Key West Rentals
- From $277 per night (USD)
VRBO
Hidden Gem In Tropical Key West! Stay Just Minutes Away From The Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $277 per night (USD)VRBO
- From $275 per night (USD)
VRBO
You Found it! Amazing Room w\/ 2 Queen Beds, Outdoor Swimming Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $275 per night (USD)VRBO
- From $549 per night (USD)
VRBO
You Found it! Two Amazing Rooms w\/ (2 Queen Beds Each), Outdoor Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $549 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Fantastic Land and Sea Vacation! Two Convenient Rooms, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $625 per night (USD)VRBO
- From $327 per night (USD)
VRBO
Perfect Staycation for Family & Friends! Premium Ocean View Room, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $327 per night (USD)VRBO
- From $252 per night (USD)
VRBO
Perfect Location for Your Staycation! Spacious Deluxe Room w\/ Pool View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $252 per night (USD)VRBO
- From $523 per night (USD)
VRBO
Perfect Staycation! 2 Spacious Rooms, Close to Local Attractions & Shopping
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $523 per night (USD)VRBO
- From $607 per night (USD)
VRBO
Ideal Location! Two Relaxing Rooms, Outdoor Pool, Minutes Away from the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $607 per night (USD)VRBO
- From $554 per night (USD)
VRBO
Perfect Staycation! Two Amazing Pool View Units, Close to County Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $554 per night (USD)VRBO
- From $277 per night (USD)
VRBO
Perfect staycation! Close to Smathers Beach, Outdoor Recreation! Onsite Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $277 per night (USD)VRBO
- From $319 per night (USD)
VRBO
Fantastic Land and Sea Vacation! Onsite Pool, Close to Nearest Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $319 per night (USD)VRBO
- From $280 per night (USD)
VRBO
Amazing Stay in the Keywest! Deluxe Pool View Two Queen Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $280 per night (USD)VRBO
- From $832 per night (USD)
VRBO
Fantastic Land and Sea Vacation! 3 Convenient Units, Onsite Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $832 per night (USD)VRBO
- From $292 per night (USD)
VRBO
Fantastic Land and Sea Vacation! Amazing Ocean View Room w\/ King Bed, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $292 per night (USD)VRBO
- From $349 per night (USD)
VRBO
Panoramic Ocean View! Amazing Room w\/ King Bed, Outdoor Swimming Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $349 per night (USD)VRBO
- From $247 per night (USD)
VRBO
Fantastic Land and Sea Vacation! Outdoor Pool, Short Drive To The Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $247 per night (USD)VRBO
- From $526 per night (USD)
VRBO
Ideal Location for Your Next Getaway! 2 Spacious Rooms, Outdoor Swimming Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $526 per night (USD)VRBO
- From $288 per night (USD)
VRBO
Ideal Location! Near County Beach, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $288 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Perfect Staycation! Outdoor Recreation, Minutes Away from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $261 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Fantastic Land and Sea Vacation! Amazing Room w\/ 2 Queen Beds, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $275 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Waterfront Key West home w\/Pool & Hot Tub on Riveria canal!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Large 3 Bedroom / 2 Bath private residence with in-ground pool and hot tub located directly on the Riviera Canal in bea ...
From $450 per night (USD)VRBO
- From $458 per night (USD)
VRBO
Your Exciting Florida Vacation Starts Here! Ocean View, 3 Pools, Nightlife!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $458 per night (USD)VRBO
- From $428 per night (USD)
VRBO
You Found it! Key West Getaway! Oceanfront Pool, Onsite Dining, Bike Rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $428 per night (USD)VRBO
- From $522 per night (USD)
VRBO
Oceanfront and Adult Only Pool, Bike Rental, Beach Bar, Near Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $522 per night (USD)VRBO
- From $1256 per night (USD)
VRBO
Authentic Florida Experience! 3 Modern Units, Oceanfront Pool, Beach Access!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1256 per night (USD)VRBO
- Click For Pricing
Expedia
Robinson Crusoe Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Robinson Crusoe Cottage is a one beroom cottage with queen bed, sleeper sofa, kitchen and private bath. The queen bed s ...
