRBO
- From $795 per night (USD)
VRBO
SEAPORT PANORAMA at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...
From $795 per night (USD)VRBO