Holiday houses in Winter Springs

Guest suite in Casselberry

4.88 out of 5 average rating, 51 reviews

Comfortable and quiet place

Forget your worries in this spacious and serene space, we offer our guests k cups coffee(Victor Allens), sweteners (splenda) and "Oasis Bliss" personal care amenities( shampoo,conditioner, body lotion, bar soap).Private kitchen and bathroom. Also located less than an hour to Disney and Universal parks. Many restaurants and shoping centers around the area, 15 miles- 20 mins to "Orlando Sandford International Airport". Feel free to ask questions and our family will be in contact with you, thanks

4.88 out of 5 average rating, 562 reviews

Bungalow in Maitland

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.

4.97 out of 5 average rating, 108 reviews

Guest suite in Longwood

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the backyard and NON Heated Pool with your hosts if we are home. Between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 31". We are not Handicap Certified but most wheelchair guests do not have issues. Grab bars in the bathroom.

4.98 out of 5 average rating, 229 reviews

Guest suite in Sanford

The Secret Sanctuary in Sanford, 5min from Airport

Welcome to your quiet, spacious, and private sanctuary. Enjoy all new appliances in the full size kitchen, a 50” flat screen TV, and a shaded outdoor area surrounded by greenery. It is located only minutes from the Orlando Sanford International Airport, Historic Downtown Sanford’s restaurants and shops, Lake Monroe’s scenic waterfront, and is centrally located between Florida’s beaches and the amusement parks. **Space is cleaned with EPA approved cleaners, including high touch surfaces**

4.92 out of 5 average rating, 411 reviews

Guest suite in Oviedo

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and guests have complete privacy. There are no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge , microwave, TV, Wifi and access to non-heated swimming pool. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Universal Theme Parks: 27 miles Disney: 40 miles

4.94 out of 5 average rating, 108 reviews

Villa with Guest House & Pool-Patio

Welcome to this Amazing House Pool-Patio with 4 Bedrooms + 2 Bathrooms and optional guest house. Luxury and true gem with covered summer kitchen, covered pergola, garage for two cars and a large driveway. 30 Minutes distance to Universal, Sea World, Volcano Bay and others. UCF in 15 minutes and Daytona beach/Cape Canaveral in 50’. Great restaurants and shops. The house is conveniently located and accessible for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD

4.94 out of 5 average rating, 126 reviews

Bungalow in Sanford

The Golf-view House (Entire House, King bedroom)

This 2/1.5 house is private, clean, and cozy. The open kitchen features stainless steel appliances and provides all necessary cooking wares. The spacious dining/livingroom area receives enough sunlights through the picture windows. Enjoy beautiful golf course view while sitting at the dining table and/or on the humongous outside deck. There is an outdoor dining area and grill on the deck. The house is within 45 minutes from theme parks (Disney & Universal) and beaches (Daytona/New Smyrna).

Guest suite in Casselberry

4.91 out of 5 average rating, 89 reviews

Orlando, spacious, quiet, centrally located, suite

This suite includes private entrance, living room, kitchen with utensils and cookware, one bedroom with king bed and private bath. Third and fourth persons may be accommodated with recliner that lays flat into a queen-size bed in living room. Also a queen size air mattress and portacrib is available. Excellent location for Disney, Universal, SeaWorld, and beaches. Approx. 35 min. to Disney; 27 min. to Universal; 23 min. to convention center; 45 min. to beach; and 35 min. to Airport.

4.96 out of 5 average rating, 276 reviews

Home in Oviedo

Cute cottage near UCF & trails. No cleaning fee

Our cottage is nestled behind Oviedo’s oldest home. The cottage boasts lots of windows with a beautiful view of the outdoors. Inside the cottage is a queen-size bed, table for 2-4, kitchenette with refrigerator, toaster and microwave, TV with Netflix and Prime, plus WiFi. There is a tall claw foot tub which can be difficult for people with mobility issues. The cottage is connected to the main house but has its own entrance and guests have complete privacy. There are no shared spaces.

