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Key West Vacation Rentals

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Admiral's Lane

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

As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old...

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...

Hermitage South

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

The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated...

The Mermaid's Garden

Nightly and Weekly Rentals
4 Bedrooms
3 Full - 2 Half Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

NEW UNIT!

Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden bursting...

The Water's Edge

Nightly and Weekly Rentals
3 Bedrooms
4 Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable...

Kemp House

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

Reduced Minimum Night Stays for March & April!

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...

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...

Banana Key

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just steps from the...

La Prive

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

Reduced Minimum Night Stays for March & April!

This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an...

Quilted Giraffe

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

This home has a unique pricing structure. While it can rent less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial Monthly Rental discounts. In addition, save 3% off published rates if you pay by check.

Your space. Your vacation...

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...

Havana Hideaway

Nightly and Weekly Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing...

The Meadows House

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

If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around...

Shipyard

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

This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give...

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...

Royal Palm

Nightly and Weekly Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

There's no better way to experience "Island Time"-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse offers privacy and...

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...

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,...

Ann Street Gardens

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

REDUCED MINIMUM NIGHT STAYS for March!

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...

Bella Vita

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

NEW UNIT!

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...

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...

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...

Conch in Training

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

The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living...

Campbell Suite

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

Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a "cozy condo hideaway in the heart of historic Key West." The historic significance is close to home. It starts with the white stucco building...

The Sanctuary

Monthly and Seasonal Rentals
5 Bedrooms
5 Bathrooms
Comfortably Sleeps 10
Max Occupancy 10

Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower. Five doors of...

Paradise Grand

Monthly and Seasonal Rentals
5 Bedrooms
4 Bathrooms
Comfortably Sleeps 10
Max Occupancy 10

Experience paradise in sumptuous style. That's what Paradise Grand, a breath-taking yet comfortable five-bedroom, four-bath estate, is all about. The house and private grounds and off-street parking occupy a whole city block of historic Old Town, exceptional spaciousness on the small island of Key West. Copious...

Island Time

Monthly and Seasonal Rentals
4 Bedrooms
2 Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

Everyone and everything in Key West goes at its own speed, a wonderfully decelerated, human-friendly pace. Locals call it "island time." It's no accident that this beautifully restored 19th century home with four bedrooms and two full baths is named "Island Time" in honor of that...

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,...

Blackbeard's Treasure

Monthly and Seasonal Rentals
3 Bedrooms
3 Full - 1 Half Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

In addition, save 3% off final negotiated rates if you pay by check.

To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant...

The Captain's Quarters

Monthly and Seasonal Rentals
3 Bedrooms
1 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

Enjoy traditional island living in this turn of the century, two-story conch home, a stand-out private residence on a block of historic architectural gems only two blocks from Duval and the Key West Seaport. Four sea captains have made this their home and filled it with...

A Dream Come True

Monthly and Seasonal Rentals
3 Bedrooms
3 Full - 1 Half Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

Without a doubt, this vacation-defining residence will become as much a part of your holiday memories as the island of Key West itself. Its two-story classic Conch architecture, centrally located in Old Town, includes two spacious master bedrooms, two full en-suite baths, one half bath, a...

Tradewinds

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

The charming character of this three-bedroom, three-bath vacation home is captured by its Tradewinds name. It invokes the sense of adventure that brought you to Key West and the romantic appeal of the island's famous tropical breezes. Celebrating outdoors and indoors and the sweet spot in...

White Street Gardens

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

Casa Angelina's covered, wrap-around veranda may be the first thing about this property that raises your heart rate above normal, but it won't be the last. Imagine yourself relaxing at the front to catch the street-side activity or cozying up on the side for privacy and...

Seaport Oasis

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

The Seaport Oasis home, built in 1898 and completely refurbished, offers you a stylish vacation indoors and out. Inside you'll find two stories with three queen bedrooms and three full baths. Outside you have a very private deck with heated dipping pool surrounded by elegant woven...

Hemingway's Library

Monthly and Seasonal Rentals
3 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and proximity...

Latitude Adjustment

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

What could be more apropos of your next vacation than Jimmy Buffet's famous lyrics "changes in latitudes, changes in attitudes, nothing remains quite the same." It's almost as if he were singing about the Key West residence aptly named "Latitude Adjustment." Featuring two bedrooms, two full...

En Plein Air

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

En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots. All the rooms have ceiling fans and air conditioners. Modern...

Anne's Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

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...

Azure Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

So you've decided to become one of those lucky enough to be vacationing in extraordinary Key West this year! Your next step is to choose just the right residence. With two plus bedrooms, two full baths, and a stellar location, Azure Hideaway could easily be your...

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...

Ananas

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

The pineapple-or ananas as it's known by its genus name-is the classic symbol of hospitality. This two bedroom, two full bath conch house, aptly named Ananas, is truly the embodiment of warm, welcoming hospitality. Its location, style, and comfort reward the lucky visitors who choose to...

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...

Conch Clubhouse

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

Six French doors dominate the architectural design of this classic two bedroom/two full bath conch style home. What better place for letting in all that ambient light and breeziness than sunny Key West, where balmy weather and crystal blue skies are the norm. If you happen...

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...

Land's End

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

Land's End is a charming one-bedroom cottage in Old Town, one block away from the Historic Seaport, a ten-minute walk to Duval Street and Mallory Square, and situated near some of the most architecturally beautiful houses on the streets of Key West. Location, location, location!

From...

Writer's Retreat

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

All you have to do is just show up. This cozy one-bedroom cottage has everything you need for your dream vacation. Inside the gated enclave, a large, heated, residents-only pool creates a visual centerpiece. It's easy to imagine yourself lazing in the shimmering turquoise water, on...

Campbell Cottage

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

Campbell Cottage is the perfect place for living large in an intimate, comfortable one bedroom/one bath cottage. A locked privacy fence surrounds the lushly landscaped Campbell Court compound, which has an enticing Monaco pool at its center. You can step off your front porch onto the...