Jessamine Dream Family Rental Home near Orlando

Book a large private home for your unforgettable family vacation, or dream wedding, in FL. We offer exclusive, one of a kind large rental homes with all the amenities imaginable with room for up to 50 guests at our larger properties.

Whether visiting FL for a family vacation, family reunion, or planning an unforgettable wedding – you’ll find the perfect private estate for your needs.

Jessamine Dream Family Rental Home near Orlando

Whether visiting FL for a family vacation, family reunion, or planning an unforgettable wedding – you’ll find the perfect private estate for your needs.

Jessamine Dream – A Lakefront Orlando Vacation Rental for Families and Groups

Enjoy waterfront living without giving up the convenience of a central Orlando location at Jessamine Dream. Located directly on Lake Jessamine, this spacious seven-bedroom vacation rental accommodates up to 16 guests and offers a unique duplex layout with separate living, dining, and kitchen areas on each level. It’s an excellent choice for Orlando family vacations, multi-family getaways, family reunions, golf trips, extended stays, and group vacations.

With two self-contained living areas, Jessamine Dream gives larger groups the flexibility to vacation together while still enjoying additional privacy and personal space. Families can gather around the pool, lake, game room, and outdoor areas, then spread out between the two levels when it’s time to relax.

9 Gigantic Estate Homes So Fun & Relaxing That You Won't Need To Go Anywhere!

Book a family vacation or family reunion for your entire multi-generational family at one of our luxurious estates, each with its own incredible list of amenities that are sure to entertain and please everyone. Whether to select from one of several estates in the Orlando area near all the main theme park and attractions, or our stunning property in Medina, Ohio near Cleveland.

From family vacations, to family reunions, to unforgettable weddings, you’ll find the perfect estate for you and your entire family.

Reviews from our Estate Guests

★ ★ ★ ★ ★

4.8 | Top Rated Service

This house is really cool. Every single room (bathrooms included) are themed. The pool is one of a kind. There’s a ton of games to play, board games, arcade games, video games, laser tag, disc golf, an escape room, karaoke, etc. We really enjoyed watching a movie by the pool under the stars and just had fun. There’s also massage chairs and a sauna which were great ways to relax at the end of the day. The details in this house are everything.

If you’re looking for an incredibly unique vacation rental near Orlando, this sweet themed house is a must! With a ton of uniquely themed bedrooms inspired by iconic treats like Coca Cola, Pepsi, and Hershey’s syrup, each room offers a fun and immersive experience. The highlight is the ice cream-shaped pool, along with a nostalgic arcade perfect for family fun. Whether you’re relaxing by the pool or exploring the whimsical décor, this house is ideal for families or groups of friends seeking a sweet and unforgettable getaway in Florida!

This property was phenomenal and we will have a lifetime of good memories! The hosts are amazing and will help take care of everything you could possibly need!

The Sweet Escape is the perfect spot to get together with family and friends. There is something to do for everyone! We have really enjoyed our stay here. Highly recommended.

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