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Key West Vacation Rentals and Hotels

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Experience everything wonderful about eccentric Key West when you reserve Key West vacation home rentals from Hot Stays!

Our hotels in Key West give you a great variety of locations to choose from. Stay near the water or next to Duval Street. Request Key West bed and breakfasts near your favorite restaurant or attraction. Reserve Key West condo rentals near a specific dock to get a spectacular view of the sailboats, cruisers and fishing boats in the Key West area.

No matter where you prefer to stay or your specific vacation budget, we have an array of luxury villas in Key West for you! Traveling with family, friends or coworkers? We can comfortably accommodate a range of party sizes and find rental properties that keep everyone happy and satisfied.

Spend a full afternoon exploring everything Key West has to offer. Return to a spacious, cozy rental with all of the amenities you prefer on your upcoming Key West vacation. Let us help you search our expansive list of Key West cabin rentals now!

Find the Best Rentals in Key West for Spring Break at HotStays.com

Looking for the right Key West spring break hotels for you and your friends? Want to get a deal on Key West spring break homes and condos for your entire family? No matter if you’re going to live it up with your school mates or you’re traveling with your family, HotStays.com has the most comprehensive list of rentals in Key West for spring break fun! All of our Key West spring break hotels and Key West spring break homes and condos bring you close to the action.

Whether you want to get close to the water fun—from parasailing and scuba diving to water skiing or fishing—or you want to enjoy the serene sunsets and the mystic charm of Old Key West, HotStays.com is your first stop. Poets, philosophers and writers have soaked up the inspiration of this tropical paradise for centuries. Your spring break will be unforgettable in Key West. Browse HotStays.com for the perfect place to take in the Key West life.

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Looking for Key West hotels? View all hotels in the Key West area.

