Property List

Blue Pineapple Estate

621 Eaton Street Key West, Florida

Guests: 10
Bedrooms: 5
Bathrooms: 5

Blue Pineapple Estate, a Key West Victorian house from the turn of the 19th century, has undergone a remarkable redesign that exudes sophistication and elegance. The interior showcases a fusion of romantic architectural elements from the past and a contemporary Caribbean charm, resulting in a refined and cosmopolitan tropical style. With five bedrooms and five and a half bathrooms, this exceptional property offers a level of luxury and refinement that is truly unparalleled. Additionally, it boasts amenities such as a heated swimming pool, private parking, and is situated in a historic seaport neighborhood.

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The Calvin Klein House

712 Eaton Street, Key West, FL

Guests: 8
Bedrooms: 4
Bathrooms: 4

Famous Iconic Victorian Estate Extraordinary Designer Home Expansive Resort-Style Gardens Large Swimming Pool Wrap-around Verandahs Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic designer octagon Victorian house is often featured in notable architectural publications. Purchased and restored by superstar designer Angelo Donghia in 1976, and purchased in 1981 by famous designer Calvin Klein, it raised the bar on historic home renovation in Key West. Today it stands as a phenomenal paradise home with luxury designer decor and 5-Star amenities. Truly an amazing historic and top-of-the-line place to stay in Key West.

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Traditional Key West Estate

824 Fleming Street, Key West, FL

Guests: 22
Bedrooms: 10
Bathrooms: 7

7 BR Main House + 3 BR Guest House Heated Pool Lush Tropical Gardens Famous Historic Seaport neighborhood Stroll to Duval St. Spacious. Luxurious. Exotic. Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. A remarkable place for family and friends to stay together in a Key West weekly rental.

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Coco Plum Inn

611 Whitehead St Key West, Florida 33040

Guests: 8
Bedrooms: 14
Bathrooms: 4

The Coco Plum Inn sits in the heart of Key West's Old Town, a block from Duval Street, in between the Gulf and Atlantic coasts. We've lovingly restored the two Victorian houses that make up our inn. The first at 611 Whitehead Street was built in 1891, while the house at 615 Whitehead was constructed in 1898. Our Inn has seen its share of historic characters. The "Queen of Balido" once lived at the house at 615 Whitehead. Local legend states money from Cuban gambling was stuffed in the walls, and poker was played in our upstairs Jungle room. President Harry Truman had tea with the residents of 611 Whitehead Street during his visits to the Little White House in Key West. And then there's "Papa" Ernest Hemingway himself. He often napped on our front porch on his way home. At least that's the story. We love how wild west Whitehead Street was back in the 1800's!

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Stars and Stripes

311 Elizabeth Street, Key West, FL

Guests: 15
Bedrooms: 9
Bathrooms: 5

Abundance in Old Town Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring everyone together under one roof yet offers the perfect separation by floors for privacy too. LOUNGE Relax by the pool on a lounge chair or one of the many porches and people watch. Use one of the back porches to dine alfresco and enjoy some privacy. AMENITIES PER FLOOR First Floor: Offers one queen bedroom, a second bedroom with twins (that can be converted to a king) and both offer armoires and flat screen TVs. Between the two rooms there is a full bath with both a walk-in glass shower and claw tub. There is a queen room following these rooms adjoining with a queen suite accessible through the French doors off the kitchen or from the twin room. It offers a kitchenette and a full bath with a shower/ tub combo. Accompany these sleeping spaces is a fully stocked kitchen and spacious living room with a sleeper sofa offering an extra sleeping space for 1 - 2 guests. Second Floor: There is a queen bedroom, another room with two twin beds and a third room with a trundle bunk (twin bunk, full bottom mattress and twin trundle-sleeps 3-4). This floor shares a full bath with walk-in glass shower, a living room with dining table and a full gourmet kitchen with stainless steel appliances. Third Floor: This floor is equipped with a kitchenette, living room with flat screen and a full bath with a shower tub combo. The living room has a sleeper sofa that is best for one additional guest. The bedroom has one twin bed and a full bed meaning 1 - 3 guests could share this space. OUTDOOR LIVING AND AMENITIES There is a private, heated pool, laundry area with two of each machines, outdoor dining tables and one parking spot for the house! The Historic Seaport is in walking distance and where you will find quaint shops & restaurants. You are also just three short blocks to Duval Street and all of the attractions downtown Key West has to offer! Take a sunset cruise, go snorkeling, or grab a fishing charter. CONCIERGE SERVICES Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! OPTIMIZE YOUR TIME & SPACE IN KEY WEST!

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Key West Inn on Fleming

Key West, Florida, United States

Guests: 2
Bedrooms: 1
Bathrooms: 1

Choose from one of nine distinctly styled rooms or suites! Located in the heart of Old Town, you will find The Inn on Fleming, an historic property dating back to 1894, it offers nine quaint rooms, all fully equipped with modern amenities and fine linens. The Inn on Fleming is a private oasis in a bustling town. Whether you choose to spend time on our wraparound porch, or taking a dip in the pool, you will enjoy your time at our charming guest house. Come be a part of Key West with us, a vibrant, quaint, tropical paradise!

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