Click For PricingExpedia
- From $505 per night (USD)
VRBO
Welcome to a Sun-Soaked Paradise! 3 Pools, Beach Bar, Nightlife, Onsite Dining!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $505 per night (USD)VRBO
- From $419 per night (USD)
VRBO
Paradise Getaway! Bike Rental, 3 POOLS, Bar, Short Walk to Southernmost Point!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $419 per night (USD)VRBO
- From $1639 per night (USD)
VRBO
Steps From The Sand! 3 Modern Units, Ocean Views, Pool, Bike Rental, Nightlife
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1639 per night (USD)VRBO
- From $1489 per night (USD)
VRBO
Beach Stay 3 Comfortable Units, 3 Onsite Pools & Onsite Spa, Near Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1489 per night (USD)VRBO
- From $993 per night (USD)
VRBO
Get Ready for Your Florida Adventure! 2 Modish Units Onsite Dining, Bike Rental!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $993 per night (USD)VRBO
- From $837 per night (USD)
VRBO
Laidback Oceanfront Bar and Recreation Area! 2 Convenient Units, Onsite Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $837 per night (USD)VRBO
- From $414 per night (USD)
VRBO
Superior King ADA Accommodation at Southernmost Beach Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $414 per night (USD)VRBO
- From $605 per night (USD)
VRBO
Superior 2 Queen Beds Room at Southernmost Beach Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $605 per night (USD)VRBO
- From $1481 per night (USD)
VRBO
Breathtaking Ocean Views! 3 Trendy Units, On-Site Dining, Near Jackson Square!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1481 per night (USD)VRBO
- From $558 per night (USD)
VRBO
Welcome to Paradise! Discover the History and Soul of Key West! Nightlife!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $558 per night (USD)VRBO
- From $605 per night (USD)
VRBO
Delight In Historic Old Town Key West! Beautiful Stay Minutes From Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $605 per night (USD)VRBO
- From $476 per night (USD)
VRBO
Laidback Oceanfront Bar and Recreation Area! Nightlife, 3 Pools, Beach Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $476 per night (USD)VRBO
- From $250 per night (USD)
VRBO
CLOUD 9 ~ 4 Bedroom, 3.5 Bathroom with Off Street Parking and Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
NO PASSPORT REQUIRED… A lovingly restored island retreat with luxurious coastal flair, this home’s aesthetic beauty draw ...
From $250 per night (USD)VRBO
- From $2185 per night (USD)
VRBO
4 Deluxe 2 Queen Beds Rooms at Southernmost Beach Resort
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $2185 per night (USD)VRBO
- From $906 per night (USD)
VRBO
Your Exciting Florida Vacay Starts Here! 2 Island View Units, Onsite Restaurant
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $906 per night (USD)VRBO
- From $1344 per night (USD)
VRBO
Beachside Dream! 3 Stylish Units, Near Key West Butterfly & Nature Conservatory
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1344 per night (USD)VRBO
- From $232 per night (USD)
VRBO
Royal Poinciana Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Royal Poinciana is a studio cottage with queen bed, kitchen and private bath. The queen bed sleeps 2 people and the kit ...
From $232 per night (USD)VRBO
- From $527 per night (USD)
VRBO
Welcome to a Sun-Soaked Paradise! Discover the History and Soul of Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $527 per night (USD)VRBO
- From $1021 per night (USD)
VRBO
Great for Family Trips! 2 Modern Units, Pool, Restaurant, Near Jackson Square!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1021 per night (USD)VRBO
- From $1105 per night (USD)
VRBO
2 Deluxe 2 Queen Beds Accommodations at Southernmost Beach Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1105 per night (USD)VRBO
- From $508 per night (USD)
VRBO
Just What You Were Looking For! 3 Pools, Onsite Spa, Near Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $508 per night (USD)VRBO
- From $1792 per night (USD)
VRBO
Private Tanning Pier! 4 Modern Units By The Beach, 3 Onsite Pools, Beach Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1792 per night (USD)VRBO
- From $1619 per night (USD)
VRBO
Duval Street where Old Town meets the Atlantic! 4 Modern Units! Free Onsite Game
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1619 per night (USD)VRBO
- From $390 per night (USD)
VRBO
Outdoor Pool with Ocean View! Nightlife, Bar, Near Jackson Square & Sunset Pier!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $390 per night (USD)VRBO
- From $472 per night (USD)
VRBO
Ultimate Beach Escape! 3 Pools, Bike Rental, Nightlife, Near Jackson Square!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $472 per night (USD)VRBO
- From $368 per night (USD)
VRBO
Deluxe Room with Balcony and King Bed at Southernmost Beach Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $368 per night (USD)VRBO
- From $504 per night (USD)
VRBO
Exciting Tropical Vacation! Nightlife, Beach Access, Walk to Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $504 per night (USD)VRBO
- From $819 per night (USD)
VRBO
Duval Street Where Old Town Meets the Atlantic! 2 Modern Units, 3 Pools, Spa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $819 per night (USD)VRBO
- From $398 per night (USD)
VRBO
Experience Florida Like Never Before! Oceanfront Pool, Nightlife, Beach Bar!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $398 per night (USD)VRBO
- From $147 per night (USD)
VRBO
Pet-Friendly. LOCALS SAVE!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Steps away from Smather's Beach. This is a PET-FRIENDLY 3/2 unit in an exclusive gated community. Great location for a ...
