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

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

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

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

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

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

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

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

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

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

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

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

Beautiful Private retreat In Key West Area - Key West Vacation Rentals, Florida

Our beautiful home sits on the bay side in Big Coppitt Key. Wake up in the morning to spectacularly stunning views of the Florida bay and its Mangroove made islands. The property is over 2 acres in size, providing plenty of room for an RV or any towable sized boat. The house sits at the end of a ver

No. Of Bedrooms: 6, No. Of Bathrooms: 3.5, Sleeps: 12

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

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

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

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

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

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

Idyllic Ocean View Condo in Key West - Key West Vacation Rentals, Florida

Replete with modern luxuries, this Key West, Florida vacation rental condo is part of the Hyatt Windward Pointe- a vacation club resort. Offering amazing views of the ocean, our Key West condo near beach is a perfect base to enjoy your sun and sand holiday.

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

Deluxe One Bedroom Condo in Key West Florida - Key West Vacation Rentals, Florida

Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft of air- conditioned luxury. There is a ki

No. Of Bedrooms: 1, No. Of Bathrooms: 1, Sleeps: 4

Delux Oceanfront 3 Bedroom Condo - Key West Vacation Rentals, Florida

Ocean Front 3 bedroom luxury condo. Fantastic views of the beautiful Atlantic Ocean. Sits about 10 yards from the water on Smather's beach. Fabulous pool & hot tub that views the ocean.

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

Condominiums & Apartments - Key West Vacation Rentals, Florida

Award-winning complex in the heart of Old Town Key West... There are only eighteen units in this carefully developed condo community, created for comfortable tropical living, the Key West tradition! The 20 by 40 heated swimming pool (electric heat pump) is surrounded by lush tropical foliage, and ha

No. Of Bedrooms: 2, No. Of Bathrooms: 1.5, Sleeps: 4