Key West's Best Rental Company

Welcome to Key West, Florida’s southernmost city known for its vibrant culture, conch-style houses, clear waters, and Old Town neighborhood. Originally founded in 1996, Rent Key West Vacations is one of the longest standing vacation rental companies on the island of Key West. Our office is located right on Duval street, just one block from the Ernest Hemingway Museum. This position at the center of Old Town Key West allows our team to manage both short and long-term rentals for many of Key West’s most famous homes. We connect with every guest to ensure that you find the right place for your Key West Vacation.

Browse by Category

PRIVATE POOL

OCEAN VIEW

PET FRIENDLY

HISTORIC DISTRICT

NEAR BEACH

MONTHLY RENTALS - HIGH SEASON

Complete Amenities and Personal Key West Services

Our Key West condos and vacation rentals have fully equipped kitchens, linens, and laundry facilities. In addition, many properties come complete with private pools, hot tubs, and tennis courts. Our local, knowledgeable staff is available to help you discover island activities, restaurants and more. To customize your Key West vacation, please call our reservation specialists at 1-800-833-7368.

Our Featured Properties

Duval Square Retreat

2 Beds |2.5 Baths

Tropical Hideaway @ Tropical Village

2 Beds |1 Baths

Windsor Townhomes #6

3 Beds |3.5 Baths

Beach Club Paradise Penthouse #401

3 Beds |3 Baths

Tiki Beach - Big Pine Key

4 Beds |3 Baths

GUEST REVIEWS

“Key West’s Crown Jewel is a wonderful condo, with beautiful tropical decorations, comfortable beds, luxury master bath shower, fully stocked kitchen, and close, amazing views of the pool and ocean! There is a lush tropical walkway to the pool. The pool is olympic size and the focal point of the complex.”

Key West Birthday and Anniversary Family Vacation

Amazing

“This beautiful home was amazing. Everything was perfect from the furnishings, extras to the location. Excellent customer service! Will definitely rent again.”

May 2022

Kristal S., Lewisburg, PA United States

Bali Hideaway- Time well spent!

“I have been staying at Bali Hideaway for many years and will continue to do so! The place feels like my home away from home in EYW! The grounds and pool area are spectacular. And the location is the best on the island. Close to everything but quiet as can be. I am a huge fan!”

March 2022

Timothy B., Powell, OH United States

“We had 7 fabulous days on the beautiful island of Key West. Our condo was perfect for us. Excellent location, close to everything. We drove down, so I was very happy with the gated parking. The Shipyard neighborhood is beautiful, very quiet and safe.”

Liz A., Glen Allen, VA United States

Contact Us