
Vacation rentals in Lake Kissimmee
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Top-rated vacation rentals in Lake Kissimmee
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Charming, renovated 1917 Cottage
Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!
4.98 out of 5 average rating, 170 reviews
Adult-Only Retreat w/ Pool & Spa | 18+, Private
🔒⛓️🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)
4.98 out of 5 average rating, 136 reviews
Lake Retreat w/Pool & Hot Tub near Bok tower
Pool & Hot Tub in screened Lanai. Large 4 Bedroom home with Living & Family rooms, 3 dining areas (screened porch that sits 12+). Wood burning fireplace in family room & electric fireplace in primary bedroom. Primary bedroom: en suite bathroom, makeup counter, attached office and 2nd floor balcony with lake views. Stocked kitchen with pots/pans, silverware, cups and plates. Drip & K Cup for coffee, Bonus: french press & moka pot. Bathrooms: plenty of towels, shampoo, conditioner & body wash.
4.86 out of 5 average rating, 100 reviews
2 BR 1 BA Lake House , Boat Slip, Pets, (king bed)
Escape to the perfect, peaceful pet friendly retreat with king bed. We are located on one of the 5 canals on Lake Hatchineha, the first of The Kissimmee Chain of Lakes. Connecting us to The Kissimmee River where you can rent a boat at Camp Mac and drive it home or bring your own boat and park it under cover in one of the boat slips.We are 45 minutes from Orlando airport or an hour from Tampa. 45 min to Disney's Magic kingdom/Universal Studios. 30 min to Legoland. Bok Towers free pass for 4.
4.84 out of 5 average rating, 117 reviews
Lakefront, Dock, 2 Kayaks, near Bok & Legoland
** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS
4.98 out of 5 average rating, 210 reviews
Sunshine on the Lake | Boat Slip+Lakefront Fishing
Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park
4.93 out of 5 average rating, 138 reviews
LakeFront Sunrise Cottage
Catch sunrises or fish at this 2/1 lakefront house with sandy beach and private boat house! This cheery cottage is perfect for sunrises with coffee or exploring beautiful Lake Sebring on kayaks (included with booking). Plenty of parking onsite (bring your boat trailer), you will love this oasis on the lake! We want your stay to be pleasant and carefree so we do not require our guests to do any dishes, laundry, or other cleaning when checking out. Our housekeeping crew will take care of you!
4.98 out of 5 average rating, 190 reviews
The "Little ‘Toa" Ideal for short & long stays!
Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.
4.91 out of 5 average rating, 138 reviews
Lake Denton Diver's Paradise Swim-Dive-Boating
Experience Lake Denton, a crystal clear 50’ deep spring fed diver’s lake where the water is so clear you can watch fish swim beneath you. There is a reason people like Tiger Woods, Whistlin Diesel, Mel Tillis and others have swam here. This family friendly getaway offers a private waterfront setting with unforgettable sunsets from the boathouse. Enjoy swimming, fishing, grilling, water toys and in water volleyball. Kayaks provided, Public boat ramp access. Voted Nicest Lake in Florida
4.87 out of 5 average rating, 146 reviews
"Cutty Shack" Waterfront Kissimmee River House 3/3
"Cutty Shack" is the perfect fishing retreat. It is a 3 bedroom, 3 bath home built by our family in 1969. The Cutty Shack will sleep 6-7. This large stilt home (all living area is upstairs) is situated directly over Kissimmee River and right next door to Camp Mack River Resort. You and your group can enjoy peaceful evenings in the house, or walk next door to grab a drink and watch a "weigh-in". Our family has enjoyed this retreat for five generations and we hope you will too!
4.91 out of 5 average rating, 102 reviews
Linda Casita de Lake Wales
Cute older house with modern amenities. Located right downtown within a block from the playpark, Lake Wailes lake, walking path, and the historic downtown shopping area. All of the appliances in the home are brand new, as well as the washer and dryer. There is a large TV in the living room, as well as one in each bedroom - each with Roku and Netflix. Each bedroom also has a mini split A/C unit to sleep as cold, or hot, as you like. Parking is in the rear covered carport.
4.98 out of 5 average rating, 209 reviews
TreeHouse in the Cloud, (Close toTheme Parks
The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.
4.97 out of 5 average rating, 1181 reviewsPopular amenities for Lake Kissimmee vacation rentals
Lake side house rentals in Lake Kissimmee

Legoland Lakehouse Canoe&Kayak Retreat
4.92 out of 5 average rating, 226 reviews
Lake Letta Lakehouse
4.94 out of 5 average rating, 265 reviews
Lakefront | Boat Access | Pet-Friendly
4.81 out of 5 average rating, 555 reviews
Shady Ln Hideaway Fisherman's Dream Lake Wales, Fl
5.0 out of 5 average rating, 13 reviews
Lakefront 2br w/pier & dock 4,500-ac Lake Rosalie
4.9 out of 5 average rating, 40 reviews
Multifamily home on the water, sleeps 16
4.8 out of 5 average rating, 5 reviews
Lake Rosalie Getaway
4.98 out of 5 average rating, 57 reviews
Just Because Ranch (Westgate RIVER RANCH)
4.91 out of 5 average rating, 54 reviewsOther great vacation rentals in Lake Kissimmee

Wilderness Calls
4.78 out of 5 average rating, 9 reviews
The Shady Oak Shack
5.0 out of 5 average rating, 10 reviews
500ft to Westgate River Ranch/ Disney Universal 1h
4.97 out of 5 average rating, 39 reviews
Home theater & pool table near Disney parks
4.88 out of 5 average rating, 33 reviews
Winter Haven Waterfront Retreat
5.0 out of 5 average rating, 45 reviews
Lake Reedy Resort
4.87 out of 5 average rating, 53 reviews
Lakefront Victorian Hse for Time Travelers & Event
5.0 out of 5 average rating, 59 reviews
Cottage in the Oaks River ranch
4.91 out of 5 average rating, 56 reviewsDestinations to explore
- Miami Vacation rentals
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- Walt Disney World Resort
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- Epcot
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- Kia Center
- Camping World Stadium
- University of Central Florida
- Disney's Animal Kingdom Theme Park
- Tinker Field
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
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- LEGOLAND Florida Resort
- ChampionsGate Golf Club
- ICON Park
- Disney's Hollywood Studios
- Aquatica
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure





