Fleming Key Rentals
- From $359 per night (USD)
VRBO
New Conch cottage, with heated pool, walking distance to downtown Key West.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cathedral ceilings, Viking and Wolf appliances, quartz counters, wood floors, private heated pool, BBQ, waterfall and ...
From $359 per night (USD)VRBO
- From $383 per night (USD)
Expedia
Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 story Townhouse is in "Old Town Villas". A Caribbean inspired community in the heart of Key West. Built in 2017. ...
From $383 per night (USD)Expedia
- From $481 per night (USD)
VRBO
**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $481 per night (USD)VRBO
- From $157 per night (USD)
VRBO
ESCAPE ON FLEMING - A charming 2 bedroom home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL ... This property is not allowed to accept pets. Break away from it all at Escape on Fleming. Thi ...
From $157 per night (USD)VRBO
- From $246 per night (USD)
VRBO
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Pool & Dog-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Introducing 'The Conch Chateau' – a stunning and recently updated Conch House nestled in the heart of Key West's charmin ...
From $246 per night (USD)VRBO
- From $425 per night (USD)
Expedia
The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your tropical vacation, whether work-free or not, in this Old Town home only a couple of minutes from Duval and Wh ...
From $425 per night (USD)Expedia
- From $212 per night (USD)
VRBO
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Keys Please Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $212 per night (USD)VRBO
- From $389 per night (USD)
Expedia
Single home with pool, center of Old Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful, newly renovated single home of corner lot in the center of old town. 4 blocks from Duval and 4 blocks from se ...
From $389 per night (USD)Expedia
- From $529 per night (USD)
VRBO
Large waterfront 2\/2 end unit with boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $529 per night (USD)VRBO
- From $488 per night (USD)
Expedia
Best Location - Luxury 4 BR Home w\/pool in Key West - Steps to Duval & Seaport
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
This pre-1900's historical property just underwent a multi-million dollar renovation. No expense has been spared to brin ...
From $488 per night (USD)Expedia
- From $312 per night (USD)
VRBO
Old Town Classic with plenty of charm, porch swing and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful home with covered porch and swing! Full kitchen, washer/dryer, TV, Internet, A/C, separate patio area with twi ...
From $312 per night (USD)VRBO
- From $336 per night (USD)
Expedia
\"A Bird's Eye View\" at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stunning, Modern 2 bedroom, 1 bathroom second floor condo in the Truman Annex Shipyard Complex completely renovated. Ful ...
From $336 per night (USD)Expedia
- Click For Pricing
Expedia
Rose Haven in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
If you want to engage with Key West's past and be perfectly positioned to take advantage of its present, Rose Haven is t ...
Click For PricingExpedia
- From $1392 per night (USD)
VRBO
Downtown 4\/4 Waterfront Penthouse Pool, Dock, Pet
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Bring your family & friends to this 2400sqft waterfront Penthouse condo. Boat slips available on site with com ...
From $1392 per night (USD)VRBO
- From $1260 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Dock, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Bring your family & friends to this 2000sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1260 per night (USD)VRBO
- Click For Pricing
Expedia
Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
BOOK NOW! Walk down the secluded brick path of the 4-unit compound, past the tropical foliage to Unit B, adjacent to the ...
Click For PricingExpedia
- From $490 per night (USD)
VRBO
**MARGARET’S MAGIC COMPOUND @ SOLARIS HILL** Old Town Compound & Pool + LAST KEY
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Travelers fro ...
From $490 per night (USD)VRBO
- From $615 per night (USD)
Expedia
Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy all of Key West's exciting activities from the privacy and comfort of your own two-story, historic home in Old Tow ...
From $615 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Campbell Eyebrow House
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
The uniqueness of Campbell Eyebrow House starts with its Classical Revival "eyebrow" styling, an iconic gable roof creat ...
From $225 per night (USD)VRBO
- Click For Pricing
Expedia
Truman House in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home w ...
