Key West Florida Vacation Rentals, Key West Vacation Homes, Condos, and Cottage Rentals by Owner

Island Retreat - Key West Vacation Rentals, Florida

Located behind a private gated community you will find our comfortable, casual, private vacation home. Our home is located in Windward Park, on the corner of Simonton and Truman (US1) next to St. Mary's church in the heart of Old Town Key West. Just a block off Duval Street, you can stroll

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 4

Luxurious Oceanfront Codo - Key West Vacation Rentals, Florida

This Key West, Florida vacation rental condo is an ideal place for enjoying beach vacations with your family. Located on the ocean behind the Little White House only two blocks from Duval Street, Mallory Square and old town Key West in Harbor Place within Truman Annex, this two bedrooms and two a

No. Of Bedrooms: 2, No. Of Bathrooms: 2.5, Sleeps: 4

Beautiful 2 Bedroom Key West Condo! - Key West Vacation Rentals, Florida

Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet service. The unit is on the 3rd floor, accessible by elevator. Has completely equipped kitchen, 2 fully fur

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 6

Luxury Waterfront Key West Single Family Home - Key West Vacation Rentals, Florida

One of the most unique and desirable vacation properties on the Island of Key West. Brand New 2500 square foot Luxury Waterfront Private Single Family Home directly on the Gulf of Mexico (less than 100 Waterfront Single Family Homes exist on the island). Incredible sunset views from three upper

No. Of Bedrooms: 3, No. Of Bathrooms: 3, Sleeps: 8

Key West Old Town Private Home - Casa Manana - Key West Vacation Rentals, Florida

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 n

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 6

Maison du Soleil: Maginficent Retreat in Key West - Key West Vacation Rentals, Florida

Maison du Soleil, a Key West, Florida vacation rental is located at 617 Fleming Street, right in the heart of the Old Town. This finely detailed condo is not only the sunniest place on the block but also the classiest and also features unparalled amenities.

Our recently renov

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 4

Old Town Key West - Steps From Duval - Key West Vacation Rentals, Florida

The Freeport Suite is a bright sunny, spacious 3 Bedroom centrally located only 1 block from the shops, restaurants, galleries and excitement of Duval Street. A great space for a family or a group of friends. The Freeport sleeps up to 10 guests. Recently renovated, each bedroom has a double bed a

No. Of Bedrooms: 3, No. Of Bathrooms: 2, Sleeps: 8

Splendid Home near Ocean - Key West Vacation Rentals, Florida

Offering exotic views and all the comforts of home, Coconut Mallory Marina & Resort, our Key West, Florida timeshare rental is an ideal vacation home for two vacationers .

Key West studio timeshare rental is cozy and boasts spectacular views of the surroundi

No. Of Bedrooms: 0, No. Of Bathrooms: 1, Sleeps: 2

Relax in Key West in This Beautiful Condo by the Sea - Key West Vacation Rentals, Florida

This 2,000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a third bedroom w/bath. A pull out sofa bed allows for total accommodations for 8 people. With the master suites on opposite ends of the condo, it is a great set-up for 2 or

No. Of Bedrooms: 3, No. Of Bathrooms: 3, Sleeps: 8

Historic Inn & Cottages in Old Town Key West - Key West Vacation Rentals, Florida

There are many rooms to chose from at this tropical downtown Key West Hotel Resort. The bed and breakfast, cottages, guesthouse, mansion and inn all housed on one large property known as Simonton Court Historic Inn & Cottages. The Inn was once a cigar factory where craftsmen hand rolled some of the

No. Of Bedrooms: 25, No. Of Bathrooms: 25.5, Sleeps: 50

BAHAMA HOUSE - Key West Vacation Rentals, Florida

This historic Bahamian-style Conch cottage is a perfect example of turn-of-the-century island architecture. The modest two bedroom, 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,

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 6

The Sanctuary - Key West Vacation Rentals, Florida

The Sanctuary is located at the corner of South and Simonton Streets and consists of six studios, two street side (The Egret and Heron Studios) and four in a gated compound with lush tropical gardens (The Ibis, Osprey, Pelican, and Seagull Studios).

