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Pet Friendly 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...

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...

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...

La Prive

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

Reduced Minimum Night Stays for April & May!

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...

Bella Vita

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

NEW UNIT! 10% OFF already discounted prices for Open dates in April & May! Please call our office for details.

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...

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...

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...

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...

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...

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, three-bedroom, 1 full, 2 half bath home, a private residence on a block of historic architectural gems only two blocks from Duval and the Seaport. Four sea captains have made this their home and filled it...

The Sanctuary

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

10% OFF already discounted prices for April - June! Please call our office for details.

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...