Click For PricingExpedia
- From $112 per night (USD)
VRBO
Campbell Cottage in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location...Location...Location! Campbell Cottage is perfectly located to walk to almost everything Key West has to offer ...
From $112 per night (USD)VRBO
- From $325 per night (USD)
Expedia
The Courtyard in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spring Special - Price Discounted!Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyar ...
From $325 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Paradise Grand in Key West
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Experience paradise in sumptuous style. That's what Paradise Grand, a breath-taking yet comfortable five-bedroom, four-b ...
From $400 per night (USD)VRBO
- From $151 per night (USD)
Expedia
Anchor's Away in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom ...
From $151 per night (USD)Expedia
- From $346 per night (USD)
VRBO
Ann Street Gardens in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key ...
From $346 per night (USD)VRBO
- From $280 per night (USD)
Expedia
Coral Condo in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom ...
From $280 per night (USD)Expedia
- From $160 per night (USD)
VRBO
La Hacienda in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most dis ...
From $160 per night (USD)VRBO
- From $355 per night (USD)
Expedia
Campbell Suite in Key West
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell S ...
From $355 per night (USD)Expedia
- From $94 per night (USD)
VRBO
Bay's Hideaway in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just the mere idea of planning a vacation puts a smile on most faces. If your vacation includes a stay in the Conch Repu ...
From $94 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Quilted Giraffe in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes yo ...
From $550 per night (USD)Expedia
- From $200 per night (USD)
VRBO
MONTHLY - 1 block from the Seaport and 2 blocks from Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautifully decorated property has soaring ceilings with a lovely outdoor dining & bbq area and is walking distance ...
From $200 per night (USD)VRBO
- Click For Pricing
Expedia
Rose Treehouse in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in i ...
Click For PricingExpedia
- From $133 per night (USD)
VRBO
Conch Republic Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
SPRING Specials! Rates Discounted.This historic conch home, circa 1890, is your dream vacation spot. The welcoming prope ...
From $133 per night (USD)VRBO
- From $1100 per night (USD)
Expedia
Four Condos w\/ Entertainment, Private Parking & Beach Nearby - Great for Groups
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Three Flowers Guesthouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $1100 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Paradise on Windsor-3 bedroom 4bath Old Town home w\/private pool, guest suite
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $250 per night (USD)VRBO
- From $880 per night (USD)
Expedia
Kemp House in Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of ...
From $880 per night (USD)Expedia
- From $1334 per night (USD)
VRBO
Bayview Manor at Paradise Harbor with Private Pool and Dock!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1334 per night (USD)VRBO
- From $191 per night (USD)
Expedia
Bohemian island home full of color and modern amenities - in a great location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Del Sol Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $191 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Experience Key West’s “Tropical Luxury.” Paradise Found!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your private Key West getaway located in Old Town. This stunning home offers the perfect blend of comfort, s ...
From $400 per night (USD)VRBO
- Click For Pricing
Expedia
5 Star Timeshare Resort - The Galleon located in Old Key West, Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon, in the heart of "Old Town Key West" located on the historic Seaport/Marina and a short walk to world famous ...
Click For PricingExpedia
- From $353 per night (USD)
VRBO
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn ...
From $353 per night (USD)VRBO
- Click For Pricing
Expedia
Beautifully decorated home located in the White Street Gallery District.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
On The Rocks is a beautifully renovated and decorated home located in the White Street Gallery District. It combines the ...
Click For PricingExpedia
- From $825 per night (USD)
VRBO
Angela's Conch Cottage - Old Town\n\"Extraordinary Home & heated Pool\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Angela’s Conch Cottage, as seen on HG TV's House Hunters, is located in the heart of Old Town Key West, across from the ...
From $825 per night (USD)VRBO
- From $463 per night (USD)
VRBO
Perfectly Located to Everything! Bicycle Rental, Onsite Dining, 3 Pools!
