Key West Homes for Rent with Pool

Key West Homes for Rent with Pool

Looking for a place to stay in Key West that has its own pool? Check out these homes for rent that come complete with their own private pools! Whether you’re looking for a luxurious estate or a cozy cottage, there’s sure to be a rental that’s perfect for your next vacation.

Key West Homes for Rent with Pool

Villa Paradiso: A unique mid-town paradise

House 1615 sq. ft 3 bedrooms 4 bedsSleeps 6 3 bathrooms 3 full baths Spaces KitchenLiving RoomDeck/Patio

This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It features three bedrooms and three baths. The open living/kitchen area is decorated with light colored walls with striking tropical tones in the accent furnishings and tile, and soft fabrics. The dining room is outside in the attached pavillion with an ornate iron & glass heron detail. A unique piece of Key West. Each of the bedrooms opens to a different part of the yard, extending the private space for each bedroom outside as well. The master bedroom opens to the pool area with two walls of french doors and windows. The master bath features a large tiled walk-in shower. The second bedroom is freshly painted with cool green tones and Key West art set to inspire. The third bedroom has two twin beds that can be also be made as a king. Villa Paradiso is in a very quiet residential neighborhood in close proximity to the beaches on the south side of the island. It is an easy bike ride to Duval Street and even closer to the Casa Marina area. A retreat vacation spot. Bedding: 2 kings, 2 twin beds

4.8
4.7/5
Key West Homes for Rent with Pool

Cosmopolitan Dream- Waterfront Home w/ Boat Dock!

House 2953 sq. ft 5 bedrooms 11 bedsSleeps 16 6 bathrooms 5 full baths1 half bath

Cosmopolitan Dream is a five-bedroom, five-bath home with beautiful decor. Sleeping up to 16 guests this home features two king bed, 4 twin bed, 4 bunkbed, and a sleeper sofa

The open concept floor plan makes entertaining a breeze and encourages family time around the dining room table. A fully equipped kitchen awaits your home cooked meals or private chef experience. With high speed internet access and keyless entry vacation has never been more convenient and easy.

4.7
4.7/5
Key West Homes for Rent with Pool

~ VILLA LUXE ~Two lavish dwellings in one! King beds, pool, parking!

House 2400 sq. ft 3 bedrooms 3 bedsSleeps 7 4 bathrooms 3 full baths1 half bath

THE PROPERTY: Villa Luxe reveals a discreet but sexy glamour beyond its gates–and it’s no wonder since it was once owned by a hip clothing brand. It’s easy to imagine models and fashion industry types lounging poolside, away from the watchful eyes of others. Now, you can rent it for yourself and your fabulous friends (and everyone’s more fabulous here). This is truly a luxurious, “Adults Only” property and is not suitable for children under the age of 12.

4.9
4.7/5
Key West Homes for Rent with Pool

Old Town Key West - Historic & Charming - 2 Blks From Duval

House 1000 sq. ft 2 bedrooms 4 bedsSleeps 5 1 bathroom 1 full bath Spaces KitchenLiving RoomDeck/Patio

The health and safety of our guests and employees is our top priority. Our homes are private and ideal for maintaining social distancing (and working remotely via internet). Our private common amenities are situated on over 5,000 square feet of outdoor space – continually being refreshed by a tropical sea breeze. Access to the house is via Yale Smartlock, which can be operated by keypad or smartphone.

4.6
4.7/5
Key West Homes for Rent with Pool

**BAHAMIAN BAMBOO @ THE ANNEX** Chic Home By Duval & Beach + LAST KEY SERVICES.

House 1632 sq. ft 3 bedrooms Sleeps 6 3 bathrooms 3 full baths Spaces Balcony

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

BAHAMIAN BAMBOO has been painstakingly decorated and furnished in a sophisticated yet distinctive Bahamian style. Your lifestyle in this home will be very Bahamian as well, with large French doors that open up to provide seamless tropical indoor/outdoor living. The pool is just steps away from the living room sectional or the outdoor dining area. You’ll never want to leave this peaceful oasis, and yet you’ll be just two blocks from Duval Street. Enjoy the nightlife and it’s famous attractions, like the Green Parrot and Willie T’s to enjoy some live music, Mallory Square for entertainment and a sunset stroll. Best of all, you’ll be less than a half mile from the Fort Zachary Taylor State Park Beach for a day of snorkeling and sun. Combine the uniquely Bahamian decor of BAHAMIAN BAMBOO with the perfect location and the amenities of a private heated pool and private off-street parking, and you have the ideal spot to relax and recharge.

5.0
4.7/5