House holiday rentals in Key Haven

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Gorgeous Romantic Private Villa, Steps from Duval!

Located 20 yards from historic Duval St in the heart of Old Town Key West w/ FREE first-come, first-serve PARKING in front or $10/day. Totally remodeled, beautiful spacious & private 2 story villa sleeps 4 comfortably. New furnishings, free hi-speed wifi, 65" smart tvs, ice machine, electric fireplace in large master suite, lush garden courtyard & shared plunge pool. We provide 2 coffee/tea stations. Walking distance to everything - convenience store, CVS, bars, restaurants & entertainment.

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Funky Chicken Cottage with Shared Pool in Paradise

Funky Chicken Cottage is a charming and eclectic vacation rental located in Key West, just a short drive away from the main island on Stock Island, Florida. This 3 bedroom, 3 bathroom property is the perfect blend of comfort and style, with unique Martha DePoo art and Cuban art. The highlight of this property is the beautiful pool area, gated community. The property also features two parking spaces under the house, making it convenient for guests who are driving to the island.

Solaris Garden ~ Relax And Enjoy ~close to Duval

Solaris Garden is an artist's cottage and has some of her work displayed in this island retreat. Located on a teeny tiny quiet lane, this cozy first-floor duplex is ideal for singles or a couple. THE PROPERTY: Bohemian bits indoors and lush landscaping outdoors will give you that tropical island feeling you are looking for. Warm wood tones and exposed beams can be found in the main living area. The family room with sofa, chair, and TV is open to the kitchen and dining areas.

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Feb. Save $!$ Oceanfront 4 Bikes/2Kayaks. KING bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Gone Coastal

Relax with the whole family at this peaceful place to stay. Completely renovated 3 bedroom 2.5 bath townhome in Coral hammock. Enjoy the pool and excellent location on Stock island. Walking distance to Roostica and Hogfish grill. Dogs are welcome but not over 25lbs. Pitsbulls are not allowed by hoa.

Fleming Street 2/1 private home Key West getaway

Fleming-O (pronounced “flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and only two blocks from world famous Duval Street and its restaurants, bars, art galleries, and shops. Two bedrooom, One bath private home for your perfect Key West Vacation

Casa Capri 3 bed 3 bath sleeps 8 tropical decorate

Bring the whole family to this great place with lots of room for fun. Sleeps 8. Three bedroom house each with its own bathroom. Two king bedrooms upstairs, downstairs bedroom can have two twins or convert into a king upon request.