As you enter you will be welcomed into the ga

No. Of Bedrooms: 0, No. Of Bathrooms: 1, Sleeps: 2

Key West Waterfront Single Family Home - Key West Vacation Rentals, Florida

Incredible sunset views from three up

No. Of Bedrooms: 3, No. Of Bathrooms: 3, Sleeps: 8

Totally Private Old Town Compound - Key West Vacation Rentals, Florida

If Cleopatra and Anthony had dreamed of a Key West hideaway this spacious three bedroom, three bath “Royal Escape” would have been it! In keeping with its name and royal lineage, the Royal Escape is located in the prestigious Casa Marina district within walking distance to both beaches and Duval Str

No. Of Bedrooms: 3, No. Of Bathrooms: 3, Sleeps: 10

Kelly's Cottage - Key West Vacation Rentals, Florida

Just minutes away from Old Town Key West is Kelly's Cottage; a beautifully appointed three bedroom and three bath home away from home. Kelly's Cottage has everything you need to make your stay perfect. The cottage overlooks the community pool and clubhouse. Two huge decks allow you to enjoy the awes

No. Of Bedrooms: 3, No. Of Bathrooms: 1, Sleeps: 6

Oceanfront Condominium - 3 Bedrooms - 2.5 Baths - Free WiFi & HBO - Key West Vacation Rentals, Florida

NOTHING BETWEEN OUR BALCONY & THE OCEAN EXCEPT 20 YARDS OF SAND AND TROPICAL VEGITATION This very upscale unit is one of the largest in this tropical complex with over 2000 sq ft of living space. There is a wrap arpund deck which encompasses the entire unit. Every room has a spectacular view of

No. Of Bedrooms: 3, No. Of Bathrooms: 2.5, Sleeps: 6

Pete's Cottage With A Beautiful Natural Cypress Exterior - Key West Vacation Rentals, Florida

This property has it all! This award winning renovation offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large

No. Of Bedrooms: 4, No. Of Bathrooms: 2, Sleeps: 8

Key West Condo with Fountain - Key West Vacation Rentals, Florida

The condo is located in the Truman Annex Shipyards. Truman Annex is a gated community in center of Old Town just 2 blocks from Duval Street. You can walk to restaurants and most attractions. This is a very quiet and relaxing community.

There are 2 bedrooms with queen size beds and a pull out

No. Of Bedrooms: 2, No. Of Bathrooms: 1, Sleeps: 6

Enjoy Resort Style Vista Sol Surrounded By Lushly Garden - Key West Vacation Rentals, Florida

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees. Plan

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 4

Fantastic Casa Margarita Combined With Casual Elegance - Key West Vacation Rentals, Florida

Fantastic location combined with casual elegance makes this Key West cottage a great retreat to experience! And the historic seaport is just steps away with many restaurants, boating activities, historic sights & shops to keep you busy all day! Behind the front fence of the property you can park you

No. Of Bedrooms: 3, No. Of Bathrooms: 3, Sleeps: 6

Unique Ocean Front Beach Club #201 - Key West Vacation Rentals, Florida

Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom.

It has central heat/air, cable TV, washer/dryer, well-equipped

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 6

A tin-roof Key West cottage in Old Town in walking distance of everthing - Key West Vacation Rentals, Florida

Picture yourself in a tropical cottage in the Truman Annex with sloping tin roof, lazy overhead fans, and the beach, pool, Duval Street with its unique restaurants, charming shops, creative galleries, lively clubs and interesting tourist attractions all within a short walk. Add to that the myriad o

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 6

Houseboat Ramrod in Key West - Key West Vacation Rentals, Florida

Your best Key West vacation ever is just a phone call away! My charming Key West Vacation rental is a houseboat named Ramrod. It is permanently docked at the modern and immaculately maintained Sunset Marina - the perfect place to base any visit to the American carribean.

Away from bustle and cro

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 5

Extensive Tropically Landscaped La Brisa #405 E With Ocean View - Key West Vacation Rentals, Florida

Named for the breezes that cool you as you relax on the oceanview balcony of this 2 bedroom 2 bath condominium. La Brisa Condominiums are located in front of Smathers Beach on South Roosevelt Boulevard. Smather's Beach is Key West largest beach.

The complex has extensive tropically landscaped

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 4

Two Bedrooms Key West Condo Rental Florida - Key West Vacation Rentals, Florida

This beautiful waterfront condominium is located in Key West, Florida at the new Sunset Marina Condominium Residences. During your stay, you will enjoy all of the comforts of home. Arrange to dock your boat outside your condo & cook your own catch of the day.

Enjoy gulf breezes and spectacular

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 6