Exceptional vacation homes,
handcrafted for beautiful memories.
A family-run collection of premium, curated short-term rental properties offering five-star comfort and ultimate peace of mind.
A boutique approach to exceptional short-term stays.
At Jolly Homes, we believe that a truly remarkable vacation starts with a home that has its own unique soul and style. That's why we don't manage hundreds of generic listings. Instead, we own and operate a highly curated, family-run portfolio of premium properties.
Each of our homes has been meticulously designed and renovated within the last year, ensuring that nearly everything is brand new. From pristine historic estates in Kentucky Horse Country to sunny pool homes steps from Florida's Gulf coast, we deliver five-star hospitality with the warmth of a family host.
Featured short-term rentals.
Explore our family-run collection of extraordinary properties. Click through on any teaser to view comprehensive availability, photo galleries, and book your stay via VRBO.
Jolly Beach Walk
Brand New 5-Bedroom Pool Home a Short Walk to the Gulf
Bedrooms
5
Bathrooms
4.5
Sleeps
10
Rating
9.8/10
Steps from the soft white sands of the Gulf of Mexico and the brand new Margaritaville Resort, The Beach Walk is a newly built luxury haven on Fort Myers Beach. Crafted for multi-generational families and groups, it features soaring multi-level balconies, private tropically-landscaped heated pool, and elegant coastal-modern finishes.
- 1-minute stroll to the sandy Gulf of Mexico beaches
- Private resort-style heated pool with covered patio
- Steps to restaurants, shopping, and Times Square
- Spacious game room and high-end professional kitchen
Jolly Historic 1850 Mansion
Historic 1850 Towering Italianate Mansion in Horse Country
Bedrooms
4
Bathrooms
3
Sleeps
10
Rating
9.8/10
Step into Kentucky history with the last known Italianate Villa in the state. Meticulously restored to its 19th-century grandeur while integrating top-tier modern luxury, the Basye House is a secure, gated 1-acre private estate nestled in the heart of Lexington's Horse Country.
- Just 2 minutes from the world-famous Kentucky Horse Park
- Meticulous, top-to-bottom designer renovation in 2025
- Fully gated and fenced private estate grounds
- 10 minutes to downtown Lexington, Rupp Arena, and Keeneland
Jolly Beach Dream House
Oceanfront luxury, private dock, and stunning Gulf of Mexico sunsets.
Bedrooms
4
Bathrooms
5
Sleeps
8
Rating
10/10
Built by Barry and Susan Jolly for their family, this incredible beachfront home features a private 100ft dock, swimming pool and hot tub feet from the ocean, sunset bar with views of Sanibel Bridge, an elevator, three lanais, and a Tiki Hut Boat pickup.
- Estero Boulevard Beach features beautiful public sandy beaches just steps away.
- Times Square is a lively pedestrian district filled with dining and shops.
- Key West Express offers daily high-speed ferry cruises to Key West.
- Estero Bay Preserve State Park features protected wetlands and scenic hiking trails.
Jolly Riverview Cabin
Ohio River views, horse country serenity, and unmatched group comfort.
Bedrooms
4
Bathrooms
3.5
Sleeps
12
Rating
9.8/10
This absolutely gorgeous Log Cabin Lodge accommodates up to 12 persons comfortably. Features a wrap 360-degree porch offering spectacular views of 10 miles of the Ohio River, secludend horse country privacy, and modern family amenities.
- 360-degree wrapping porch with an Ohio River Sunset bar
- Spacious kitchen and dining area with seating for 12.
- Entertainment basement with a custom bar, arcade games, and pool/shuffleboard tables.
- Spacious game room and high-end professional kitchen
Why stay with Jolly Homes?
We own and manage our portfolio to ensure your family enjoys an immaculate, comfortable, and completely stress-free getaway.
Handpicked Premium Properties
We only host properties that meet our strict standards for architectural character, premier locations, and grand design details.
Trusted Professional Care
Every property is professionally cleaned, safety-inspected, and maintained by our localized high-touch operations team.
Seamless Family Hospitality
As a family-run business, we provide personalized support from booking to departure, making sure you feel completely taken care of.
Have questions or booking a group stay?
Get in touch with us directly for multi-property bookings, special accommodations, or direct inquiries.