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Vacation rentals in Winter Springs

Vacation rentals in Winter Springs

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winter Springs

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

  • Affordable Room/Office w/breakfast and snacks.
    SUPERHOSTPrivate room · 3 guests · 2 beds · 1 shared bath
    Affordable Room/Office w/breakfast and snacks.

    Location 20 to 30 minutes to downtown Orlando 20 minutes to Sanford, 45 minutes to I-Drive 45 minutes to New Smyrna 45 minutes NORTH of theme park exits on I-4 Common areas living room large porch great room kitchen/pantry. Complimentary breakfast and evening wine. Another room is available in the house with a private office/tv room . It sleeps two.

    What guests are saying:

    “This home and host are both great. The room is so quaint but with so much space. Dorinda goes above and beyond to provide the best experience possible. She provides products and amenities that far exceeds expectations. A great choice!”

  • Oviedo Oasis: 2 bedroom Guest Suite; Private Pool
    SUPERHOSTEntire guest suite · 5 guests · 3 beds · 1 bath
    Oviedo Oasis: 2 bedroom Guest Suite; Private Pool

    Cozy 2 bedroom en suite attached to the main house with private entrance and no shared living space within the home. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge , microwave, TV, Wifi and access to our swimming pool. The home backs up to the Cross Seminole Trail. NO PETS ALLOWED Central to everything: UCF: 5 miles Orlando Airport: 25 miles Sanford Airport: 11 miles Universal Theme Parks: 27 miles Disney: 40 miles New Smyrna Beach: 41 miles

    What guests are saying:

    “I definitely enjoyed my stay. The property has everything you need and it’s wonderful to relax in the pool as well. I was thrilled to find out there was a biking trail within walking distance. The property is located in a somewhat rural and very beautiful area, but also located within minutes of restaurants, gas stations, etc. The bed was really comfy and I did not want to get out of it on the checkout date. I would definitely rent again.”

  • Farmhouse Cottage near UCF,
Trails, & theme parks
    SUPERHOSTEntire cottage · 2 guests · 1 bed · 1 bath
    Farmhouse Cottage near UCF, Trails, & theme parks

    Our farmhouse cottage is nestled behind Oviedo’s oldest home. The cottage boasts lots of windows with a beautiful view of the outdoors and a Koi pond. Inside the cottage is an inviting queen-size bed, table for two, stocked coffee bar, refrigerator and microwave, TV with Netflix and Prime, plus WiFi. In the bathroom there’s a claw foot tub. The cottage is connected to the main house but has its own entrance and guests have complete privacy. There are no shared spaces.

    What guests are saying:

    “This was the best Airbnb experience I’ve ever had. The host thought of everything. Even left lights on leading to the beautiful cottage because we were getting in late. The place was spotless, with snacks and entertainment, along with recommendations for local sights and food. I will definitely be back to stay again and HIGHLY recommend this to anyone looking for a quiet getaway!”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Winter Springs vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Winter Springs

Affordable Room/Office w/breakfast and snacks.
SUPERHOSTPrivate room
Affordable Room/Office w/breakfast and snacks.
Price:$62 CAD/night
Oviedo Oasis: 2 bedroom Guest Suite; Private Pool
SUPERHOSTEntire guest suite
Oviedo Oasis: 2 bedroom Guest Suite; Private Pool
Price:$124 CAD/night
Farmhouse Cottage near UCF,
Trails, & theme parks
SUPERHOSTEntire cottage
Farmhouse Cottage near UCF, Trails, & theme parks
Price:$109 CAD/night
1BR luxury apt centrally located in Maitland
Entire apartment
1BR luxury apt centrally located in Maitland
Price:$64 CAD/night
Beautiful east Orlando pool home welcomes you!
Private room
Beautiful east Orlando pool home welcomes you!
Price:$43 CAD/night
Comfortable Room
Private room
Comfortable Room
Price:$34 CAD/night
Private Room with all essentials in Altamonte 1
Private room
Private Room with all essentials in Altamonte 1
Price:$14 CAD/night
Great location! Private Studio Casselberry FL
SUPERHOSTEntire house
Great location! Private Studio Casselberry FL
Price:$67 CAD/night
Lovely and Peaceful 3 bed Home in Oviedo
Entire house
Lovely and Peaceful 3 bed Home in Oviedo
Price:$95 CAD/night
Room
SUPERHOSTPrivate room
Room
Price:$28 CAD/night
Private room in Lake Mary/Sanford
Private room
Private room in Lake Mary/Sanford
Price:$34 CAD/night
Lux Private Modern Retreat near MCO airport  GATED
Entire condominium
Lux Private Modern Retreat near MCO airport GATED
Price:$14 CAD/night
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