We have over 100 properties in the Key West, Florida area.
Please browse our top 30 properties below
Vacation Rentals in the Key West area.
Dream Cottage, 1 Block off Duval Street, Old Town #2744 From $198/night
1 Beds 1 Baths Sleeps 2 Cottage 10 photos
Little Palm Cottage is the perfect dream cottage... exactly what you would imagine your vacation to be. The perfect tropical oasis... Double sets of French Doors opening out to your private courtyard... high ceilings with mounted fans and a flat screen TV that can be viewed from all angles... King Size ...
Casa Manana Key West Cottage #1837 From $4,500/month
2 Beds 2 Baths Sleeps 6 Cottage 8 photos
Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining. Walking up Virginia Street brings you to White Street, the new Mecca ...
Palm Isle- Key West #500 From $168/night
1 Beds 1 Baths Sleeps 4 Apartment 5 photos
Welcome to Palm Isle – beauty and economy in Old Town Key West! Only one block west of Duval on Whitehead Street, and just doors down from the Hemingway House, this second story studio suite is equipped to make your stay in the islands comfortable and convenient. The house shares a lot with a giant ...
Luxurious Penthouse - Key West #523 From $408/night
4 Beds 4 Baths Sleeps 1-12 Condo 4 photos Real-Time Calendar
Space, privacy, luxury - what more could you ask for, this penthouse has it all. Cathedral ceiling in the living room opening to a spacious balcony overlooking the harbor/marina. Gourmet kitchen with Corian counters is equipped down to the blender for those tropical concoctions for which Key West is ...
Fully Equipped Key West Condo #518 From $178/night
1-2 Beds 1-2 Baths Sleeps 1-6 Condo 4 photos Real-Time Calendar
Our condos come with everything you could possibly need on a vacation. From the convenience of the dish washer and the washer/dryer to the relaxing heated pool you will find that your stay will be very peaceful and stress free. We have suites for two people and retreats for up to six people, so you ...
Pleasant Waterfront Condo in Key West #516 From $178/night
1-2 Beds 1-2 Baths Sleeps 1-6 Condo 4 photos Real-Time Calendar
Welcome to Pelican Landing Resort on Garrison Bight Marina. Right in the heart of Key West, our resort includes a heated pool, private balconies and much more to accommodate you during your stay. This waterfront resort with dockage is within walking distance of world class charter fishing and diving, ...
Lovely Condo on the Waterfront - Key West #515 From $178/night
1-2 Beds 1-2 Baths Sleeps 1-6 Condo 4 photos Real-Time Calendar
We offer suites (for 2 people) with one bedroom with a king bed; private bath; living room with queen sleeper sofa; dining area; fully equipped kitchen including microwave, blender, dishwasher, washer/dryer; breakfast bar seats four; living room and bedroom have sliding glass doors which open onto a ...
Bonaire Retreat - Key West #514 From $198/night
1-2 Beds 1-2 Baths Sleeps 1-6 Condo 4 photos Real-Time Calendar Pet Friendly
You will be located in Pelican Landing Resort on Garrison Bight Marina. This resort is within walking distance of world class charter fishing and diving, a short bicycle ride to the charm Old Town and right in the heart of Key West. This waterfront resort with dockage also includes a heated pool, private ...
Pelican Landing Condo in Key West #513 From $178/night
1-2 Beds 1-2 Baths Sleeps 1-6 Condo 4 photos Real-Time Calendar Pet Friendly
We offer a suite (for 2 people) featuring one bedroom with a king bed; private bath; living room with queen sleeper sofa; dining area; fully equipped kitchen including microwave, blender, dishwasher, washer/dryer; breakfast bar seats four; living room and bedroom have sliding glass doors which open onto ...
The Seaport Suite - Key West #512 From $348/night
4 Beds 2 Baths Sleeps 8 House 4 photos Real-Time Calendar Pet Friendly
Built in 1884 this large, historic building houses Re/Max Southernmost on the first floor. Seaport Suite, on the second floor, features four bedrooms and two baths – perfect for large families and groups. Furnished like the finest of captain’s quarters, this expansive suite features original Dade County ...
Toon Hall - Key West #511 From $348/night
3 Beds 2 Baths Sleeps 8 House 4 photos Real-Time Calendar Pet Friendly
Enjoy comfort, lush tropical surroundings and unmatched privacy characterizing this former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the quintessential Key West outdoor ...
Island Oasis - Key West #510 From $408/night
3 Beds 2 Baths Sleeps 6 House 4 photos Real-Time Calendar Pet Friendly
Foliage surrounds this modest Bohemian style house one block west of Duval Street. The painted Dade County Pine walls accent the antique furnishings from across the globe, including a carved headboard from Thailand and a handmade bed straight from the Costa Rican shores – topped off with local art and ...
Havana Hideaway - Key West #509 From $398/night
2 Beds 2.5 Baths Sleeps 6 Cottage 4 photos Real-Time Calendar Pet Friendly
This two story, two bedroom, two and a half bath home was built by Key West’s premier architect/contractor and has been recently renovated and landscaped. One of the newest additions to the hideaway family, Havana Hideaway is the flagship cottage, representing privacy, luxury, location and convenience. ...
Southern Cross - Key West #507 From $258/night
2 Beds 2 Baths Sleeps 6 Cottage 4 photos Real-Time Calendar Pet Friendly
Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This adorable one and a half story conch cottage, surrounded by exotic gardens, situated in the Tropical Village Compound, is the epitome of ...
The Bahama House - Key West #506 From $258/night
2 Beds 2 Baths Sleeps 6 Cottage 4 photos Real-Time Calendar Pet Friendly
This historic Bahamian-style Conch cottage is a prime example of turn-of-the-century island architecture. The modest two bedrooms, each with queen bed, two bath and queen sleeper-sofa is accented with Dade County pine walls, cathedral ceilings and island folk art, including original oil paintings, glass ...
The Orchid Suite - Key West #502 From $178/night
1 Beds 1 Baths Sleeps 6 Apartment 4 photos Real-Time Calendar
