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Key West Nightly ~ Weekly Rentals

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Hermitage South

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

FALL SAVINGS! Help tourism recover with this post Hurricane Irma special: 10% off published rates until November 30th, 2017.

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...

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...

The Mermaid's Garden

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

FALL SAVINGS! Help tourism recover with this post Hurricane Irma special: 10% off published rates until November 30th, 2017.

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,...

Island Style

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

If you're looking for a stunning four-bedroom, three-bath vacation retreat with its own private pool, you've found it at Island Style. Located in Truman Annex, Key West's signature gated community, this home has it all: 2,000 square feet in a compact two-story format, porches and balconies,...

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...

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...

The Meadows House

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

FALL SAVINGS! Help tourism recover with this post Hurricane Irma special: 10% off published rates until November 30th, 2017.

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...

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...

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

FALL SAVINGS! Help tourism recover with this post Hurricane Irma special: 10% off published rates until November 30th, 2017.

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,...

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...

Banana Key

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

FALL SAVINGS! Help tourism recover with this post Hurricane Irma special: 10% off published rates until November 30th, 2017.

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...

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...

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...

La Prive

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

FALL SAVINGS! Help tourism recover with this post Hurricane Irma special: 10% off published rates until November 30th, 2017.

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...

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...

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...

Campbell Suite

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

FALL SAVINGS! Help tourism recover with this post Hurricane Irma special: 10% off published rates until November 30th, 2017.

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...

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...

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,...

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...

Bella Vita

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

FALL SAVINGS! Help tourism recover with this post Hurricane Irma special: 10% off published rates until November 30th, 2017.

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...

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...