- 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 $463 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Peaceful and relaxing setting with the feel of the island!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
$6,000 per month If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and ...
From $250 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Beautiful Two-Bed, Two-Bath Suite at Galleon Resort Overlooking Harbor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Our space is a lovely two-bedroom, two-bathroom serviced apartment with harbor views located on the second floor of The ...
From $400 per night (USD)Expedia
- From $553 per night (USD)
VRBO
**TRUMAN’S TROVE @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hunting for t ...
From $553 per night (USD)VRBO
- From $895 per night (USD)
VRBO
SEAPORT SAILING at Galleon Resort—Southernmost Regatta-Marina-Beach-Pool-BBQ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OCEANFRONT CASUAL LUXURY MARINA PENTHOUSE CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO ...
From $895 per night (USD)VRBO
- From $327 per night (USD)
VRBO
Dog-friendly downtown home & casita with patio, W\/D, & central\/partial AC
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Sunshine Stunner & Casita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $327 per night (USD)VRBO
- From $121 per night (USD)
Expedia
The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared Pool & Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Introducing 'The Oasis' – a beautifully updated 1BR home ideally situated near the intersection of Old Town and the Whit ...
From $121 per night (USD)Expedia
- From $130 per night (USD)
VRBO
Blue Heron by AvantStay | Pool & BBQ in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*This condo is available for 28+ day stays only, and the pool area is shared with 3 other condos.* Welcome to our charm ...
From $130 per night (USD)VRBO
- From $269 per night (USD)
Expedia
Open and spacious home near Key West activities with WiFi, AC, & private W\/D
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Key West Holidays Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $269 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Ashe St Serenade: 3BD\/3.5BA Luxury Retreat, Private Pool in an Island Oasis.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excite ...
From $340 per night (USD)VRBO
- From $128 per night (USD)
Expedia
Dog-friendly downtown studio near beach with WiFi, AC, fridge, oven, microwave
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sunshine Casita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $128 per night (USD)Expedia
- From $225 per night (USD)
VRBO
**PERFECT HARMONY @ MIDTOWN** 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! PERFECT HARMO ...
From $225 per night (USD)VRBO
- From $226 per night (USD)
Expedia
Lavender on White - 3 BD \/2 BA House w\/ Private Heated Pool and great Kitchen
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in a prime location, Lavender on White offers the perfect blend of tranquility and accessibility. Situated in th ...
From $226 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Priced to Book! 1BR\/1BA Walking distance to Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
From $200 per night (USD)VRBO
- Click For Pricing
Expedia
Key West “Blue Zone” Oasis with Pool, Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Unwind and reconnect with nature at our tranquil VRBO property. As you enter the serene sanctuary, you'll be enveloped b ...
Click For PricingExpedia
- From $550 per night (USD)
VRBO
The Crystalmarine Suite – Rustic Luxury on the Sea
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Romantic getaway on the sea with panoramic views of the ocean. Capture each sunrise and sunset on board this one-of-a-ki ...
From $550 per night (USD)VRBO
- From $217 per night (USD)
Expedia
The Saltbox in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New Unit! SPRING Specials! Rates Discounted.Historically, The Saltbox is an architectural form as well as a traditional ...
From $217 per night (USD)Expedia
- From $536 per night (USD)
VRBO
LUXURY Retreat in Old Town, Key West!
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 4
Historic 1880's home awarded by the Historic Florida Keys Foundation in a prime old town location. A mere 5 blocks from ...
From $536 per night (USD)VRBO
- Click For Pricing
Expedia
Adorable Cottage Retreat in the Heart of Old Town - Steps from Duval - Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the heart of Old Town Key West and experience the perfect blend of historic charm and modern comfort. This bea ...
Click For PricingExpedia
- Click For Pricing
Expedia
Waterfront resort where you can enjoy restaurants &more within walking distance
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the heart of Old Town Key West, The Galleon Resort & Marina has been the vacation choice of many families and ...
