Holiday rentals in Lake Kissimmee

4.91 out of 5 average rating, 47 reviews

Waterfront Lake Kissimmee House W/ BOAT LIFT

Beautiful & peaceful 2 bedroom, 2.5 bathroom home located right on the South West corner of Lake Kissimmee (off state road 60). Lake Kissimmee is known for its world class fresh water fishing and airboating. House also comes equipped with a covered boat slip with lift for your boat. Right next to Grape Hammock Boat Ramp and Camp and also minutes away from West Gate River Ranch. Perfect whether you’re looking for a fishing trip, family fun filled weekend at the rodeo or just a place to get away.

Guest suite in Haines City

4.92 out of 5 average rating, 87 reviews

1 BR 1BA Lake Apt. Boat slip, Deck, Pets, Laundry

Come wake up to birds singing, looking out your windows to a nice deep water canal view. The canal leads to Lake Hatchineha (great fishing). TVs in every room. Fully loaded kitchen; private entrance. There is a porch, laundry and deck area shared with one other apt. Free laundry . We are 45 min from MCO(airport) 45 min from Disney and 15 minutes to Legoland. Bok Towers is a unique park that is 18 miles away. Star gazing and bicycling or fishing. Pets $35 per trip with a fenced in area for them.

4.98 out of 5 average rating, 197 reviews

Villa in Lake Wales

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, 41 reviews

Lake Rosalie Getaway

Escape the hustle and bustle of life and enjoy a relaxing vacation at our newly remodeled lakefront home in beautiful Lake Wales! Located on peaceful Lake Rosalie, our residence is the perfect isolated getaway, yet still close to popular attractions such as Bok Tower Gardens, Legoland, Lake Kissimmee Park, Westgate River Ranch Rodeo and more! Unique amenities: - Large, upper-story wooden deck - 2 kayaks - Outdoor games, fishing poles - Exercise bike - Office room with printer - New kitchen

4.98 out of 5 average rating, 91 reviews

Lakefront Views! Private Dock! Great Bass 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

4.9 out of 5 average rating, 125 reviews

Cottage in Lake Wales

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.

4.9 out of 5 average rating, 100 reviews

Dome in Davenport

Modern Domes | Pool | Hot Tub- Private Retreat!

Reserve your stay with us now and take advantage of the following amenities: Newly Built- Our facilities are completely new Climate Control- Enjoy cold AC/heat with fans and full insulation for comfort Complete Privacy Pool with pool toys and floats Hot Tub High-Speed WiFi Coffee Bar Hammock for Two Entertainment- TV with Netflix, Hulu, etc. Private Outdoor Shower- Enjoy a hot shower in a secluded setting. Private Fire Pit Variety of Games Secure Location- Gated area with keypad entry

5 out of 5 average rating, 24 reviews

Home in Haines City

Lake Hatchineha Fishing Paradise w/private ramp

WATERFRONT fishermen & airboater's paradise! Peaceful neighborhood in Central Florida on the Kissimmee Chain of Lakes. PRIVATE BOAT RAMP! The house sits on a canal that leads out to Lake Hatchineha which connects to three more lakes for the best fishing around! Our covered boat dock can house three boats w/a fish cleaning station and dock refrigerator. Pet friendly. We are 37 miles to Disney, 30 minutes to LegoLand, Golf course within 10 minutes, and a restaurant a mile away.

Superhost

4.91 out of 5 average rating, 89 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!

4.92 out of 5 average rating, 370 reviews

Tiny home in Babson Park

Lil cedar tiny home, on crooked lake

Newly constructed tiny home.locatedon one of Florida's most prestigious lakes.crooked lake in s central floridais noted for its spring fed,clear water and white sand beaches,as well as it's amazing fishing and boating opportunities.the tiny house sits on 3/4 acre property overlooking crooked lake.the "million dollar view" as it's been called is spectacular at sunrise.the tiny house has an open ,airy, feel,with its comfortable roomy bedroom loft,and all the amenities of home.

4.96 out of 5 average rating, 982 reviews

Treehouse in St. Cloud

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.

Superhost

4.85 out of 5 average rating, 157 reviews

Hidden Gem - Hot Tub/ Fire pit/Hammock/Grill Area

Take it easy at this unique and tranquil getaway. Come and enjoy a piece of heaven with friends and family. Take a soak on the hot tub, fire up the grill, make some smores on the fire, sit back and relax. Close to lakes and state parks. Bring your boat or rent our available kayaks to have a great day at Lake Pierce less than a mile away. Drive 45Mins to Disney and 20mins to Legoland. We'll see you soon! Events Available upon request.

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Other great holiday rentals in Lake Kissimmee

5 out of 5 average rating, 8 reviews

Guest house in Kissimmee

The Forrestry

LoveRating, 5 stars1 week ago

I had a great stay! The place was exactly as described—clean, cozy, and well-maintained. The host was super responsive and helpful throughout my visit. The neighborhood felt safe and was close to everything I needed, which made getting around super convenient. I especially appreciated the little touches like fresh towels, toiletries, and a smooth check-in process. I’d definitely stay here again and recommend it to anyone looking for a comfortable and hassle-free stay!

5 out of 5 average rating, 6 reviews

Home in Haines City

Lake Hatchineha house on canal

EdRating, 5 stars1 week ago

I love this place. Nice big back patio area with great view. Remote controlled boat lift was a big plus. House was nice and clean and very comfortable. Will definitely be back!!!

5 out of 5 average rating, 22 reviews

Home in Lakeshore

Relaxing Villa

LuisRating, 5 stars1 month ago

This place is awesome. Very peaceful and the washer and dryer is a plus. I would recommend this to everyone.

Home in Haines City

5 out of 5 average rating, 4 reviews

Lake Life, Waterfront, Private Boat Ramp, Dock,

DonnaRating, 5 stars2 months ago

This is a beautiful home. it is about 15 miles from any shopping, so it is somewhat remote but with neighbors. it sits on a canal that connects with a large lake. it is part of the chain of lakes. so houses line the canal on both sides. the hostess outdid herself with supplies and making it feel homey and so comfy. we loved it and it was hard to leave!

5 out of 5 average rating, 11 reviews

Reel Simple

ChrisRating, 5 stars2 months ago

Heidi was great, super helpful and always available. Property is amazing and is even bigger than what I expected. Did some fishing and was able to dock my boat in the boat house. Gotta love not putting in and out after sun up to sun down days of fishing. You can gas up from the water at camp Mack as well. I look forward to my next camp Mack trip and staying at Heidi’s beautiful place. Thanks Heidi

5 out of 5 average rating, 8 reviews

Tiny home in St. Cloud

Little House 30 mi To Disney Fun

DanielRating, 5 stars1 day ago

Very cute place! It was very cozy for the night my girlfriend and I stayed there. Can’t recommend enough!

4.94 out of 5 average rating, 52 reviews

Home in Lakeshore

Secluded villa/pool/hot tub/ washer/dryer

SabrinaRating, 5 stars2 months ago

Such a relaxing place to stay! We loved the area, the water and walking paths under the trees. The community is quiet, and we biked around it for miles. The pool is fun and the water temp stays perfect. The villa is cute and neat as a pin. We had coffee on the lanai every morning, and slept great in the bed. Laundry available to us was also a plus! Kitchen is little but has everything you could need. We cooked and ate in for most meals, but also found a couple of great restaurants nearby.