Vacation rentals in Lake Osceola

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Top-rated vacation rentals in Lake Osceola

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 144 reviews

Lou’s Garden Hideout

Welcome to Lou’s Garden Hideout, a private retreat tucked away in one of Orlando’s most charming neighborhoods. Just steps from Harry P. Leu Gardens, this cozy suite features a comfortable queen bed, private bathroom, Netflix, fast WiFi, coffee station, microwave, mini fridge, and free parking. Enjoy a peaceful stay while being minutes from Downtown Orlando, Winter Park, hospitals, restaurants, shopping, and world-famous attractions. Relax, recharge, and make yourself at home.**FREE WIFI NETFLIX

ValueFamilySolo travel

Guest favorite

A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.

Home in Orlando

4.96 out of 5 average rating, 170 reviews

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

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Superhost

Treehouse in Geneva

4.89 out of 5 average rating, 1,152 reviews

Treehouse at Danville

Private Getaway seen on Netflix' Most Amazing Vacation Rentals! Fulfill your dream of staying in a tree house! For safety reasons, this venue is for adults only. We do not allow children or pets. The Treehouse has a tree trunk elevator, private shower, air-conditioning, and real toilet inside so that you can bring your significant other(no compost toilet here). This 18 foot yurt has accent lighting to create the mood of living in the trees on a starry night. Danville is a glamping experience.

LocationValueNearby

Top guest favorite

A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.

Bungalow in Maitland

4.88 out of 5 average rating, 627 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

ValueFamilyWifi

Guest favorite

A modern living space is highlighted by a plush grey sofa and mid-century styled furniture. A large window invites natural light, showcasing views of the outdoors. Decorative elements, including a small plant and artwork, add character to the room while maintaining a clean aesthetic.

Loft in Orlando

4.92 out of 5 average rating, 691 reviews

Contemporary Loft Near Downtown

Conveniently located between the foodie-friendly Milk District and Downtown Orlando, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is only 20 minutes away, Disney is 35 minutes, MCO 20 minutes.

LocationValueLong stay

Top guest favorite

A charming lakefront cottage is viewed from across the water, showcasing its blue exterior. The porch area includes a deck with seating, and two light-colored lounge chairs are positioned on the grassy lawn, surrounded by lush greenery and trees.

Cottage in Altamonte Springs

4.99 out of 5 average rating, 155 reviews

Charming Private Lakefront Cottage Retreat

You can fully relax in this adorable lakefront cottage. We're sure you'll enjoy all of the wonderful amenities this peaceful property has to offer. Our incredibly unique cottage is nestled under a large grand oak tree and tucked away behind climbing jasmine vine clad fencing and security gates. Inside, you will find a new remodeled fully stocked kitchen and luxury bathroom. Our cozy cottage has all the comforts of home and more. Reserve your stay today and enjoy this special property.

FamilyLocationLong stay

Guest favorite

Apartment in Winter Park

4.9 out of 5 average rating, 227 reviews

The Lake House

Welcome to the mid-century Lake House. 370 square feet apartment with a private entrance and original terrazzo floors. Located on a quiet residential street on a small lake, and located within a 5-minute drive to anything you may need! Starbucks and Panera are within walking distance, and dozens of other places to eat. Publix, Walgreens, and Sprouts are just around the corner. A short 10 minute drive to the famous Park Ave, in Downtown Winter Park with shopping and gourmet restaurants.

FamilyValueOutdoor spaces

Top guest favorite

Loft in Orlando

4.92 out of 5 average rating, 1,012 reviews

UPSCALE LOFT SPACE CLOSE TO DOWNTOWN.

Tucked right between the charm of Lake Eola Park and the eclectic, foodie-loved Milk District, this space puts you in the heart of Orlando’s most vibrant neighborhoods. With a Full renovation 3/2026, this open floor plan highlighted by floor-to-ceiling windows that flood the space with natural light. When you’re ready to venture out, you’re just minutes from the upscale dining and shopping of Winter Park, as well as the walkable streets, art galleries, and lively energy of Thornton Park.

FamilyLocationLayout

Top guest favorite

A stylish kitchen is equipped with modern stainless steel appliances, including a refrigerator and microwave. A central island features two metallic stools, and the cabinetry is finished in a soft gray. A small potted plant adds a touch of greenery to the space.

Guesthouse in Orlando

4.99 out of 5 average rating, 135 reviews

Location, Location, Location!

Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 min)

ValueFamilyParks

Top guest favorite

The screened-in pool area features a tranquil pool with a soft blue hue, surrounded by white decking. A small table holds a lit lantern beside two lounge chairs, providing a serene space for relaxation under the evening sky.

Home in Maitland

4.98 out of 5 average rating, 130 reviews

Florida Poolside Paradise a Great Place to Unwind!

Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

FamilyLocationCheckout

Guest favorite

A cozy space is illuminated by warm lighting and twinkling string lights. A comfortable bed with decorative pillows is framed by wooden accents. A small seating area features a television and has a view of the garden area with fire pit chairs, creating a relaxing outdoor ambiance.

Tiny home in Orlando

4.97 out of 5 average rating, 885 reviews

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

LocationValueLong stay

Guest favorite

A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.

Treehouse in St. Cloud

4.97 out of 5 average rating, 1,155 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.

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