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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Key West, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Key West house

Viva Margarita!

**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES...

Key West is the mecca for those seeking to live life the way it is supposed to be lived: in the sunshine with a cold drink in hand. VIVA MARGARITA! was designed to house those sun-seekers. This tropically decorated three-story home has an open living ....

3 Bedroom(s) 5 Bath(s) Vacation Rental
Key West, FL

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Key West house

Brisa Fresca

**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...

A trip to Key West is like a breath of fresh air! The sounds of rustling palm trees, the scent of fragrant flowers and the smell of salt air are the rejuvenation that only the tropics can provide. This home is a breath of Key West fresh air, or BRISA ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Key West, FL

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Key West house

Vacation Home

Key West Downtown Restored Historic Home

First floor large apartment boasts all new, high end finishes, furniture and fixtures. In the quiet and exclusive Casa Marina neighborhood. Beaches, grocery store and many fine restaurants are all within just a pleasant walk. Duval is just far enou ....

3 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 6
Key West, FL

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Key West house

Meadows Manor

MEADOWS MANOR - Monthly vacation rental with 3BD/2BA - Lovely covered porches

WELCOME TO MEADOWS MANOR! Located in the sought after Meadows district, this lovely home in central to everything great Key West has to offer. This 3 bedroom, 2 bath beautifully decorated vacation home has all the comforts & style you’d expect f ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Key West, FL

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Key West house

Fun In The Sun

Fun in the Sun @ the Truman Annex

This stately 2 bedroom townhouse in the President's Walk area of Porter Lane is furnished with tropical and luxury decor, and is loaded with amenities such as TV's in each bedroom. The community is located in the Truman Annex Complex which is located ....

2 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Key West, FL

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Key West townhome

Joan's Caribbean Hideaway

Joan's Caribbean Hideaway

Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Club with two community pools and a spacious clubhouse perfect for a home away in the tropics. A quick ride will get to Downtown Key ....

2 Bedroom(s) 2 Bath(s) Townhome - Sleeps 2
Key West, FL

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Key West house

3/4 Time

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. Luxuri ....

4 Bedroom(s) 4 Bath(s) Vacation Rental
Key West, FL

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Key West house

La Grande Reunion

**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...

Traveling with a large group requires a special home. To maximize comfort, large common areas are offered both indoor and outdoor. Private bedroom accommodations with en-suite bathrooms and TVs are a must for your group. And don't forget about the lo ....

5 Bedroom(s) 6 Bath(s) Vacation Rental
Key West, FL

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Key West condo

Awake to the Morning Reflections C437

@ Reserve Morning Reflections for Monthly rent May - September 2020@

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. Rece ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West house

Starshine Key West

Starshine Key West @ the Truman Annex

Shipyard Condominiums are 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 1/4 mile from one of the best beaches on the island. The Shipyard ....

2 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 4
Key West, FL

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Key West townhome

"CORAL CABANA" ~ Tropical Comfort!

"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 ....

3 Bedroom(s) 3 Bath(s) Townhome
Key West, FL

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Key West condo

Spinnaker

Spinnaker-Waterfront Monthly Vacation Rental 2 bedroom, 2 bath-Shared Pool

Harbour Place Condominiums: View passing ships and sunsets from your own deck or balcony in the Truman Annex's most prestigious building, the former U.S. Naval Headquarters in Key West. Take in the sunshine from the lap pool overlooking the ever chan ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West condo

Shipyard 199

Paradise Found 2 Bedroom Condo with a Shared Pool Completely Renovated

Completely renovated, 7 night minimum rental. This condo has everything you want and more. Paradise is definitely found in this Non-Smoking, first floor end unit condo only two short blocks off of "happening" Duval Street in Old Town Key West. Locate ....

2 Bedroom(s) 1 Bath(s) Condo
Key West, FL

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Key West condo

Shipyard 253

Shipyard 253 - 2 Bedroom Condo with a Shared Pool

7 night minimum stay condo upstairs unit with 2 bedrooms and 1 Bathroom upstairs spacious unit with 1 queen, 2 twins and 1 pullout sofa. . The unit comes with one assigned parking spot. There is alot to see and do in historic Key West. Enjoy touring ....