From $147 per night (USD)VRBO
- Click For Pricing
Expedia
Windward Breeze II - 2 Bedroom \/ 2 Bath Townhome Close to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About The Area Windward Breeze is part of the Windward Park gated community just off Simonton Street, one block from Duv ...
Click For PricingExpedia
- From $766 per night (USD)
VRBO
SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
ONLY THE BEST WILL DO… An exceptional opportunity to immerse yourself in island life within this renovated, classic Key ...
From $766 per night (USD)VRBO
- From $511 per night (USD)
VRBO
CASABELLA@DUVAL SQUARE Lovely 2 Bedroom 2.5 Bath Townhome in a great location
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Duval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool a ...
From $511 per night (USD)VRBO
- From $345 per night (USD)
VRBO
Colony Poolside: A charming bungalow near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $345 per night (USD)VRBO
- From $1175 per night (USD)
VRBO
Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool\/Hot Tub & Proximity to the Beach & Duval St!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover Salt Ponds Sanctuary - Your Tranquil Key West Retreat! Escape to the beauty of Key West at Salt Ponds Sanctuary ...
From $1175 per night (USD)VRBO
- From $472 per night (USD)
VRBO
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
STEPS TO IT ALL... Peaceful surroundings of swaying palm trees and picturesque white picket fences invite you in to this ...
From $472 per night (USD)VRBO
- From $232 per night (USD)
VRBO
~ BOHEMIAN HOUSE ~ Come enjoy this well-located, carefree home with a pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $232 per night (USD)VRBO
- From $499 per night (USD)
VRBO
Beach Club #103 - Unique oceanfront living with breathtaking views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $499 per night (USD)VRBO
- From $424 per night (USD)
VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $424 per night (USD)VRBO
- From $187 per night (USD)
VRBO
SEA-NIC VIEW ~ Price reduction for April-May!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a comple ...
From $187 per night (USD)VRBO
- From $1724 per night (USD)
VRBO
Classic Key West Estate
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation re ...
From $1724 per night (USD)VRBO
- From $210 per night (USD)
Expedia
Tropical oasis in a former author’s retreat. Sleeps 4.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Former residence of an author and decorated accordingly, this cute cottage is quintessential Key West. Perfectly maintai ...
From $210 per night (USD)Expedia
- From $156 per night (USD)
VRBO
Pearl in Paradise-Charming 2bed 2bath Old Town home w\/ shared pool, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
xEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and pri ...
From $156 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Duval Square Condo-2 bedroom 2.5 bath, w\/pool, parking, on Duval St
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $475 per night (USD)VRBO
- From $411 per night (USD)
VRBO
Pelican Landing Antigua-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $411 per night (USD)VRBO
- From $424 per night (USD)
VRBO
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes th ...
From $424 per night (USD)VRBO
- From $441 per night (USD)
VRBO
A Slice of Paradise! @ the Shipyard ~ Now 20% off for April & May new bookings!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Old Town, with the beautiful community of private homes and condominiums of Truman Annex, this Shipyard ...
From $441 per night (USD)VRBO
- From $395 per night (USD)
VRBO
2 bdrm Condo w\/ boat slip Pelican Landing Harbor Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $395 per night (USD)VRBO
- Click For Pricing
Expedia
Paradise on Porter- Weekly Rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise on Porter is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West. Th ...
