Guesthouse holiday rentals in Osceola County

5 out of 5 average rating, 14 reviews

The Forrestry

The Forrestry is the ideal launching pad for visits to the parks. Perfectly priced so you can enjoy Disney, SeaWorld, Legoland & Universal's Epic Universe. The garden gate opens to a spacious patio. This cozy retreat is a great room concept. A coffee bar with snacks greets you on entry into the living room, with a comfortable sofa bed and a multi-use table for games and dining. A well-equipped kitchen and laundry room flank it. The bedroom suite has a spacious walk-in closet and bathroom.

4.92 out of 5 average rating, 136 reviews

Cozy & Deluxe studio for 2 near Disney&parks

Welcome to my independent apartment in my house, I have a great location and you can enjoy easy access to popular shops, restaurants and parks from this charming place to stay with a great location. I also offer the ride from/to the airport just for $30 each ride from home. MCO 30 Min Kissimmee gateway Airport 3 miles-7min Osceola hospital 2.7 miles-7min Disney world and Disney parks are 11-12 miles Universal Studios/ aventure Island is 18 miles The Loop Shopping center is 5.7 miles

4.95 out of 5 average rating, 40 reviews

Guesthouse in Davenport

Thousand Oaks Peaceful Studio with Private Pool

Take a break in your private pool and unwind at this peaceful oasis! Escape to this serene studio, just a short drive from the magic of Disney World and Universal Studios. Enjoy the exclusive use of the pool, perfect for relaxation and sunbathing. The house next door is a completely separate unit and does not have use of the pool. If you are traveling with friends and/or family, we also have another studio right next door! Check it out here: https://www.airbnb.com/l/AY7X1u4B

Guesthouse in Lake Hamilton

4.89 out of 5 average rating, 259 reviews

Luxury Cottage Near Legoland & Chain of Lakes

The Old Florida Cottage, in the quaint community of Lake Hamilton, just 5-miles from Legoland, less than an hour from Disney, and minutes away from the only public boat access to Lake Hamilton, is your perfect getaway! Enjoy a fully-equipped kitchen, a luxurious suite and modern bathroom, surrounded by Old Florida decor. We look forward to welcoming you to the cottage, with its own entrance and dedicated parking, located on a quiet street. Your home away from home!

Superhost

4.9 out of 5 average rating, 20 reviews

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

Private Pool Oasis Near Disney – Perfect for Summer! Enjoy a private pool at this cozy 2-bedroom guesthouse, just minutes from Disney, Universal, and Old Town Kissimmee! ☀️ Cool off in your private pool after theme park adventures ⛱️ Relax & unwind in a spacious outdoor area with floaties 🏡 Comfortable & fully equipped for families or couples 🍽️ Full kitchen to prepare meals & snacks before heading out Skip the crowds—book your summer escape now!

4.88 out of 5 average rating, 50 reviews

Guesthouse in Davenport

Charming & Cozy Guest House Minutes from Disney

Experience a stylish stay at this centrally-located gem! Our cozy efficiency guest house in Davenport is just 25 minutes from Walt Disney World. Relax in this beautiful vacation retreat with all the comforts of home. Located minutes from Davenport's main avenue, US 27, near I-4, restaurants, supermarkets, and Orlando's best tourist spots. Enjoy the convenience of self check-in and a private entrance. Book now and make your vacation unforgettable!

4.93 out of 5 average rating, 68 reviews

Guesthouse in Davenport

Tiny Attached Studio with Kitchenette

Explore the allure of our studio, a cozy tiny home situated on the left side of our property. Enjoy the convenience of a fully equipped kitchen. Perfect for Disney, Legoland, and Universal Studios adventures, as well as quick beach getaways. Close to shopping and dining for family fun. Designed for productivity with high-speed internet, a compact workstation, and vibrant lighting. Uncover the magic of your exclusive tiny home experience!

Guesthouse in Four Corners

4.98 out of 5 average rating, 491 reviews

Quiet Room Close to Disney and Attractions

Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.

Superhost

4.81 out of 5 average rating, 57 reviews

Tiny Lakeview Suite Near Disney & Universal

Our cozy Tiny suite offers a stunning lake view right from the bed, thanks to the large sliding windows. Enjoy the sunrise in the morning without even getting up – pure relaxation. You’re just 20-25 minutes away from top attractions like Disney World, Universal Studios, outlet malls, and the airport. Perfect for couples or solo travelers who value comfort and privacy. An ideal retreat after a fun-filled day.

4.98 out of 5 average rating, 83 reviews

Brand new beautiful apartment

Enjoy the simplicity of this quiet, central and cozy place to stay . It is a spectacular studio apartment with independent entrance to the house . And the entire home is available only for guest use . With grill area. 15 min from the orlando airport and 20 min from the parks . Close to outlets and the center convention. Parking is available and if you want a transfer we could also help you

5 out of 5 average rating, 16 reviews

Orange Blossom Apartment

Welcome to the Orange Blossom Apartment - Your Private Oasis! Escape to your own private oasis at Orange Blossom Apartment, a charming and comfortable guest suite nestled within a tranquil home. Enjoy complete privacy with a dedicated entrance, making your stay truly independent and relaxing. Centrally located so you are just a few miles away from all of Central Florida’s major attractions!