2 Bedroom(s) 1 Bath(s) Condo
Key West, FL

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Key West condo

Key West Kokomo Condo Rental

Ocean Front with Ocean View. Across from Smathers beach. Sleeps 5, 2/2 baths.

"Kokomo" is what we have named our unit. It is a 2 bedroom 2 baths with queen sleeper sofa in living room . Central AC in unit, clean unit, living/dinning is open concept. Master bedroom with a king bed, with private bathroom and access to balcony. W ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 4
Key West, FL

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Key West cottage

"PINEAPPLE COTTAGE" ~ Relaxing!

"PINEAPPLE COTTAGE" ~ Adorable, Updated Cottage in Old Town with Pool!

RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. Located one block from Duval with charming porch and shared heated pool. Walk or stroll to dining, night life, galleries, shopping, and be ....

1 Bedroom(s) 1 Bath(s) Cottage
Key West, FL

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Key West condo

Vacation Home

Beautiful Duval St. Condo, Location, Location!!!!

Location, Location, Location!!! You can't find a better location than Duval St. One of only three unique units. This Condo is above and behind Antonia's Restaurant (best Italian food in Key West!). Just newly redecorated in an urban tropical styl ....

2 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Key West, FL

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Key West condo

Awesome Waterfront in the Annex

@ 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 entir ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West boat

Vacation Home

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 ....

2 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 2
Key West, FL

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Key West house

Captains Wheel

Captains Wheel @ the Truman Annex

This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home featuring an open floor plan with a great rear deck for entertaining and relaxing. The master bedroom has it's own balcony and the gue ....

2 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Key West, FL

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Key West studio

Vacation Home

Galleon Resort Efficiency in Old Town

This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view). This unit has a brand new kitchenette featuring new wood cabinets, granite countertop and new sta ....

1 Bedroom(s) 1 Bath(s) Studio - Sleeps 2
Key West, FL

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Key West house

Royal Poinciena

Royal Poinciana @ the Truman Annex

Shipyard Condominiums are 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 ¼ mile from one of the best beaches on the island. The Shipyard u ....

1 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 2
Key West, FL

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Key West condo

Island Escape in Truman Annex

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 livin ....

1 Bedroom(s) 1 Bath(s) Condo - Sleeps 2
Key West, FL

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Key West house

Latitude Adjustment

Latitude Adjustment @ the Truman Annex

This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite ....

2 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Key West, FL

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Key West condo

Anglers Retreat Crystal Waters C429

@March 2020 $7750 plus fees Anglers Retreat open @@

Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thou ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West condo

"JUST OFF DUVAL" ~ Heart of Key West!

"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 j ....

2 Bedroom(s) 1 Bath(s) Condo
Key West, FL

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Key West house

"LOST SHAKER OF SALT" ~ Relax!

"LOST SHAKER OF SALT" ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool

THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West.  Located on Southard Street just steps from Duval's many restaurants and bars.  You are in walking distance to museums, shopping, and Fort Zachary Taylor beach.  Relax on ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Key West, FL

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Key West boat

Key West Sailing Adventure

42 ft Sailboat Currently Out Of Service-Check Back With Us

Vacation Sailing Time Charter on your own private sailing vessel for a specific period of time with a customized sailing itinerary. Sunset sailing for two nights and 4 hour snorkeling 3-5 or more nights. Bird watching during migration month of Nove ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Key West, FL

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Key West house

Sun, Sea, And Sky

Sun, Sea and Sky @ the Truman Annex

Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. Sun, Sea & Sky, decorated with private art and lots of mirrored walls, boasts ....

1 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 4
Key West, FL

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Key West townhome

Eden @ The Annex

**EDEN @ THE ANNEX** Old Town Villa & Pool by Duval + LAST KEY SERVICES...

EDEN @ THE ANNEX is a charming townhome in Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, EDEN @ THE ANNEX is ....

2 Bedroom(s) 2 Bath(s) Townhome
Key West, FL

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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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