Key West Vacation Rental With Pool

Key West Vacation Rental With Pool

If you’re looking for a luxurious, yet affordable key west rental with pools included, look no further than these great vacation rentals below.

These luxurious rentals are perfect for a family or group of friends. You’ll enjoy the perfect weather and stunning scenery of Key West while relaxing in your own private oasis.

Book now and start planning your perfect getaway!

Key west vacation rental with pool

Studio 140 sq. ft Studio 1 bedSleeps 2 1 bathroom 1 full bath Spaces Deck/PatioBalcony

Andy’s Inn is the perfect little studio for two! Location is key to discovering all things “Key West” – Just 2.5 blocks from Duval Street, Andy’s Inn is just steps away from Key West’s most popular attractions. This is the perfect spot if you want to be out on the town and all you need for a cozy place to sleep!

Key west vacation rental with pool


Condo 1770 sq. ft 2 bedrooms Sleeps 5 2 bathrooms 2 full baths Spaces Balcony

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

If you dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the center of it all – PROMENADE TO PARADISE is everything you are looking for. With a spacious layout, relaxed island-style furnishings, a semi-private gated pool, and three private balconies all your own, this beautiful condo truly is the ideal place to spend a vacation in paradise.

Key west vacation rental with pool

Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool

Condo 455 sq. ft 1 bedroom 1 bedSleeps 4 1 bathroom 1 full bath Spaces KitchenLiving RoomDeck/Patio

Flamingo Hideaway

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Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access.

Key west vacation rental with pool


Townhome 1216 sq. ft 2 bedrooms Sleeps 6 3 bathrooms 2 full baths1 half bath Spaces Balcony

The sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West’s most exclusive gated community. From the Tommy Bahama furnishings and island inspired décor to the tropical outdoor courtyard, you’ll feel as if you’ve been transported to your own Caribbean island retreat. The location and accommodations of CARIBBEAN CHARM, coupled with Last Key Realty’s unrivaled Guest Services, is certain to make your island experience one you’ll treasure forever.

Key west vacation rental with pool

Classic Key West Cottage with Pool, Courtyard, Covered Front Porch

Condo 1800 sq. ft 2 bedrooms 3 bedsSleeps 6 2 bathrooms 2 full baths Spaces KitchenDeck/Patio

1 King Bed, 1 Queen Bed, 1 Sleeper Sofa – Maximum occupancy 6  (Please see Terms & Conditions for Max Occupancy rules)

FREE WiFi! – Central Air – Linens – Bath and Pool towels – Washer & Dryer – Ironing Board & iron – Full Kitchen – Refrigerator – Coffee Maker – Ice Maker – Microwave – Toaster – Cookware – Balcony – Onsite BBQ Grill – Hot Tub – Huge heated pool! – Pool bar for snacks and drinks – Onsite restaurant for light meals – Tennis – Onsite oceanfront beach – Dockage may be available for added fee – Oceanview – Nearby Medical Services – Nearby Grocery

NOTE: 3-7 night minimum stay requirement.  No arrivals on Christmas day.