End Your Summer In Key West With A Big Splash

cloud 9 pool

End your summer in Key West with a big splash. Our collection of luxury boutique vacation rentals includes everything from intimate cottages and condos to larger, conch-style homes with indulgent outdoor rooms, pools and water features.  When you're looking for an island escape with a Caribbean beat to match the heat these exclusive abodes make the biggest impacts with their outdoor island style.  Our collection features nightly, weekly and monthly vacation rentals. And, when you've come to play and then decide to stay we can assist you with touring some of Key West's finest homes for sale, too!

Cayo Limón - Monthly Rental 2 Bedrooms 2.5 Bath Sleeps 6

Cayo Limon features all the outdoor amenities you could ask for during your Key West vacation: a private, seasonally heated pool, a covered outdoor eating area, a large gas grill, an outdoor shower and plenty of poolside seating. There is designated parking for two cars and one small dog is welcome with your visits!


Chavez House - Nightly Rental 3 Bedrooms 2 Bath Sleeps 6

Staying in this pet-friendly historic home will leave you with wonderful lasting memories of Historic Old Town Key West. Enjoy a dip in the new private pool, work on your tan on the large exterior deck!

Cloud 9 - Nightly Rental 3 Bedrooms 3 Bath Sleeps 7

When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find yourself in the private brick courtyard facing the home with its French doors and balconies. As soon as you see the beautiful custom pool with a waterfall, the clamor of Duval Street will seem miles away as you prepare to luxuriate in this completely renovated and modern home. Park your car in the off-street parking spot provided, and you’ll never need to drive it at all during your stay.

Copa Cabana - Monthly Rental 2 Bedrooms 1.5 Bath Sleeps 4

The back porch overlooks a colorful cocktail pool with whirlpool jets. The wood deck includes a patio table with an umbrella that adds to the enjoyment of the comfy wicker settee and rocker on the back porch. There is a propane grill for grilling up your catch-of-the-day!

Fair Winds at the Foundry - Weekly Rental 2 Bedrooms 2.5 Bath Sleeps 6

Private, gated community. Close to beaches and a state park, as well as Old Town’s bustling restaurants and nightlife. The condo pool is located half a block away. There is a dedicated covered parking space for one car.

Fish Camp - New Monthly Rental 3 Bedrooms 3 Bath Sleeps 8

This is the perfect place for families and fishing! You can cast your line right from the seawall. There are plenty of fish in the canal and you may even spot an occasional Manatee. Kayaks and paddle-boards are also welcome, so come enjoy the fun of vacationing on the water. After a day in the sunshine, you may rinse off in the outdoor shower or enjoy a dip in the swim spa. There is private covered parking with plenty of space for bicycles or scooters.

My Happy Place - Monthly Rental 2 Bedrooms 2 Bath Sleeps 4

To properly enjoy your afternoon and evening cocktails you need a proper cocktail pool just outside your door! It's perfect for taking a dip any time, day or night. The front porch is fabulous for people watching and waving ‘Hey!’ as a good neighbor should.

These are some very fine examples of places to end your summer in Key West with a big splash.  You'll find these and plenty more Key West vacation rentals right on our website. If you need help selecting your rental our vacation planners are happy to help you, too. Feel the heat and our Caribbean beat. Celebrate your summer in Key West with Historic Key West Vacation Rentals!