Key West Florida Vacation Rentals, Hotels & Resorts


Tropical Escape at Sunrise

Key West Condo - 4.5 4.5 Star Review

Due to Covid 19, we thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR\'s: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, cable, 3 TV\'s, A/C, washer-dryer, workout center, .......read more

2 Bedroom(s)
Sleeps 5
Condo

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The Gisela, a Key West Monthly Rental

Key West Private vacation home

The Gisela is located in the rear of an adorable Conch Cottage. Finished with a soft and neutral color scheme that will take your breath away. Enter through your private entrance into the living room with features high ceilings and a spectacular light filled living space. 45-inch flat-screen TV with cable and streaming services. Between the kitch.......read more

Studio
Sleeps 1
Private vacation home

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Coral Cove #1- Queen Studio at The Galleria!

Key West Apartment - 4.5 4.5 Star Review

Summary:
Coral Cove is the perfect unit for two! It is located just steps away from the World Famous Duval Street and its shops, restaurants, bars, tours and more! There are many shared common spaces around the property to relax and enjoy as well as a shared pool!

The Space:
Coral Cove is a comfy queen studio equipped with all of your .......read more


Galleon Resort Efficiency Historic District

Key West Condo - 4.5 4.5 Star Review

$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You will not be disappointed!

Location..Location...Location...this one has it all! Resort is located on the Ocean and is within steps of famous Duval Street. The Galleon Resort offers many amenities to enhance your vacation need.......read more

Studio
Sleeps 2
Condo

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The Galleon Resort Nov 2 - Nov 9, 2019/ Boat Week 2019 Key West

Key West Condo - 5.0 5.0 Star Review

Great unit for boat week in Key West. Saturday to Saturday availability. 2 bedroom condo at The Galleon Resort sleeps 6 and overlooks the Bay with Sunset Key views, also. Watch the races from the balcony! All the amenities of an RCI Gold Crown rated resort. See The Galleon Resort website for property information. Other Galleon condo available for w.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8

Key West Private vacation home - 4.91304 4.9 Star Review

Pilar’s Secret is tucked away in the heart of Key West just half a block off famous Duval Street. This hidden oasis is the perfect spot for you to truly discover the ultimate Key West experience. Located down a quiet nondescript lane this gorgeous property is positively Key West with well appointed luxury throughout.

Pilar’s Secret offers th.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Key West Condo - 4.6 4.6 Star Review

La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic District!! Southernmost Point and Southernmost Beach on the Atlantic Ocean are just 3 short blocks away!
This is a totally renovated condo. Please check out my calendar for availability and the photos and video. <.......read more

Studio
Sleeps 4
Condo

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**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...

Key West Private vacation home

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack .......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Panoramic 3BR/3BA Condo - Direct Beach Ocean Front

key west Condo - 4.89474 4.9 Star Review

Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms, the kitchen and the living room. Birds of various types, boating activities, lush oasis gardens are just a few reasons why people keep returning to our paradise property. "Click" on \'more information\' also "click".......read more

3 Bedroom(s)
Sleeps 8
Condo

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The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6

Key West Condo - 4.89844 4.9 Star Review

This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880\'s that was converted into individual condominiums many years ago, located just one block from Duval Street in the Heart of Old Town Key West. Our casual atmosphere allows you to chill out and enjoy having the best of Key West within easy walking distance of a.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

Key West Private vacation home - 5.0 5.0 Star Review

Tranquil island living just fifteen minutes from downtown Key West. Stay in and enjoy breathtaking views of the pristine bay and coral-lined heated pool and spa with waterfall, or take a short trip and experience the remarkably unique island of Key West.
Completely remodeled two-story, five bedrooms, and four-bathroom home. You can enjoy your p.......read more

5 Bedroom(s)
Sleeps 12
Private vacation home

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CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest

Key West Cottage - 4.89041 4.9 Star Review

WELCOME TO CONCH COTTAGE!


In the 20th century many residents of Key West began referring to themselves as “Conchs”, now this term generally applied to all residents of Key West. This vacation home is called Conch Cottage because it encompasses the heart of the Key West life style.

In the heart of Old Town with traditional architec.......read more

Studio
Sleeps 2
Cottage

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Villa Paradiso: A unique mid-town paradise

Key West Private vacation home - 4.91304 4.9 Star Review

This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It features three bedrooms and three baths. The open living/kitchen area is decorated with light colored walls with striking tropical tones in the accent furnishings and tile, and soft fabrics. The dining room is outside in the attached p.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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The Maria Luz, a Key West Monthly Rental

Key West Apartment

The Maria Luz a is located in a Historic Conch house from the early 1900’s updated and decorated by its owner.
Features original hardwood floors, updated bathroom. The galley-style kitchen is fully stocked with all the necessary essentials. Other features include also features WIFI, cold A/C, private washer and dryer in the unit.
You can.......read more

Studio
Sleeps 2
Apartment

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**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…

Key West Private vacation home - 4.92105 4.9 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

Key West has a unique way of appealing to anyone and everyone that visits the island, and it\'s easy to see why: the laid-back way of life, the historic charm and walkability of Old Town, and the overall \'good vibes\' that the island ha.......read more

4 Bedroom(s)
Sleeps 10
Private vacation home

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New Listing-Key West Charmer!

