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Key West Villa Rentals
We offer Vacation Rentals: Book your Villas securely here and save!
Stay steps from the sand in a Key West Beachfront Villa designed for convenience, coastal style, and those perfect Gulf sunsets — ideal for couples, families, and anyone who wants a seamless Florida Keys getaway.
Vacation Rentals by Owner in Key West Florida.
We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for places to stay in Key West.
To book a selected property, follow the "Search Availability" button or "View Rental" for Pricing & Rates, which will take you directly on our partner website. All bookings are securely completed on our partner websites.
Amelia`s Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool
`In-the-know` travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia`s Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval, and because it is all the way at the end of an unknown lane it is well hidden from public view. Unless you`ve stayed in this villa before, there`s no-way you`d ever know it`s just steps off Upper Duval S.......
Villa 3 Bdrms/3 baths/close to everything/off st prking/Old Town/20%off Aug/Sept
READ ADDITIONAL REVIEWS -Old Town -Whitehead St- BEST LOCATION -On Whitehead St. -Steps to Duval -Any discounts offered will be taken off price shown-will send special offer that you can accept or decline…Sleeps 7 Walk to new Truman Annex water park & Ft Zach Beach or FREE community pool 7-8 blocks..OUTSIDE SHOWER.. As seen in the March 2015 issue of Island Jane Magazine, this Hemingway inspired Villa sits on the Old Samaritan Hall site where they held lots of weddings! Such a good vibe! ( Ja.......
Key West Private Pool Garden Villa - 2 Blocks from Beach
Experience true tropical Key West living as the locals do in this spacious mid-century private garden oasis home with large swimming pool and poolside entertainment cabana. Located just one block from the beach, Private Pool Garden Villa vacation rental is at once exotic and comfortable. The colorful interior walls with French doors and windows throughout the house become picture frames anchoring the lush tropical garden that surrounds the property.
Authentic tropical style is what this c.......
Poolside Queen Room Steps from Duval!
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for those travelers who do not need a suite or kitchen. With one queen-size bed, this accommodation is perfect for romantic vacations and weekend getaways for two.
* 1 Queen Bed
* Sleeps up to 2 People
* Flat Screen TV with Cable
* Shared Heated Pool
* Continental Breakfast Included
* Parking by Reservation ($15/night plus tax)
* 200 Feet from Duval Street.......
One Bedroom Deck Villa Steps from Duval!
Enjoy a wonderful Key West accommodation.
Our One Bedroom Deck Villa features a living room, a separate bedroom with king-sized bed, and a private deck. The unit also has a full kitchen with a separate dining area. It can accommodate a total of four persons: two in the private bedroom and two additional persons on a convertible sofa in the living room. Enjoy a fun filled Key West family vacation with us.
* 1 King Bed, 1 Queen Sleeper Sofa
* Sleeps up to 4 People
* Full Kitchen w.......
Poolside King Room Steps from Duval!
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-sized bed and an additional two on a convertible sofa. Our many Key West, FL vacation villas offer something for everyone!
* 1 King Bed, 1 Queen Sofa Sleeper
* Sleeps up to 4 People
* Flat Screen TV with Cable
* Shared Heated Pool
* Continental Breakfast Included
* Parking by Reservation ($15/night plus tax)
* 200 Feet From Duval Street.......
Loft Villa Steps from Duval!
Looking for where to stay in Key West, Florida? Look no further! Our One Bedroom Loft Villa features a queen bed downstairs and a cozy lofted bedroom with another queen bed, a full kitchen with dining area, and a private porch. The Loft Villa can accommodate a total of four persons: two in the front room and two additional persons in the loft reached by a ships ladder. This villa is great for a Key West family vacation.
* Two Queen Beds
* Sleeps up to 4 People
* Full Kitchen with Di.......
Oceanfront Property - 2BR/2BA - Near Smather's Beach - Poolside Bar and Grill
★Excellent Key West Location - Oceanside Resort - Two Bedroom - Two Bath - Sleeps 6
★Very Clean - Very Nice Property.
This Oceanside two-bedroom condo features a primary bedroom with a king size bed, and adjoining bathroom with a walk-in shower and a relaxing jetted tub. The guest bedroom features a queen size bed and access to full guest bathroom. There is a living room with a sleeper sofa, TV and wi-fi access. The unit can accommodate up to six people. It features a full kitchen .......
Secret Villa I @ Old Town with Private Pool, close to Duval!
- Secret Villa I -
A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own private pool. Secret Villa I is available for rent exclusively on VRBO and HomeAway. We have recently completed a total update of the Secret Villa I kitchen and bathrooms to match the beauty of her sister property, Secret Villa II. Please Note there is a Security Camera On the Front porch. Please Contact the Property Manager To Have It Disconnected if you Wish
Secret .......
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Secret Villa II -
A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own private pool. Secret Villa II is available for rent exclusively on VRBO and HomeAway. We have recently completed a total update of the pool deck to match the beauty and size of her sister property, Secret Villa I. Please Note there is a Security Camera On the Front porch. Please Contact the Property Manager To Have It Disconnected if you Wish
Secret Villa II is the .......
Two Bedroom Two Bath Balcony Villa Steps from Duval!
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, dining area, a luxurious kitchen, and two bathrooms. It can accommodate up to six people, two in each of its two bedrooms and two additional persons on a convertible sofa in the living room. Book a Key West getaway today!
* 1 King, 1 Queen, 1 Queen Sleeper Sofa
* 2 Full Bathrooms
* Sleeps up to 6 People
* Continental Breakfast Included
* Full Kitchen with Di.......
