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Jessamine Dream
Lakefront Duplex · Orlando, Florida · Sleeps 16

Jessamine Dream

A seven-bedroom duplex right on Lake Jessamine — two full kitchens, a private pool with cold plunge, hot tub, sauna, and a fishing dock, five minutes from Downtown Orlando.

7Bedrooms
3Baths
16Sleeps
2,892Sq Ft
LakeFishing Dock
Book Direct & Save from $332 / night · book direct & save
Jessamine Dream Jessamine Dream photo Jessamine Dream photo Jessamine Dream photo Jessamine Dream photo
The Estate

One lakefront home. Two of everything.

Jessamine Dream is a true duplex: separate upstairs and downstairs units, each with its own kitchen, living room, and dining area — so big groups spread out instead of stacking up. Between them sits the good stuff: a private pool with a cold plunge, a poolside hot tub, a sauna and weight room, a fire pit, bocce ball, and a putting green. Fishing poles and paddleboards are included for the dock, and jet-ski rentals deliver right to the lake. All of it five minutes from Downtown Orlando — and yes, the owners have both hit buzzers on American Ninja Warrior.

Video Tour

See Jessamine in motion

Highlights

What makes Jessamine unforgettable

Poolside hot tub
Poolside Hot Tub
Sauna
Sauna & Gym
Game room
Game Room
Dock on Lake Jessamine
Fishing Dock
About the Estate

Built for groups that want their own space

Each floor lives like its own home — full kitchen, living room, and dining on both levels, with seven bedrooms between them including a downstairs tropical master, the detached Harry Potter twin room, and an upstairs king suite. The game room brings a pool table, ping pong, and arcade basketball; the yard brings the fire pit, putting green, and bocce court; the dock brings sunrise fishing on Lake Jessamine.

Want just one floor? The Upstairs and Downstairs units can also be booked individually.

Read more ›
Amenities

Everything the group needs — on the lake

Pool & Wellness

  • Private pool (optional heat) with cold plunge
  • Poolside hot tub
  • Sauna & weight room
  • Fire pit · bocce ball court · putting green
  • Outdoor grill
  • Extra pool towels provided

The Lake

  • Direct lakefront on Lake Jessamine
  • Fishing dock — poles provided
  • Paddle boards included
  • Boat & jet-ski rentals nearby (delivered to the lake)
  • Dock & outdoor lights on timers

Inside & Practical

  • Two fully equipped kitchens (duplex)
  • Two washer & dryer sets
  • Game room — pool table, ping pong, arcade basketball
  • 55″ HDTV with Roku · free Wi-Fi · workspace
  • Free parking for up to 6 cars
  • Pet-friendly (per-pet fee)
The Bedrooms

Seven bedrooms across two floors

A downstairs unit, an upstairs unit, and one detached surprise — a living-room futon brings total sleeping to 16. Tap a room to explore it.

2 photos
Downstairs Tropical Master
King bed · Sleeps 2
1 photo
Mural Room
Queen bed · Sleeps 2
1 photo
Downstairs Tropic Room
Queen bed · Sleeps 2
2 photos
The Harry Potter Room
Two twin beds · Sleeps 2
1 photo
Upstairs Master Bedroom
King bed · Sleeps 2
1 photo
Upstairs Bedroom 1
Queen bed · Sleeps 2
1 photo
Upstairs Bedroom 2
Full bed · Sleeps 2
Good to Know

The details, up front

Stay Basics

  • Check-in 4:00 PM · Check-out 10:00 AM
  • Sleeps up to 16 overnight guests
  • Free parking for up to 6 cars
  • Quiet residential neighborhood — please respect neighbors and marked private areas

Deposit & Add-ons

  • $600 security deposit, held 2 days before arrival
  • Pool heat optional — added for the full stay
  • Pet-friendly — per-pet fee applies

House Rules

  • No parties or unauthorized events
  • Quiet hours after 10 PM
  • Exterior security cameras on property
Read more — full house notes ›
Groups & Gatherings

Reunions, golf trips, girls’ weekends

The duplex layout is the trick: families and friend groups get togetherness by the pool and privacy on their own floors. Guests use Jessamine for family reunions, golf trips, and long lakefront stays year-round.

A quick, friendly heads-up on group size. The home sleeps 16 overnight. Larger gatherings need prior approval — tell us your plans and we’ll help you make them work. Unauthorized parties forfeit the security deposit.
Guest Reviews

Rated 4.8 by the groups who stayed

All 142 five-star reviews, unedited — from Airbnb, Vrbo, Google, and direct guests. See reviews for all our homes ›

★★★★★

AMAZING!!!!!!!!!!!!!!!!!!!!!! I can’t wait to go back. Was worth leaving CT. I highly recommend this air bnb to everyone!!!!!!!!!!!!!!!!!!! I did not want to leave . The house is beautiful from every detail in the house . The pictures don’t do it justice, it’s better in person .

Verified guestvia Airbnb
★★★★★

Austin is a super host, alwayes responds fast with action. The house is great and all mentioned immunities are as described and in good condition, location is super in a nice quiet neighborhood. Stayed there for more than a month, this proves what I said. For sure will stay again.

Verified guestvia Airbnb
★★★★★

Austin was a great host. Prompt responses and easy check-in.

As for the place, it was exactly what we wanted in our stay. Comfortable beds/couches, foosball table, pool, diving board, and beautiful backyard. Place was clean when we arrived and comfortable for the entire group.

Verified guestvia Airbnb
★★★★★

The location is so beautiful, unfortunately we didn’t get to experience sitting out on the porch because it was freezing but it would have been extremely peaceful. Austin was also very easy to get ahold of. He also check in half way through the stay. Would definitely recommend 10/10

Verified guestvia Airbnb
★★★★★

We had a fantastic stay here! The place was spotless and well maintained. We especially enjoyed the hot tub, pool, and fire pit. The host was extremely responsive and helpful throughout our stay. The location was also great, just south of downtown Orlando. Highly recommend!

Philip Wvia Vrbo
★★★★★

A very nice house in a great location only about 10 minutes from the downtown area. Austin was easy to contact but there was nothing with the house that needed his attention. The hot tub was very nice to relax in and both the hot tub and the pool were very clean. I’d recommend staying here.

Verified guestvia Airbnb
Availability & Booking

Book direct — the best rate, every time

Real-time availability for Jessamine Dream. Booking direct with Orlando Area Luxury Rentals means the same dates at a better price than the listing sites — no extra traveler fees.

Already bookedAll other nights available
Location

Five minutes from downtown, a world away on the water

5355 Jessamine Ln, Orlando, FL — directly on Lake Jessamine, 5 minutes from Downtown Orlando, 15 from Orlando International Airport, 20 from Universal and the Convention Center, and 22 from Disney.

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