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Florida Vacation Rentals by Owner

Key West Vacation Rentals in the Florida Keys

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Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Key West, Florida.

We have partnered with a major provider for Vacation Rentals by Owner, directly through Florida Vacation Rental Homes. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida.


Key West House

Blue Pelican - Key West House

Blue Pelican - Comes With 6 Passenger Gas Golf Cart. Beautiful, BRAND NEW open floor plan, custom décor, private pool, gas golf cart, and ALL the amenities! KITCHEN Modern chef’s kitchen, with large island seating overlooking the beautifully appointed dining, living area, and sparkling pool. Fully stocked to the nines with chef’s quality appliances and cooking tools, as well as coordinating....

4 Bedrooms 3 Baths - Sleeps 8
Key West, FL

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Key West Guest house

Grand Bahama Suite - Key West Guest house

Grand Bahama Suite one block of Famous Duval Street. The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island Charm have been preserved while bringing you the latest in comfort and convenience. Be prepared to come to know the true meaning of Island Time! For the Grand Bahama all guests must be 25+. Just steps away from shops, restaurants....

3 Bedrooms 2 Baths - Sleeps 8
Key West, FL

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Key West Condo

Island Escape in Truman Annex - Key West Condo

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex. This lovely Island Escape Condo is a upper level condo located in the Truman Annex Shipyard a luxury gated community. Not just another rental property! Location is everything.!!! Our favorite room is the spacious covered deck that opens up from living room with ceiling fans, tropical foliage, dining/sitting for 4. The Living/Dining area has couch,....

1 Bedrooms 1 Baths - Sleeps 2
Key West, FL

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Key West House

Bahama Brilliant - Key West House

**BAHAMA BRILLIANT @ THE BEACH** Colorful Private Home & Pool + LAST KEY SERVICE. FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! A true island treasure, BAHAMA BRILLIANT captures the essence and beauty of living in the Caribbean. Located just two blocks from Higgs Beach, this modern home was built to a high standard and decorated in vibrant co....

3 Bedrooms 3 Baths - Sleeps 7
Key West, FL

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Key West Townhome

Colors of the Keys - Key West Townhome

**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE. FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking dista....

2 Bedrooms 3 Baths - Sleeps 6
Key West, FL

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Key West Condo

Smooth Sailing - Key West Condo

**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES... FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! SMOOTH SAILING has been meticulously furnished with a modern coastal feel, and the only beauty that competes with the interior is the spectacular views from your private oceanfront balcony. You'll be able to enjoy qu....

2 Bedrooms 2 Baths - Sleeps 6
Key West, FL

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Key West Condo

"JUST OFF DUVAL" ~ Heart of Key West! - Key West Condo

"JUST OFF DUVAL" ~ Charming Condo in Center of Duval St. with Parking Space!. STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items at this crisp condo centered in the heartbeat of Duval St. Located in the upbeat and lively district of Key West, this home is just steps to high end art galleries, museums, The Southernmost Point of the U.S. and all best nightl....

2 Bedrooms 1 Baths - Sleeps 4
Key West, FL

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Key West Condo

DREAM MAKER at 1800 ATLANTIC - Key West Condo

NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES. PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Let us help make your dreams come true: Enjoy your tranquil view of the deep blue Ocean and sparkling salt water pool within our tropical garden.....There is nothing like it...anywhere. You don't have to spend a fortune to enjoy a spacious, clean and comfortable Key West condo. En....

2 Bedrooms 2 Baths - Sleeps 6
Key West, FL

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Key West Apartment

Suite Blu - Key West Apartment

Suite Blu - A monthly rental apartment in a great location. Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided. This property will meet all of the demands a vacationer might have. Other amenities include a vaul....

1 Bedrooms 1 Baths - Sleeps 2
Key West, FL

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Key West Condo

Gulfside Vistas - Key West Condo

**GULFSIDE VISTAS @ THE ANNEX** Ocean Penthouse & Pool + LAST KEY SERVICE.... FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of....

2 Bedrooms 3 Baths - Sleeps 6
Key West, FL

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Key West House

La Vie En Rose - Key West House

**LA VIE EN ROSE @ BEACHSIDE** Modern Home / Large Pool + LAST KEY SERVICES.... FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! LA VIE EN ROSE is a classic mid-century modern home set in the Beachside district of Key West, just a couple blocks from Smathers Beach on Rose Street. As the lyrics to that sweet love song go, you'll be in 'a world ....

4 Bedrooms 4 Baths - Sleeps 10
Key West, FL

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Key West Condo

"VILLA AZUL" ~ Perfect Location! - Key West Condo

"VILLA AZUL" ~ Beautiful Unit Located in Truman Annex - Walk to all the Fun!. COMFORT AND VALUE IN OLD TOWN…. This second floor two bedroom condo is located in The Shipyard, a Truman Annex neighborhood.  You will enjoy being in the heart of Old Town Key West with food and fun just a short walk or bike ride away.   FURNISHINGS…. The Villa Azul offers an open floor plan with comfortable furnishings fitting of Island lif....

2 Bedrooms 2 Baths - Sleeps 4
Key West, FL

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Key West Condo

SIYC-1 - Key West Condo

Oceanfront Oasis Summ. Summary: A beautiful oceanfront suite located at the best marina in the Keys. Located off the azure waters of the Atlantic Ocean, minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel. Our prope....