Click For PricingExpedia
- Click For Pricing
Expedia
Amazing Location 3bed\/2bath & Swim Spa\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Fully furnished ground floor cottage with 3 bedrooms (queen bed in each), 2 full bathrooms, plus a loft with an addition ...
Click For PricingExpedia
- From $5812 per night (USD)
VRBO
Combined Bayview Manor and Bayview Retreat, accommodating up to 22 guests!
- Bedrooms:
- 7
- Bathrooms:
- 9
- Sleeps:
- 22
Enjoy the comfort of accommodating up to 22 guests, in beds, over two luxury waterfront homes on Garrison Bight! Central ...
From $5812 per night (USD)VRBO
- From $550 per night (USD)
Expedia
NEW MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Charming Key West Oasis - Perfect Blend of Tranquility and Vibrancy! Escape to a hidden gem nestled on a serene lane be ...
From $550 per night (USD)Expedia
- From $1100 per night (USD)
VRBO
Hyatt Vacation Club at Sunset Harbor\n2 Bedroom
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical Key West welcomes you to a classic Florida villa offering a primary room with a plush king bed and connecting b ...
From $1100 per night (USD)VRBO
- From $1373 per night (USD)
Expedia
Knowles House
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 12
Short walk to famous Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Convenience of ...
From $1373 per night (USD)Expedia
- From $650 per night (USD)
Expedia
Beautiful Ocean View 2 Bedroom Condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Prime location and views of the ocean? This condo has both! It’s situated right off the beautiful marina and located a f ...
From $650 per night (USD)Expedia
- From $2000 per night (USD)
Expedia
1983 65 foot Hatteras Motor Yacht
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
You and your friends and family will Spend your days like royalty aboard a fully refurbished Hatteras Motor Yacht. Exper ...
From $2000 per night (USD)Expedia
- From $935 per night (USD)
VRBO
Coco's Hideaway in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coco's Hideaway is a 3 level townhome that is part of a mini-compound complete with lush tropical gardens and a huge sh ...
From $935 per night (USD)VRBO
- From $501 per night (USD)
VRBO
Amanda`s Garden Getaway 3 BR \/ 2 BA with shared large pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Amanda's Garden Getaway is one part of a mini-compound that offers the privacy of a gated property with a large shared p ...
From $501 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Tree House Retreat - 2 Bedroom \/ 1 Bath with large shared pool
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Tree House Retreat is located on the second floor of Amanda's Garden Getaway. It offers a large living room with frenc ...
From $405 per night (USD)VRBO
- From $986 per night (USD)
Expedia
Truman House in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home w ...
From $986 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Downtown Sunset Harbor Studio!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a great studio unit at Hyatt Sunset Harbor in downtown Key West. Walk along the boardwalk or head to Duval Stree ...
From $300 per night (USD)VRBO
- From $189 per night (USD)
Expedia
Casa Tranquila-2 bedroom 2 bath Old Town home w\/ jacuzzi, outdoor grill
- Bedrooms:
- 2
- 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 $189 per night (USD)Expedia
- From $160 per night (USD)
VRBO
Lazy Lane Cottage in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NEW UNIT! SPRING Specials! Rates Discounted.A picturesque lane plus a charming 2 bedroom, 2 full bath conch cottage set ...
From $160 per night (USD)VRBO
- From $1100 per night (USD)
Expedia
OLD TOWN LUXURY HOME - completely remodeled, updated, steps to Duval Street.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the heart of Old Town, this rare home has 3 Bedrooms with 3.5 Baths in the Main House. New in 2021 to the hig ...
From $1100 per night (USD)Expedia
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VRBO
Coastal Key Cottage | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful 2 bedroom, 1 bath home offers you the quintessential Key West experience, just steps away from all the is ...
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- From $222 per night (USD)
Expedia
Windsor Cottage | Quaint Old Town Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Perfectly located in the heart of Old Town, this contemporary cottage offers an ideal and central location. New ...