This adorable suite is bi-level decorated in a rich contemporary Danish style. The bedroom is located upstairs with a bookcase divider which separates 2 different sleeping areas each with a queen bed covered with colorful Caribbean bedspreads completes the bedroom. The upstairs bath features a tiled ...
Tropical Hideaway - Key West #501 From $198/night
1 Beds 1 Baths Sleeps 4 Apartment 4 photos Pet Friendly
Lush gardens surround this lovely restored two-story Bahamian house. This is a downstairs suite with one bedroom, full bath and features a living room with queen sleeper-sofa, cable TV, VCR, stereo with CD player, and a private telephone line with answering machine. The bedroom has a queen bed and cable ...
Harbor view penthouse - Key West #522 From $338/night
3 Beds 4 Baths Sleeps 1-10 Condo 3 photos Real-Time Calendar
A bold Penthouse that says you have arrived! With a view of the harbor from your living room and a stunning balcony seat for Key West's world class sunsets from the upstairs two bedrooms......it just keeps getting better. This centrally air-conditioned three bedroom, four bathroom, two story suite ...
Key West waterfront condo #519 From $178/night
1-2 Beds 1-2 Baths Sleeps 1-6 Condo 3 photos Real-Time Calendar
Our condos provide you with everything you could possibly need on a vacation. From the convenience of the dish washer and the washer/dryer to the relaxing heated pool you will find that your stay will be very peaceful and stress free. We have suites for two people and retreats for up to six people, ...
Tropical Village Cottage - Key West #508 From $258/night
2 Beds 2 Baths Sleeps 5 Cottage 3 photos Real-Time Calendar
The Tropical Village Cottage is the epitome of modern Key West. This two bedroom, two bath conch cottage overlooks a shared oasis-style heated pool, sun deck and poolside grilling station. With all the amenities of contemporary living set in island style and décor, Tropical Village Cottage is your ticket ...
The Tropical Retreat - Upstairs Suite in Key West #503 From $198/night
2 Beds 1 Baths Sleeps 4 Apartment 3 photos Real-Time Calendar Pet Friendly
This cute upstairs suite has two bedrooms featuring queen beds. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a tropical setting. The living room that opens onto a private veranda, features cable TV, VCR, and stereo with CD player. One bath with ...
Poolside Paradise - Key West #497 From $158/night
1 Beds 1 Baths Sleeps 2 Cottage 3 photos
Poolside Paradise is one of our most popular properties, it features all the luxuries of high end vacation rentals – from a kitchen to cable TV and VCR, private telephone line with answering machine, shaded deck and poolside location – at an affordable nightly rate. Once the winter vacation suite of ...
Well equipped waterfront Condo #520 From $178/night
1-2 Beds 1-2 Baths Sleeps 1-6 Condo 2 photos Real-Time Calendar
Our Suites (for 2 people) feature one bedroom with a king bed; private bath; living room with queen sleeper sofa; dining area; fully equipped kitchen including microwave, blender, dishwasher, washer/dryer; breakfast bar seats four; living room and bedroom have sliding glass doors which open onto a private ...
Condo in Pelican Landing Resort - Key West #517 From $178/night
1-2 Beds 1-2 Baths Sleeps 1-6 Condo 2 photos Real-Time Calendar
Come stay at our beautiful waterfront condo. Whether you want a suite for two or a retreat for up to six guests you will surely enjoy your stay at Pelican Landing. We have nearby tennis, fishing, a heated pool and much more to keep you busy during your stay. Located in the heart of Key West, we are ...
Large Penthouse condo - Key West #524 From $408/night
4 Beds 4 Baths Sleeps 1-12 Condo 1 photos Real-Time Calendar
This penthouse has it all space, privacy, and luxury . Cathedral ceiling in the living room opening to a spacious balcony overlooking the harbor/marina. Downstairs are two bedrooms with a king bed in one and two queens in the other, each with bath en-suite. Down pillows, luxury sheets, in-room safes, ...
Pelican Landing condo new Penthouse #521 From $338/night
3 Beds 3 Baths Sleeps 1-10 Condo 1 photos Real-Time Calendar
The brand new luxurious St. John Penthouse at Pelican Landing is the ideal escape for medium to large groups in Key West, Florida. This newly renovated unit is rated for six, but can easily sleep up to ten in three bedrooms with three full baths. A two story unit, both the upstairs and downstairs feature ...
Vacation Rentals in the Key West/Marathon area. (51 miles away)
Florida Keys Vacation Rentals– Atlantic Breezes #1682
2-4 Beds 2.5 Baths Sleeps 1-12 Condo 9 photos Pet Friendly
Private Waterfront setting with 50' Dock, Hot Tub, Sun Deck, Tiki Hut & Hammock- Marathon - Marathon, Florida Condo Rental 2 LARGE Luxury Waterfront condos (part of a 2 unit privately owned complex) conveniently located adjacent to each other on Sombrero Beach Road in the Florida Keys! You ...
Fantastic 2BR/2BA Marathon condo - pets welcome #1160 From $995/week, $2,700/month
2 Beds 2 Baths Sleeps 2-6 Condo 4 photos Pet Friendly
Just minutes by boat to the Atlantic or Gulf, fantastic location! We have multiple units at this complex making it convenient for large families. This 2 bedroom, 2 full bathroom, ground floor unit in Marathon comes fully furnished & equipped. King bed in the Master, 2 twin beds in the Guest, Sleeper ...
Condo in great vacation area near Coco Plum beach #1157 From $750/week, $2,100/month
1 Beds 1.5 Baths Sleeps 1-4 Condo 4 photos Pet Friendly
In a perfect location just minutes by boat to the Atlantic Ocean or Gulf! We have multiple units at this complex making it convenient for large families. This 1 bedroom, 1.5 bathrooms, ground floor unit is very clean and comes fully furnished & equipped. Screened Patio just steps from the boat ...
Marathon vacation condo close to beach #1154 From $650/week, $1,695/month
1 Beds 1 Baths Sleeps 1-2 Condo 4 photos Pet Friendly
Marathon vacation condo completely tiled and fully equipped. Queen bed and full size sofa bed in living room sleeping 3-4 comfortably. Most pets are welcome upon approval. A pet friendly and secluded beach is only a short walk away. Includes a large boat slip, DVD player, cable TV, central AC, terrace ...
We have over 100 properties in the Key West, Florida area.
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