1 Bedrooms 3 Baths - Sleeps 6
Key West, FL

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Key West Boat

Vacation Rental - Key West Boat

DESIGN YOUR OWN WATER ADVENTURE. A well appointed and renovated 36' Morgan Out Island Sloop, at ANCHOR with no dock, north of KW harbor . 2 guest MAXIMUM. Water and coffee complimentary. Water taxi transport is available for checking in and out between 5-7pm and 10-12 DISCOUNTED FOR MY GUESTS for insertion and extraction.For transport outside of those windows is a COST item fo....

2 Bedrooms 1 Baths - Sleeps 2
Key West, FL

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Key West Townhome

Sago Palm - Key West Townhome

Sago Palm @ the Truman Annex. The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located less than a half mile from one of the best beaches on the island. The Presidents Walk properties are two level townhouses which have private....

2 Bedrooms 2 Baths - Sleeps 4
Key West, FL

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Key West House

Banana Breeze - Key West House

Oceanview home with expansive decks and private pool in lush landscaping. "Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasis in a private waterfront retreat, with your own heated pool. Look out at the open water views while enjoying the professionally decorated interior and spacious outdoor patio. Imagine relaxing at "Banana Breeze" with friends, fam....

4 Bedrooms 3 Baths - Sleeps 8
Key West, FL

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Key West Townhome

"CORAL CABANA" ~ Tropical Comfort! - Key West Townhome

"CORAL CABANA" ~ Lush Porch Views of the Pool & Gardens, near Golf Course!. GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Coral Cabana, in the Coral Hammock Community is a gorgeous three bedroom, three bath townhome with over 2,000 square feet of indoor/outdoor living space. A tranquil pool view can be easily appreciated by relaxing on either the upper or lower balcony. FURNISHINGS... Coral Cabana was newly decorated i....

3 Bedrooms 3 Baths - Sleeps 8
Key West, FL

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Key West House

Meadows Manor - Key West House

MEADOWS MANOR - Monthly vacation rental with 3BD/2BA - Lovely covered porches. WELCOME TO MEADOWS MANOR! We are complying with the directives listed on the Monroe County website. Please be aware that information may be updated and the details of your reservation may also be required to change, potentially without much notice. If the governor issues a directive, related to Covid-19, in which we would be required to cancel ....

3 Bedrooms 2 Baths - Sleeps 6
Key West, FL

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Key West House

3/4 Time - Key West House

Oceanfront, Resort-like luxury home with private pool & lush landscaping. If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly complimen....

4 Bedrooms 4 Baths - Sleeps 8
Key West, FL

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Key West Townhome

Tailgate Key - Key West Townhome

Tailgate Key at the Key West Golf Club. Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community, | Set among lush tropical landscaping, beautiful greens and fairways of the Rees Jones designed 18-hole course. Gorgeous views of the lake and golf course from the furnished screened outdoor deck. This gated community includes a fitness center, ....

3 Bedrooms 3 Baths - Sleeps 6
Key West, FL

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Key West Condo

Riviera Americana - Key West Condo

**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES.... FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! A stay in Key West calls for a light and airy oasis, with breathtaking water views and an easy beach location to fully enjoy the ultimate of island life in America. RIVIERA AMERICANA is located in an upscale private ....

3 Bedrooms 2 Baths - Sleeps 8
Key West, FL

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Key West Condo

Awake to the Morning Reflections C437 - Key West Condo

@ Morning Reflections open April 5th onwards Great Monthly Discounts@. Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious walk in shower. King size bed with a flat screen TV ....

2 Bedrooms 2 Baths - Sleeps 4
Key West, FL

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Key West House

Dolphin Watch - Key West House

Dolphin Watch @ the Truman Annex. RECENTLY UPDATED & VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attractions and the famous Fort Zachary Taylor Beach. This home has 2 master ensuites with king beds, and there is a total of 4 bedrooms and 3 baths. The second level offers open living and kitchen area, master bedro....

4 Bedrooms 3 Baths - Sleeps 8
Key West, FL

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Key West Condo

Key West Condo - Key West Condo

Quiet, elegant, Key West Condo close to the Ocean. This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located one mile from Smathers Beach, two miles from Higgs Beach and just minutes away from the Key West Lighthouse Museum. Many species of birds inh....

2 Bedrooms 2 Baths - Sleeps 6
Key West, FL

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Key West House

Blu On White - Key West House

Blu on White · New to the Market! 4 Bed, 3 Bath-Old town w/ Pool!. NEW ON THE RENTAL MARKET This recently renovated four bedroom, three bathroom traditional shotgun house with a twist, has a master suite which can be accessed both privately and through the main house. The home has a spacious post and beam addition that opens onto an outdoor area with a heated, saltwater pool. Play bocce on the back lawn or sip G....

4 Bedrooms 3 Baths - Sleeps 10
Key West, FL

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Key West Condo

Awesome Waterfront in the Annex - Key West Condo

@ Best of the Annex Waterfront with Fantastic Weekly Rates @. A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old military Hospital building. In the mid 80's it was purchased by a developer who renovated the entire property in keeping with the existing architecture. There are six units in the main Hospital build....

2 Bedrooms 2 Baths - Sleeps 4
Key West, FL

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Key West House

Belle of the Beach - Key West House

**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…. FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! **BRAND NEW RENTAL HOME** Get the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BELLE OF THE BEACH. Fully renovated to exceed the highest level of quality ....

6 Bedrooms 7 Baths - Sleeps 16
Key West, FL

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