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Old Town Key West Rentals

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Truman House

Nightly and Weekly Rentals
4 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 10

The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly...

Kemp House

Nightly and Weekly Rentals
3 Bedrooms
3 Full - 1 Half Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only...

Valhalla

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...

Quilted Giraffe

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part...

Duval Street Suite

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment.

From your private and...

Poinciana House

Nightly and Weekly Rentals
1 Bedroom
2 Bathrooms
Comfortably Sleeps 2
Max Occupancy 4

Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging back...

Duval Square

Nightly and Weekly Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens...

The Courtyard

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs,...

Campbell Suite

Nightly and Weekly Rentals
1 Bedroom
1 Full - 1 Half Bathrooms
Comfortably Sleeps 2
Max Occupancy 2

Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell Suite, a second & third floor condo with one bedroom and 1½ baths, is the perfect place to anchor your vacation. It starts with the white...

Rose Treehouse

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole second floor with balconies off both the...

Coral Condo

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 4

Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island...

Ann Street Gardens

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 3

The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers the quintessential indoor/outdoor vacation experience you've come...

Bella Vita

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

Cozy, comfortable, affordable. Not to mention a location in the very heart of the Historic District of Upper Duval. That's why this one bedroom/one full bath rental is aptly named Bella Vita, the beautiful life. Located within La Casa de Luces building, Bella Vita features a...

Solares

Monthly and Seasonal Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

The art of island living involves making efficient use of limited space. This charming first-floor, one-bedroom apartment does just that. It occupies the rear portion of an award-winning 1890s Victorian home on Solares Hill, the highest point of land in Key West. This quiet Old Town...

Bay's Hideaway

Monthly and Seasonal Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

Just the mere idea of planning a vacation puts a smile on most faces. If your vacation includes a stay in the Conch Republic, even better. If your vacation includes this rental, Bay's Hideaway, even better still. The compact one bedroom/one bath condo provides the perfect...

La Hacienda

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most distinctive two bedroom/two bath homes. Located on fashionable Southard Street in the heart of Old Town, the first thing you notice as you arrive is...

Hilltop Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
1 Bathroom
Comfortably Sleeps 4
Max Occupancy 4

Hilltop Hideaway is near the top of Solares Hill, the highest point in Key West, a mere 15 feet above sea level. ("Hilltop" is a word the locals use loosely in Key West!) This meticulously cared for two-bedroom, one full bath condo is near the center...

La Buena Vida

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

Quintessentially Key West in terms of location and architecture, La Buena Vida won't disappoint as your next vacation rental. In fact, you'll be delighted. The location is Old Town's Bahama Village, an artsy and cultural quarter offering some of the best attractions and restaurants on the...

La Isla Vita

Monthly and Seasonal Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

Here's how to craft a perfect vacation. First, buy tickets to fabulous Key West. Second, shop for flipflops and shorts. Third, reserve La Isla Vita for your stay! This two-story, two-bedroom, three-bath home offers what you'd expect and then some. The "then-some" starts with private off-street...

Anne's Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

For luxurious vacation living, dining, sleeping, and playing, this historic Conch Home on fashionable Southard Street in the heart of Old Town hits the bullseye. It has been totally renovated, keeping its original cottage essence while adding contemporary design updates and modern functionality. The pool and...

Amelia Lane

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

DECEMBER STILL OPEN!

Sun, fun, and relaxation are the mainstays of life on the little island of Key West. To enjoy this tropical haven for yourself, the first step is securing the right accommodations. If a single-family home with three bedrooms, two full baths, a sparkling...

Serenity Now

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

This home is, or may soon be, listed for sale. Guests booking this home must agree to showing requests. We ask the listing agents/companies to limit showings to two times per week, with 24-hour notice, but cannot guarantee compliance with the number of showings. For details...

Amelia by the Sea

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

This superbly designed three-bedroom, two-bath conch house named "Amelia By the Sea" is located, as the name suggests, near sandy beaches and the wildly beautiful Atlantic Ocean. It's part of Bahama Village, a 16-block historic subsection of Old Town Key West that hosts some of the...

Anchor's Away

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom, two-full-bath conch cottage in Old Town Key West. Recently restored and updated to include amenities such as a heated pool with rainforest waterfall, granite counter tops,...