Key West Private vacation home

This home was built in 1933 and was an original Key West shotgun house and has been beautifully restored. The house has been decorated uniquely and has a tranquil and beachy vibe.
Upon entry you have a front closed in office space or reading room. This room looks out to the lush landscape and is perfect for an early morning coffee or an afternoo.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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ADMIRAL'S PARADISE Gorgeous Townhome in Truman Annex

Key West Private vacation home - 4.69231 4.7 Star Review

Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with new quartz counter tops and stainless-steel appliances with a gas cook top. The large living and dining are.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Luxury Villa with Large Pool in Exclusive Area 5 min from Beach

Key West Villa

An absolute dream home in the most highly sought after location of Key West - the Casa Marina. You will feel at home and never want to leave this thoughtfully designed home. The entire house has been meticulously, professionally redesigned. Located in the most exclusive area of Key West, steps away from the Atlantic beaches, great dining and entert.......read more

3 Bedroom(s)
Sleeps 6
Villa

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A Tropical Tradition (Gallup Arms)

Key West Private vacation home - 4.68 4.7 Star Review

Nestled in one of Key West\'s original gated "mini-compounds," the Tropical Tradition vacation rental is a spacious 1990\'s three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40\' X 16\' swimming pool is the main focus of this unique .......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…

Key West Private vacation home - 5.0 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

Spanning an exclusive corner lot in the desirable Mid Town neighborhood of Key West is a stunning compound-style home designed as the ultimate vacation destination for a family or group of friends seeking privacy and quiet only a short b.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Ocean16 -spacious and relaxing Villa in Key West 15 min from Duval

Key West Villa - 5.0 5.0 Star Review

Bring the whole family to this great place with lots of room for fun...enjoy the heated pool, spacious backyard, kayaks and paddleboards, ping-pong table, outside kitchen, little beach, tiki hut bar and open water views........read more

6 Bedroom(s)
Sleeps 17
Villa

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**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR/2BA Condo & Pool + LAST KEY SERVICE

Key West Condo - 5.0 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

OLD TOWN OASIS is back! After three years out of the rental program, this luxurious condo has returned, with all the same elegance enjoyed by many guests since 2004, and with many improvements.

You’ll be staying right near the oce.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Cayo Cruz Suite - Colorful Condo with Sunset View!

Key West Condo - 4.6 4.6 Star Review

Summary:
Paradise awaits you in this renovated, 2 bedroom/2 bathroom condo in the highly desirable community of Sunrise Suites! The colorful decor and Salt Pond views are just a few highlights of this island retreat. Walk down to the shared heated pool and hot tub equipped with lounge chairs for relaxing, or take in the salt air on one of the ma.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Rare Penthouse 2 bed/2bath additional King in loft

Key West Condo - 4.6129 4.6 Star Review

Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath jacuzzi, have front row seats to the variegated lights of Mother Nature\'s Sunrises, have the convenience of a fully equipped kitchen, two sitting areas for extra comfort and flexibility and for countless hours to enjoy the view.......read more

2 Bedroom(s)
Sleeps 8
Condo

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RARE 3BR Galleon Suite Marina+Beach+Sauna+Pools+Gym+BBQ in Old Town Key West!!

Key West Hotel resort

Thank you for Visiting Chimera Vacations LLC.!

Please verify availability prior to booking.

7-Night Stay for Special Rates (Sat-Sat, Sun-Sun Check-In/Check-Out) - otherwise additional fee may apply. Inquire for exclusive rates or Feel free to request a custom rate for your specified dates of travel.

We look forward to welcom.......read more

3 Bedroom(s)
Sleeps 8
Hotel resort

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Lifetime memories/Private pool/WiFi/Dog OK/Self check-in-out/High Cleanliness!

Key West Private vacation home - 4.88889 4.9 Star Review

This elegant home has been constructed to the highest standards and is located within minutes of downtown Key West (via automobile or bike path) Yet very private and away from the tourist. Private heated pool. Decorated with exquisite comfortable furnishings incredible paintings and sculptures from renowned artists. This is one of the most impr.......read more

4 Bedroom(s)
Sleeps
Private vacation home

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Cozy studio cottage in Old Town Key West

Key West Cottage

Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to restaurants, docks, and Duvall St. Easy to get to everything yet quiet and secluded........read more

Studio
Sleeps 4
Cottage

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~ROOSTER CONCH~ Tropical Suite in PERFECT Location w/ Shared Pool

Key West Apartment - 4.88235 4.9 Star Review

THE PROPERTY: Welcome to Rooster Conch, a Key West hidden gem located in the heart of Old Town. The vacation rental is located in perhaps the best location you could ask for — just 2 short blocks from Duval Street. You are within walking distance to anything and everything you will want to experience during your tropical Florida Keys vacation.
<.......read more

Studio
Apartment

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Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

Key West Private vacation home - 4.8587 4.9 Star Review

Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only 1/2 block from the fabulous shops, restaurants and bars that made Duval Street famous.

Beautifully furnished and luxuriously appointed, Bahama House has three bedrooms, all with private.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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July 23 , 2022 > July 30, 2022 The Banyan Resort - Saturday to Saturday

Key West Hotel - 5.0 5.0 Star Review


This green / sustainable resort is close to Key West Film Society, Mallory Square, and Duval Street. One bedroom vacation unit with lavish balcony with a view of the tropical gardens, two pools, spa tub, and courtyard. Separate sitting and dining areas. One queen bed and one sleeper sofa bed. iPod docking station, 32 inch television with cab.......read more

Studio
Sleeps
Hotel

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Find many Hotel Options and hundreds of Beachfront Vacation Rentals in Key West.

Spend quality time with your family and friends at cheap low rates you can afford, all while near the beach, nightlife, entertainment and a wide variety of beach activities. We have historic Key West Vacation Rentals, you may even find a Vacation Rental with Boat Dock or Boat Slip. Hundreds of properties to choose from, search for availability, photos, descriptions and best price. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest.

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