Waterfront holiday rentals in Osceola County

4.96 out of 5 average rating, 301 reviews

An aerial view of the resort reveals a scenic layout surrounding a sparkling blue pool and vibrant water slides. Palm trees line the poolside area, where lounge chairs are arranged around the water's edge. The lush greenery and nearby lake add a natural touch to the inviting ambiance.

Townhouse in Kissimmee

*LAKEVIEW* Resort 4m Disney! Private Spa Wi-Fi

Welcome to our personal vacation home, Old Town Oasis! Beautiful LAKEVIEW property in Regal Oaks Resort! Coffee, Nespresso, tea, free Wi-Fi! It's close to the theme parks and everything that Orlando has to offer! Come relax in your own private spa after a long day at the parks, or enjoy the resort water slides, heated pool, pool side games & tiki bar with food & drinks, arcade games in Clubhouse and more. If you're up for more fun, walk to Old Town next door! Our place is BABY and KID FRIENDLY!

4.96 out of 5 average rating, 105 reviews

A bright living area features a light-colored sofa complemented by colorful accent chairs. A patterned area rug adds warmth to the space, which includes a ceiling fan and large windows allowing natural light. A blend of greenery and decorative items enhance the inviting atmosphere.

Home in St. Cloud

Lakefront home near Disney/Beach

Relax after a long day visiting the beaches, Disney, or springs in this peaceful lakefront home. Enjoy your morning coffee on the front patio overlooking the lake or wind down with a glass of wine underneath the pergola soaked with tropical flora. A paved walking path is just a few steps from the front door with quick access to the local marina. Downtown St Cloud is minutes away where you can enjoy local eats, drinks, shopping and other amenities! 30 minutes from Disney, an hour to the beaches.

4.97 out of 5 average rating, 189 reviews

The exterior of the barn showcases a rustic wooden facade beneath a metal roof. A porch with seating options invites relaxation, while the neatly maintained yard features green grass and landscaping. A driveway leads to a side garage, enhancing the property's charm and accessibility.

Barn in St. Cloud

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

4.86 out of 5 average rating, 207 reviews

A private pool is framed by a screened enclosure, featuring a gentle waterfall and bordered by comfortable lounge chairs. The serene lake view is visible beyond the pool, complemented by lush greenery lining the shore.

Villa in Kissimmee

Near Disney Gated LakeView Pvt Heated Pool

LIMITED OFFER! FREE CLEANING FOR BOOKING 10 DAYS+ IN NOV-DEC! LOWEST CLEANING FEE! Miltary dscnts. New Pool Heatr, Dolby ATMS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & Lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

4.88 out of 5 average rating, 279 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

4.98 out of 5 average rating, 210 reviews

The living area features a modern sectional sofa with colorful throw pillows in vibrant red and yellow. A matching ottoman sits in front, accompanied by stylish side tables with lamps. Bright blue walls create a lively backdrop, enhanced by a large abstract painting and adjacent dining space.

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

An outdoor pool area is enclosed by a screened lanai, featuring a clear blue pool surrounded by sun loungers. The serene waterfront view is visible through the mesh, with lush green landscaping in the background.

4.89 out of 5 average rating, 101 reviews

Smiling Disney Oasis

Relax with the whole family at this peaceful, Smoke free , waterfront, remodeled, pool home with a game room thats just 12 miles from Disney. HEATED POOL OPTION This waterfront home which is located in beautiful Crescent Lakes in Kissimmee has a large pool area to enjoy the sun, a game room for the entire family to make fun memories ,and more. 3 bed, 2 bath. The community has basketball, tennis courts, walking trails, and a playground. This home is also child friendly with a pack n play.

4.93 out of 5 average rating, 136 reviews

Home in Lake Wales

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

4.92 out of 5 average rating, 111 reviews

A two-story, tropical style home is showcased, featuring a vibrant exterior in warm shades. A Tesla is parked prominently in the driveway, with lush palm trees and greenery flanking the entrance. The garage is accessible, contributing to the property's inviting curb appeal.

Home in Haines City

Luxury Tropical Themed Villa With Lake View!

Just a half-hour from Disney and other major theme parks, this beautiful Tropical style home has a sunset lake view and was recently renovated with brand new furniture! The house resides comfortably in a gated community with 4 bedrooms and 3 bathrooms in a 2-story, 1700 square foot tropical setting! A private heated pool and Tesla charging is also accessible at the home. The Southern Dunes community boasts a large public golf course within a few minutes walk through the neighborhood!

A single-story home is showcased with a light gray exterior and a dark garage door. Lush green grass surrounds the front, complemented by palm trees and shrubs. The driveway leads to the entrance, under a clear blue sky with a few clouds.

4.9 out of 5 average rating, 169 reviews

Peaceful Waterfront Retreat, Close to Everything!

Beautiful 4br peaceful lakefront home in safe, quiet community. Close to major shopping and restaurants! Just a short drive to the Turnpike and 417 highway, close to Disney, Seaworld, Medical City, Lake Nona and the VA Hospital. Comfortable space with smart TVs and central AC. Fully equipped kitchen. Split floor plan perfect for families and friends. The master bedroom faces the rear of the home, large windows allowing natural light to enter the home all while enjoying your waterview!

4.91 out of 5 average rating, 102 reviews

A large stilt house is portrayed above the serene waters of Kissimmee River, surrounded by lush greenery and lily pads. The structure features a wide porch and multiple windows, reflecting a rustic charm with the sky scattered with clouds in the background.

Home in Lake Wales

"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!

A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.