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Your Key West Vacation Rental Experts
Founded with a commitment to preserving Key West's artistic and cultural identity, Vacation Homes of Key West offers curated vacation rental experiences that blend historic charm with modern comfort. Our properties span diverse neighborhoods, from the literary-inspired White Street Gallery District to beachfront condos and family compounds, each meticulously maintained to reflect the island's creative spirit. With decades of local expertise, we prioritize direct bookings to eliminate third-party fees, ensuring guests receive the lowest guaranteed rates and personalized service from reservation through check-out.Our team's deep knowledge of Key West's neighborhoods, cultural events, and hidden gems empowers guests to experience the destination authentically. We maintain rigorous quality standards across our portfolio, with regular property inspections and guest feedback integration to continuously enhance stays. As stewards of Key West's heritage, we collaborate with local artists and businesses to support the community while delivering exceptional hospitality experiences that celebrate the island's unique character.
Services
Vacation Rentals
Concierge Services
Travel Insurance
Monthly Rentals
Neighborhood Guides
Highlights and features
- We guarantee the lowest rates with direct bookings, saving 10%+ versus third-party platforms
- Our local team provides personalized recommendations for authentic Key West experiences
- Properties undergo regular quality inspections to ensure exceptional cleanliness and maintenance
- We offer 24/7 guest support for check-in assistance and emergency needs
- Our portfolio includes exclusive access to historic and artistic neighborhood properties
What people say
Immaculate condition
Best rental company
Amazing communication
Super clean
Stellar property
Services
Vacation Rentals
We offer curated vacation homes across Key West's most desirable neighborhoods. Our portfolio includes historic conch houses, beachfront properties, and luxury compounds. Each rental undergoes rigorous quality checks to ensure exceptional cleanliness, modern amenities, and authentic island charm for memorable stays.
Concierge Services
Our local experts provide personalized recommendations for dining, cultural events, and hidden gems. We assist with reservations, transportation arrangements, and special requests to enhance your Key West experience from arrival through departure.
Travel Insurance
We offer comprehensive travel insurance options to protect your investment. Coverage includes trip cancellations, medical emergencies, and unexpected disruptions, providing peace of mind for your vacation planning.
Monthly Rentals
Our seasonal rentals cater to extended stays with fully equipped homes. Enjoy discounted rates for month-long bookings while experiencing Key West's unique neighborhoods like a local resident.
Neighborhood Guides
We provide curated guides highlighting each area's cultural landmarks, dining spots, and recreational opportunities. Our resources help guests explore Key West authentically, from historic art districts to beachside communities.
Questions
What types of vacation rentals do you offer in Key West?
We provide diverse options including historic conch houses, beachfront condos, luxury compounds, and boutique properties across Key West's neighborhoods, accommodating groups from 2 to 21 guests.
Why should I book directly with Vacation Homes of Key West?
Direct bookings eliminate third-party fees, guaranteeing the lowest rates. Our local team offers personalized service, 24/7 support, and insider knowledge to enhance your stay.
How do check-in and check-out processes work?
We provide detailed instructions with key pickup locations and digital check-in options. Our team ensures smooth arrivals and departures with flexible arrangements based on property availability.
Are your properties pet-friendly?
Some rentals allow pets with prior approval. We'll help identify suitable options and communicate specific requirements to ensure comfortable stays for guests and pets.
What amenities are included in your vacation homes?
Properties feature full kitchens, linens, Wi-Fi, and outdoor spaces. Luxury rentals include pools, premium appliances, and unique amenities like rooftop terraces or beachfront access.
How do you maintain property quality standards?
We conduct regular inspections and maintenance checks. Guest feedback drives continuous improvements, ensuring all rentals meet our rigorous cleanliness, safety, and comfort requirements.
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Reviews (5)
Marguerite Moore
Jun 21, 2022
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The Caroline Estates House was Absolutely Beautiful and was Perfect for Our Family and Friends Party of 10. The Pool Cottage was adorable and worked out Great for Us. The pool area was very Tropical and Wonderful for when we all just wanted to stay home and laze around the pool. Location was Fabulous as we were very close to Duval Street and all the activities we did, ie Ghost Tour, Snorkeling, Sunset Sail.
I have been coming to Key West for many years and this was the first time I rented a house and we will definitely be renting through VHKW again. It was very easy to work with them and the check in and check out process was so easy. Fabulous Vacation!
I have been coming to Key West for many years and this was the first time I rented a house and we will definitely be renting through VHKW again. It was very easy to work with them and the check in and check out process was so easy. Fabulous Vacation!
Mitch Dingus
Jun 17, 2022
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Great location right on the Atlantic ocean. Beautiful view. Close to everything on both ends of the island. Located in a very quiet gated complex. Nice, well kept pool and grounds. Hotel luggage carts made it nice as did shopping carts for bringing up groceries. Would stay here again.
Amy McIntire
May 29, 2022
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What a spectacular getaway in Key West! This house was more than we hoped for. Location is everything in key west and this house provided the perfect walking distance to Duval, it was refreshing to come home to the house and jump in the pool after a hot day/night on Duval. This house accommodated our large group of 10 easily. It came fully equipped with anything you'd need including spices in the kitchen. CVS was close enough we bought a couple extra floats. Will be booking again next year! Thank you VHKW for sharing such an incredible home!
Ted Mahoney
Jan 09, 2022
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The entire experience was great. From the time I made an inquiry about renting through the contract process was very easy. Anytime I had a question, someone at the office was helpful in getting the correct answer. The Tropical Tranquility property was perfect for my family. Each family member had their own space and the common areas were large and open enough for all of us. The location was ideal to get around Key West especially with a golf cart. If I return to Key West, I will check on this property first.
Con Jay
Dec 04, 2021
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Love those iguana visitors we had! Twin cottages were cute, clean and convenient to everything. Staff are superb as well.