Two Bedroom Two Bath Poolside Villa Steps from Duval!
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroom Poolside Villa has two bathrooms and features Dade County pine interior walls and floors with a gracious kitchen, dining area, and living room. This spacious vacation rental can accommodate up to six people, two in each of its two bedrooms and two additional people on a convertible sofa in the living room.
* 1 King, 1 Queen, 1 Queen Sleeper Sofa
* 2 Full Bathrooms
Poolside Studio Villa Steps from Duval!
The Poolside Studio Villa is a stand-alone Key West vacation rental that features full kitchen appliances and a sitting and sleeping area for two people. The privacy of our Villas, our thoughtful amenities, and our convenient location near Duval Street makes Key West Villas a refreshing alternative to run-of-the-mill hotels. Make your getaway to Key West, Florida!
* 1 Queen Bed
* Sleeps up to 2 People
* Full Kitchen Appliances
* Shared Pool Deck
* Flat Screen TV with Cable
.......
Tropical Tranquility - 4BR Luxury Villa In Old Town Key West w Pool
Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and completely hidden from view on a sleepy artist's lane, Tropical ~ Tranquility vacation rental is a special slice of Key West you would never find on your own. While most of the colorful cottages along this cha.......
Villa Déjà vu Key West - 4BR Private Villa in Old Town Key West with Heated Pool sleeps 10
You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an instant kinship with the surroundings.
As I toured the house and the grounds of the property, I quickly realized that my brain was just catching up to my fondest memories of favorite beach .......
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
Key West Wabi Sabi is a quintessential 1930s cottage that embodies the beauty and simplicity of island-life charm. If you’re looking to be in the heart of Old Town yet want your own pool and parking space, 506 Bahama is a perfect choice for your trip. You’ll be right off Duval Street, directly across from Fausto’s Food Palace for groceries and necessities, but tucked away enough for that real vacation recharge. This thoughtfully renovated retreat preserves the home’s original character a.......
Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once historic and exotic. If you`ve ever had the opportunity to stroll the residential streets of the famous Key West Historic Seaport neighborhood, you have experienced first-hand the type of incredible architectural history embodied in this authentic turn of the 19th Century property. The location of this estate property is where you`ll find some of the most iconic.......
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select private homes to the public. A total renovation created a stunning one-of-a-kind tropical water pavilion by bridging two cottages with a pool, spacious deck and lushly landscaped garden. The pool is made bot.......
Key West Dreamin` - Private Pool Steps Off Duval
Key West Dreamin` vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one that links us to our Cuban heritage back to the late 1800`s. A stroll through this charming Upper Duval neighborhood is to rendezvous with an important part of our island`s rich cigar and rum history.
VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
29 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 large bedrooms and 4 baths for the perfect monthly getaway. The front door enters the spacious formal living room with sectional sofa sitting area with large screen tv. The room has exposed Dade County pine walls to highlight the historical part of the house. From the living room, you enter the large kitchen area with bar seating. Any chef will feel right at home here. The skyli.......
10.0 Star Review
5 Bedrooms
- Sleeps 12
Key West Vacation Rental
Pet Friendly 
Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access
Welcome to Admirals Gold, a luxurious weekly vacation rental nestled in the prestigious Truman Annex neighborhood. This 4-bedroom, 3.5-bathroom home is the perfect destination for those seeking a spacious and luxurious escape for the entire family. Quintessential Key West architecture provides an authentic lifestyle experience with a charming covered front porch, tin roof, clapboard siding, and white picket fences.
Inside, this entire 3-Story home is filled with natural light. Light wood .......
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
• Luxury 2nd & 3rd floor Penthouse
• 3 Bedrooms with private porches & 2 1/2 Baths
• 2200 square feet of living space
• Over 2000 square feet of porches and decks
• Backyard with tropical landscaping, pool & waterfall
• Huge roof top sun deck overlooking Duval Street
• off-street parking
One of a kind! Located in the heart of Old Town Key West on famous Duval St. just steps from restaurants, shops and theatres, this very unique Duval Street Luxury Residenc.......
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on Duval St.
Comprised of two buildings—a luxurious Duval St. penthouse with 3 bedrooms and 2.5 baths, and a lovely 3 bedroom, 3.5 bath guest house. The two-story penthouse is designed a.......
Modern Luxury Meets Island Privacy: Executive Villa on Exclusive Sunset Key
Experience modern island living at its most refined in this sleek two-bedroom villa on exclusive Sunset Key--a private island retreat designed for those who appreciate elegance, privacy, and comfort.
The contemporary residence blends clean architectural lines with warm coastal sophistication. The open-concept first floor features cool tile floors, a full equipped modern kitchen, and a spacious living area designed for both relaxation and connection. Natural light floods the interior, whil.......
2 Bedrooms
- Sleeps 5
Key West Vacation Rental
Gorgeous 2-bedroom villa with AC in vibrant Key West
Hyatt Vacation Club at Windward Pointe!!! Located in Key West, this villa is a dream. With two cozy bedrooms featuring a king and a queen bed, guests can enjoy restful nights. The villa includes two bathrooms, one with a relaxing jetted bathtub. A nice living room offers a sofa bed, perfect for extra guests or lounging. Comfort is key here, with heating and air conditioning to keep the temperature just right. Whether you’re unwinding after a day of exploring or spending time with loved ones, .......
2 Bedrooms
- Sleeps 6
Key West Vacation Rental