Waterfront holiday rentals in Osceola County

4.85 out of 5 average rating, 210 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 OR MORE DAYS! 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, 281 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.

4.96 out of 5 average rating, 106 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.

4.96 out of 5 average rating, 175 reviews

A lush outdoor water complex showcases a winding lazy river surrounded by palm trees and landscaped greenery. Lounge chairs are positioned alongside the water, providing ample space for relaxation. In the background, a clubhouse and scenic waterfront can be seen under a bright blue sky.

Townhouse in Kissimmee

Disney 5BR • Private Pool Free Heat • Pet Friendly

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

4.97 out of 5 average rating, 190 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

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.

4.98 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

Guest suite in Haines City

A waterfront property is showcased, featuring a wooden exterior and a covered boat slip. Lush greenery surrounds the home, with a fire pit visible in the yard. The structure appears elevated, with a spacious deck above the boat area, providing picturesque canal views.

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

4.97 out of 5 average rating, 142 reviews

Lakeview Luxury Home 9BD|9BA Sleeps20/Near Disney

We have the largest driveway in the entire resort. 6000 SQ ft gated luxury home near Disney.Enjoy the sunset from our pool!Sonoma Resort is a perfect location, only 5 minutes to the LOOP,one of Florida`s finest shopping and entertainment destinations, in the resort it self, you`ll discover a amazing clubhouse with a gym and a large community pool.This 9 bedroom/9 bathroom home is well equipped to accommodate up to 20 guests. Our driveway will accommodate up to 8cars.Come enjoy your vacay Home!

4.93 out of 5 average rating, 138 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

The exterior view showcases a well-appointed home with a paved walkway leading to the entrance. A manicured lawn and driveway provide an inviting atmosphere. An outdoor BBQ grill overlooks a private, screened pool area, surrounded by a peaceful lake view and tropical landscaping.

4.82 out of 5 average rating, 101 reviews

5390 Vacation Sunset House Private Pool Grill

Relax in this calm, stylish and FULLY RENOVATED residential HOME. Enjoy with the whole family our PRIVATE POOL & BBQ GRILL with LAKE VIEW. Located in Kissimmee Florida, in a quiet residential neighborhood. Master Suite with view to Pool & BBQ outdoor area. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 2 car garage, 3 Smart TV's and strong Wi-Fi all around the house. Have unforgettable moments at our BBQ area next to our private screened pool. Sunsets by the lake are breathtaking.