Click For PricingExpedia
- From $864 per night (USD)
VRBO
PINEAPPLE COTTAGE: 2BR\/2BA-Pvt Pool -1\/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $864 per night (USD)VRBO
- From $285 per night (USD)
VRBO
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD\/2.5BA - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. ...
From $285 per night (USD)VRBO
- From $134 per night (USD)
VRBO
ALMOST HEAVEN ~ 2 Bedroom, 2 Bathroom Condo with Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
UNWIND IN PARADISE… Let you worries wash away in this peaceful retreat located within the 1800 Atlantic community offeri ...
From $134 per night (USD)VRBO
- From $209 per night (USD)
VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $209 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $275 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Home away from home!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the gated community of the Key West Golf Club, enjoy your morning coffee in the enclosed back porch overlooki ...
From $179 per night (USD)VRBO
- From $495 per night (USD)
VRBO
Luxury two floor apartment in prime location of famous Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Modern & Spacious 2 story Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Sho ...
From $495 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Charming 3 bedroom blocks from Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This charming Conch Style home on Southard street is just a few blocks from Duval St and across from the old Harris Scho ...
From $600 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Key West Private Home\/Pool\/on the Water\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LOCATION LOCATION! Located on the only canal in Key West, with a protected bird sanctuary across the canal. A short Ub ...
From $299 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Old Town 4 \/4.5 house with private pool and 2 poolside cottages + outdoor shower
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Newly restored Key West property in old town. Blocks from Duval and the harbor. Private heated pool central AC washer dr ...
From $500 per night (USD)VRBO
- From $336 per night (USD)
VRBO
Beautifully Updated and Appointed; 1 block from Duval; Courtyard and Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Location, location, location. A perfect retreat to relax and recharge, or the perfect starting point to explore all tha ...
From $336 per night (USD)VRBO
- From $520 per night (USD)
VRBO
SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FAR FROM ORDINARY... Extraordinary moments and blissful surroundings lie ahead for your Key West adventure as you soak i ...
From $520 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sophisticated 2 bedroom, 1 bathroom Key West Home just steps from the white sand and salty hues of Smathers Beach, short ...
From $225 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $500 per night (USD)VRBO
- From $287 per night (USD)
VRBO
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
YOUR PIECE OF PARADISE… Residing in an attractive neighborhood at the highest point of Key West referred to as “Solares ...
From $287 per night (USD)VRBO
- From $565 per night (USD)
VRBO
PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. The downstairs living area is ...
From $565 per night (USD)VRBO
- From $622 per night (USD)
VRBO
VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Villa Serena is the perfect space ...
From $622 per night (USD)VRBO
- From $181 per night (USD)
VRBO
A “whole” in one vacation home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Amazing two bedroom townhouse with two decks, two bathrooms and a open kitchen in the famous Key West Golf Course resort ...
From $181 per night (USD)VRBO
- From $182 per night (USD)
VRBO
**LARGE PRIVATE HEATED POOL and PATIO**1\/3 Mile from Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on a quiet residential street in the beautiful key west neighborhood of casa marina just blocks from Higgs Beach ...
From $182 per night (USD)VRBO
- From $310 per night (USD)
VRBO
LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
UNMATCHED ISLAND RETREAT… Tucked away within one of the island’s most impressive lanes in the Casa Marina district, this ...
From $310 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg\/bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the Key West Shire! A sublime sanctuary where all your worldly troubles melt away and relaxation is paramoun ...
From $359 per night (USD)VRBO
- Click For Pricing
Expedia
Parrotville - 2 bedroom \/ 2 bath Townhome Close to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Parrotville is part of the Windward Park gated community just off Simonton Street, one block from Duval Street. A total ...
Click For PricingExpedia
- From $220 per night (USD)
VRBO
INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w\/ Community Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
YOUR PEACEFUL PARADISE AWAITS… Find this unmatched island escape tucked away in the lust and intimate Southernmost Caban ...
From $220 per night (USD)VRBO
- From $363 per night (USD)
VRBO
CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w\/ Pool & Compact Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
LET THE REAL WORLD SLIP AWAY... Experience quintessential island serenity within this charming and newly renovated home ...
From $363 per night (USD)VRBO
- From $1204 per night (USD)
VRBO
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w\/ Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $1204 per night (USD)VRBO