Business Details
30 Years
experience
Your Key West Vacation Rental Experts
Rent Key West Vacations has been a trusted name in vacation rental management since 1996, offering guests immersive experiences in Key West's most iconic properties. Located on Duval Street, just steps from the Ernest Hemingway Museum, our team specializes in connecting travelers with historic homes, beachfront condos, and luxury villas across the island. With over 80 curated properties, we combine decades of local expertise with personalized service to ensure every guest discovers the magic of Key West. Our staff's deep knowledge of island culture, activities, and dining ensures tailored recommendations for unforgettable stays. As proud members of the Florida Vacation Rental Managers Association, we adhere to the highest industry standards while continuously innovating to meet evolving guest expectations.From intimate one-bedroom suites to sprawling estates accommodating large groups, our portfolio reflects Key West's unique charm and diversity. We prioritize seamless booking processes, transparent communication, and ongoing support before, during, and after your stay. Our commitment to excellence has earned us enduring relationships with property owners and repeat guests who consider us their go-to resource for island getaways. Whether seeking a romantic retreat, family vacation, or event hosting space, Rent Key West Vacations delivers authentic, hassle-free experiences rooted in local expertise.
Services
Vacation Rentals
Property Management
Concierge Services
Travel Insurance
Event Planning
Details
- Year established: 1996
Highlights and features
- We offer 25+ years of specialized Key West rental expertise
- Our local staff provides personalized island activity recommendations
- We manage 80+ curated properties across Key West neighborhoods
- We guarantee transparent booking processes with no hidden fees
- We maintain industry leadership through Florida VRMA membership
Associations and certifications
- Florida Vacation Rental Managers Association
What people say
Beautiful tropical decorations
Perfect location
Excellent customer service
Home away from home
Spectacular grounds
Services
Vacation Rentals
Rent Key West Vacations offers curated vacation accommodations across Key West's most desirable locations. Our portfolio includes historic conch houses, beachfront condos, and luxury villas with amenities like private pools and tennis courts. Each property features fully equipped kitchens, premium linens, and strategic proximity to local attractions. Our reservation specialists help guests find perfect matches for their group size, budget, and preferences.
Property Management
We provide comprehensive property management services for Key West vacation homes. Our expertise includes marketing optimization, guest screening, maintenance coordination, and revenue management. Property owners benefit from our local market knowledge, established guest network, and compliance with Florida rental regulations. Our team handles day-to-day operations while maintaining transparent communication with owners.
Concierge Services
Our concierge team offers personalized assistance for guests before and during their stays. Services include restaurant reservations, activity bookings, transportation arrangements, and local attraction recommendations. We provide detailed property guides with neighborhood insights and practical information to enhance guest experiences throughout their Key West visit.
Travel Insurance
We offer optional travel insurance plans to protect vacation investments against unforeseen circumstances. Coverage options include trip cancellation/interruption protection, medical emergencies, and travel delays. Our insurance partners provide customizable policies with clear terms and straightforward claims processes to give guests peace of mind when booking their Key West getaways.
Event Planning
We specialize in creating memorable Key West experiences for weddings, anniversaries, and corporate events. Our event planning services include venue selection, vendor coordination, and customized accommodation packages. With deep local connections and event logistics expertise, we ensure seamless execution of celebrations across our diverse property portfolio and island venues.
People
Roberta Lowe
Co-Founder
Roberta Lowe co-founded Rent Key West Vacations in 1996, bringing decades of local rental market expertise. She established the company's long-term property management division, leveraging her deep understanding of Key West's real estate landscape to build trusted relationships with property owners across the island.
Dawn Thornburgh
Co-Founder
Dawn Thornburgh co-founded Rent Key West Vacations with Roberta Lowe in 1996. As a real estate specialist, she developed the company's sales and management operations while maintaining focus on quality standards. Her industry connections helped establish the company's reputation for reliable, high-standard vacation rental services in Key West.
Paul Hayes
President
Paul Hayes became managing partner of Rent Key West Vacations in 2000, growing the company from 20 to nearly 80 properties. As Florida VRMA board president from 2005-2007, he implemented modern marketing strategies and operational improvements that strengthened the company's position as Key West's leading vacation rental provider.
Dean Carlson
Co-Owner
Dean Carlson co-owns Rent Key West Vacations with Paul Hayes since their 2000 acquisition. He contributes strategic oversight to property acquisitions and guest experience initiatives. His background in hospitality management, including The Mermaid & The Alligator Bed & Breakfast, informs the company's service excellence standards.
Questions
How do I book a vacation rental?
Book directly through our website by selecting dates and property preferences. Our reservation specialists are available at 1-800-833-7368 for personalized assistance with property comparisons and booking confirmations.
What amenities are included?
All rentals include fully equipped kitchens, premium linens, and laundry facilities. Many properties feature private pools, hot tubs, tennis courts, and proximity to Key West attractions like Duval Street and Hemingway House.
What is your cancellation policy?
Cancellation policies vary by property. Detailed policy information appears during booking and in your confirmation email. We recommend purchasing travel insurance for added flexibility.
Are pets allowed?
Some properties accept pets with prior approval. Filter rentals by 'PET FRIENDLY' category or contact our office directly to discuss specific requirements and any applicable fees.
Do you offer travel insurance?
Yes, we provide optional travel insurance plans through trusted providers. Coverage options protect against trip cancellations, medical emergencies, and travel disruptions. Insurance can be added during the booking process.
How are properties maintained?
We maintain rigorous quality standards through regular inspections and maintenance protocols. Our property management team ensures all rentals meet cleanliness and functionality requirements before guest arrivals.
Reviews (4)
Carrie Ortgiesen
Jan 04, 2022
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We love this business. We've used them for 4 vacations to KW. Very efficient and friendly. Highly recommend this company.
Maria Janke
Dec 24, 2021
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The condo was incredible! Good value, great view, the pool was awesome, and easy process to rent the condo.
Liz Brooks
May 16, 2021
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The house was lovely and our stay was awesome. Unfortunately, the house was broken into the last night we stayed. Many valuables were taken in the process. When called about the issue, the company questioned and subtlety accused us of lying about the burglary. No compensation, cooperation or apologizes were giving to us. A police report was filed, and we were informed this is a ongoing issue in the neighborhood.
They did list out strict instructions about locking all doors and valuables in a safe even while sleeping. They have fake cameras set up, and no security system. I will never stay with this company again, as I would never feel safe on their properties.
They did list out strict instructions about locking all doors and valuables in a safe even while sleeping. They have fake cameras set up, and no security system. I will never stay with this company again, as I would never feel safe on their properties.
Madison Campbell
Jan 29, 2021
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Rent Key West Vacations is thorough and professional. Checking in and out was so smooth with all the instructions perfectly laid out for us. The condo was super clean along with the complex. We will use them again and will recommend our friends/family to use them.
