Holiday rentals in Lake Osceola

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Top-rated holiday rentals in Lake Osceola

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Top guest favourite

Guest suite in Orlando

4.98 out of 5 average rating, 398 reviews

A SUITE RETREAT with a Garden View in the City

A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

Guest favourite

Home in Winter Park

4.93 out of 5 average rating, 123 reviews

A Rare Jewel in the heart of Winter park. Can walk

This lovely 3 bedrooms, 2 bath house is located in the most desirable area of Winter Park. Only few steps from Park Ave. You can walk to all the restaurants, Wine room, coffee shops, stores, art galleries, Museum, Park, Rollins College, Winter Park Community Center. Its only 25 minutes drive to the airport, 45 minutes to the beach, and close to family-friendly activities, nightlife, public transport. This house is great for families, couples, solo adventurers, business travelers, and big groups.

Top guest favourite

Tiny home in Orlando

4.96 out of 5 average rating, 295 reviews

Lake View from King Bed+Free Bikes+Kayaks+Espresso

The Perfect Couple’s Getaway❤️ (😊 read our reviews) ‼️NO BOOKING FEE‼️ We Pay All Fees - Espresso Machine☕️ - Couple’s Rain Shower - Heated King Bed - Lake Views from Bed - Hammock in Garden - Grill+Utensils - FREE Bikes+Kayaks+Paddle Boards - Private Garden Yard Seating Wake up to epic lake views from your king bed. Sip strong Cuban espresso, then launch a kayak or paddle board into calm waters—or bike into one of three charming nearby towns: Winter Park, Baldwin Park, or Downtown Orlando.

Guest favourite

Flat in Orlando

4.93 out of 5 average rating, 206 reviews

College Park/Winter Park separate 1 bed/bath 32804

255 sq ft duplex- w/ queen bed, workspace, kitchenette, large bathroom, private entrance & yard area. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. No cleaning fee $20 pet fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 2 mi

Guest favourite

Loft in Orlando

4.92 out of 5 average rating, 583 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.

Top guest favourite

Place to stay in Orlando

4.98 out of 5 average rating, 101 reviews

Hip RetroModern Lakefront Cabana w/ EV Charger

The Kiwi Cabana is a modern euro-style studio that offers the best in location, comfort, and ambiance! Relax with a glass of wine on the patio or dock & enjoy a gorgeous sunset on the lake. Light the fire pit and fire up the grill for a romantic evening. Luxe Queen Murphy Bed. Wifi. Cable. Outdoor Lighting & Sound System. Spacious Leather Sectional. Multiple Coffeemakers. Dishwasher. Microwave. CounterTop Oven. Electric Vehicle Charger at Dedicated Guest Parking Space. STR License #1009857

Guest favourite

Flat in Winter Park

4.9 out of 5 average rating, 152 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.

Top guest favourite

Guest suite in Orlando

4.96 out of 5 average rating, 199 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Top guest favourite

Tiny home in Orlando

4.97 out of 5 average rating, 769 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.

Guest favourite

Cottage in Winter Park

4.94 out of 5 average rating, 403 reviews

Winter Park Pearl 6 min drive to historic Park Ave

This Winter Park cottage was built in 1954 with original hardwood flooring. Take a 5 min drive to and through historical Winter Park to access shops and restaurants on the coveted Park Ave. It is the perfect central location to access beaches, Universities, Orlandos events, and the best restaurants. The house is tucked away into a quiet neighborhood with lots of sleepy old big oaks. If you have any questions I am always available, so please ask. My response time is immediate!

Top guest favourite

Guest house in Orlando

4.93 out of 5 average rating, 248 reviews

Bungalow Near Epic Universe and Downtown Orlando!

Discover our charming cottage behind our bungalow in Downtown Orlando's College Park - conveniently located near Epic Universe and the Disney parks! Enjoy urban living with a small-town vibe, biking along tree-lined streets to restaurants, shops, breweries, and farmers markets. Private access, yard, and driveway and a beautiful park across the street! Conveniently access Winter Park (10 mins), Downtown Orlando (10 mins), I4 (2 mins), Disney and Universal (15-30 mins).

Top guest favourite

Treehouse in St. Cloud

4.96 out of 5 average rating, 987 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.