4.97 out of 5 average rating, 117 reviews

Guesthouse in Lake Mary

Sunset Cottage in Lake Mary, Florida

Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

4.93 out of 5 average rating, 114 reviews

Guesthouse in Sanford

Suite Retreat

Avoid blah hotels with high prices and stay in this luxe new apartment suite! It’s a perfect retreat in Central Florida. Located a short drive to activities, restaurants, & shops in Lake Mary or downtown Sanford - 45-55 min to Orlando theme parks or the beaches of New Smyrna. Ideal for a couple’s retreat or a getaway for one. Guests use office space designed for comfort & productivity. A cozy chair begs readers to curl up and read. The outdoor canopy hosts breakfast with birdsong!

4.98 out of 5 average rating, 106 reviews

Spacious 3 BR Home Perfect for Orlando Getaway

Relax with friends or family at this peaceful parkside home, while enjoying everything that makes Central Florida so special. From Disney and Universal Studios to Downtown Orlando. Entertainment is just minutes away in either direction with an abundance of shopping and dining options to choose from. Our family absolutely loves this area! We have a recommendation for just about anything and are excited to share this home with you!

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Other great holiday rentals in Winter Springs

4.97 out of 5 average rating, 116 reviews

Guesthouse in Lake Mary

Cozy Cottage in the heart of Lake Mary

VictoriaRating, 5 stars1 month ago

Super clean, comfortable and safe. We loved our stay. The only issue we had was out of Maricela's control which was the loud cars and street noise throughout the night. But there was a white noise machine provided, which really helped. Other than that, everything was perfect!

Guest suite in Winter Springs

4.92 out of 5 average rating, 124 reviews

Modern Guest Studio 15 mins from SFB Airport

KarenaRating, 5 stars2 months ago

I stayed here with another adult and three babies, and we all fit comfortably. It’s so cozy and private. My only complaint that has nothing to do with the host cause she was amazing. Was the height to get into the bathroom. that should be listed on here if your handicapped, it would be difficult to get into the bathroom . Other than that perfect place!!💜

4.89 out of 5 average rating, 63 reviews

Moxy Luxe Vacation / Heated Pool/ King Bed Ste

NelsonRating, 5 stars1 week ago

Enjoyed our stay. Home was just as pictures advertised. Really quiet and peaceful neighborhood. I recommend this place.

4.96 out of 5 average rating, 338 reviews

Guest suite in Lake Mary

Stylish & spa like Getaway - peaceful garden suite

LyndaRating, 5 stars1 month ago

Such a wonderful stay ! We loved it completely. The BATHROOM was the highlight of this place. It’s absolutely wonderful, beautiful and spacious. The entire space was beautiful and spacious. The bed and everything else was very comfortable. Perfect for a solo traveler or couple. The hosts were also so kind as to leave the lights on for when we arrived since we arrived very late. It made our experience so easy and we felt like we were arriving at home. I will definitely be booking this place the next time I’m in the area. Highly recommend this place to anyone who needs a peaceful and relaxing vacation.

4.91 out of 5 average rating, 11 reviews

Home in Winter Springs

Pure Vida - Your home away from home!

KarenRating, 5 stars1 month ago

There was absolutely nothing that needed improvement!

4.86 out of 5 average rating, 7 reviews

Tiny home in Sanford

Guest House

LynnRating, 5 stars1 week ago

Lorraine's place was perfect for me. I needed a place to chill for a week! Hopefully I was a good guest.

5 out of 5 average rating, 5 reviews

Home in Winter Springs

Cozy home - Ping pong - Close to Disney

JovaniRating, 5 stars1 month ago

Very cozy stay! Felt right at home! Very peaceful neighborhood, well easy access to things in Orlando. Wish we stayed longer to truly enjoy all the amenities!