From $222 per night (USD)Expedia
- From $165 per night (USD)
VRBO
NEW! Treasure Trove | One-of-a-Kind Key West Loft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Dating back to 1919, Casa Antigua has a rich history as a one-of-a-kind property in downtown Key West. As one o ...
From $165 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Snowbird-friendly oasis with private heated pool, lush yard, & ample parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Orchid House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $351 per night (USD)Expedia
- From $339 per night (USD)
VRBO
**SPIRIT OF KEY WEST @ OLD TOWN** Exquisite Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SPIRIT OF KEY ...
From $339 per night (USD)VRBO
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VRBO
Key West Retreat: Private Balcony, Fitness Center, Tiki Bar
- Bedrooms:
- 4
- Bathrooms:
- 8
- 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
- From $634 per night (USD)
VRBO
1-Bedroom Suite at a 4⭐️ Hotel
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 King Bed600-sq-foot (56-sq-meter) room, balcony with ocean viewsLayout - Bedroom Internet - Free WiFi Entertainment - ...
From $634 per night (USD)VRBO
- Click For Pricing
VRBO
Key West Coastal Escape: Modern Unit, Daily Housekeeping, Tiki Bar
- 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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
Duval Street Retreat: Modern Unit, Daily Housekeeping, On-Site Dining
- Bedrooms:
- 3
- Bathrooms:
- 6
- 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
Seaside Sanctuary: Modern Design, Bicycle Rentals, 3 Pools
- Bedrooms:
- 3
- Bathrooms:
- 6
- 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 $206 per night (USD)
VRBO
The Bird of Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the pinnacle of refined island living at The Bird of Paradise, gracefully positioned along the estee ...
From $206 per night (USD)VRBO
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Expedia
Dog-friendly condo near beach with pool, grill, outdoor shower, W\/D, AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise on Packer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $361 per night (USD)
VRBO
The Perch on Duval- Hip & Modern Duval Suite
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Perch on Duval, an elegant and charming 2-bedroom vacation rental situated in the heart of downtown Key West. ...
From $361 per night (USD)VRBO
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Expedia
ALL INCLUSIVE! Snorkel\/Sail\/Spear Fish\/Fishing\/Fun\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will love staying on this 45' GulfStar Sloop. The boat boasts 2 BR, 1.5 bath with shower, full working galley, A/C t ...
Click For PricingExpedia
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VRBO
Ocean Breeze Retreat: Modern 1BR Suite with Private Balcony
- Bedrooms:
- 4
- Bathrooms:
- 8
- 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
Key West Oasis: Luxury Unit on Duval St, 3 Pools, Resort Amenities
- Bedrooms:
- 4
- Bathrooms:
- 8
- 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
Vacation in Style: Spacious 1BR Condo with Poolside Tiki Bar
- Bedrooms:
- 4
- Bathrooms:
- 8
- 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
- From $634 per night (USD)
Expedia
1-Bedroom Suite at a 4⭐️ Hotel
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 King Bed600-sq-foot (56-sq-meter) room, balcony with ocean viewsLayout - Bedroom Internet - Free WiFi Entertainment - ...
From $634 per night (USD)Expedia
- Click For Pricing
VRBO
Oceanfront Haven: Daily Housekeeping, Latin Cuisine, On-Site Restaurant
- Bedrooms:
- 3
- Bathrooms:
- 6
- 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
Coastal Getaway: Daily Housekeeping, On-Site Dining, 3 Pools
- Bedrooms:
- 4
- Bathrooms:
- 8
- 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
Steps from Duval, Tropical Paradise at Hyatt Sunset Harbor Studio Apt
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perfectly situated on the wester ...
Click For PricingVRBO
- Click For Pricing
VRBO
Charming Bungalow with 3 Pools, Complimentary Breakfast & Cozy Turkish Robes
- 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' ...
Click For PricingVRBO