We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Longwood Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $283 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Longwood area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 26 Rentals in Longwood
    Sort by:
    Default
    Longwood
    5 Bedrooms, 4 Bathrooms, Sleeps 50 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Longwood
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Longwood
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Longwood
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Storey Lake Resort and this stunning 4 bedroom, 3 bathroom, 1,914 sq. ft. rental located near the theme parks in Orlando, Florida. This rental has attained the prestigious “Grand” status for having an upgraded professional furniture package. This vacation rental has all the comforts of...
    View all property information
    Location Information
    Longwood, Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    The following rentals are within 10 kilometres of Longwood.
    3 BD Furnished Quaint Altamonte  / North Orlando1 / 10
    (2)Excellent
    Altamonte Springs
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Porch
    • Parking
    • Patio
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    We stayed in this house for about a week and it suited us just fine. It had only one bathroom but we also have only one bathroom and are accustomed to that. The bedrooms were...
    Reviewed 12 June 2016
    We had to make an unexpected visit to the area for a death in the family. Owner was great to deal with especially with such short notice. The house was great. Plenty of...
    See all reviews
    About this property
    Located in Altamonte Springs, near Maitland, Winter Park, just minutes North of Orlando. Giving an expansive selection of Shopping, Malls, Restuarants, and Theatres available within 2 miles. Close to many Golf courses. Just blocks from Interstate 4. 30 minutes to Sea World, Universal and Disney's...
    View all property information
    Location Information
    Altamonte Springs, Central Florida 32750
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MONTHLY RATES For 4 weeks or longer $2200 - $2400. ASK Owner FOR QUOTE! You will love our 1950s home in the Beautiful Bear Lakes Area and we can't wait to welcome our Guests! We purchased this home in January 2012 and transformed it into a beautiful jewel. We put in all the modern conveniences...
    View all property information
    Location Information
    Altamonte Springs, Central Florida 32703
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Bird Nest Retreat1 / 18
    (3)Excellent
    Winter Springs
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Patio
    • Washer
    • Porch
    • DVD Player
    • Air Conditioning
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2015
    We loved our stay at Bird Nest, the house is very comfortable, our girls had a lot of fun in Orlando and we could relax and enjoy every moment during our Holiday vacations...
    See all reviews
    About this property
    7 nights $1,500 14 nights $3,000 High Season is in effect right now. Hi my name is Beth Goldstein, I live in Winter Springs Florida. You can see more pictures and information on FB under Birdnest Retreat Short Term Rental I rent my well loved home out short term as I travel frequently to visit...
    View all property information
    Location Information
    Winter Springs, Florida 32708
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Fern Park
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
    Make Enquiry
    Maitland
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Internet Access
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to...
    View all property information
    Location Information
    Maitland, Florida 34747
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Fern Park
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Parking
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
    Make Enquiry
    Save time - get the best Longwood rentals sent straight to your email!
    Get the List
    Fern Park
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer Book today to enjoy exclusive extras unique to Top Villas Free transfers to...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Lake Mary
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Parking
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have the Sunshine State retreat of a lifetime at this alluring 4-bedroom, 2-bath Lake Mary vacation rental house. Your vacation begins the moment you arrive at the bright residence, surrounded by a vibrant green lawn and verdant tropical plantings that lead you right up to the front door. Boasting...
    View all property information
    Location Information
    Lake Mary, Florida 32746
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Fern Park
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Parking
    • Satellite TV
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    Casselberry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the gated resort community of Storey Lake. A new community in Kissimmee - this will have all you want and more. This gorgeous 4 bedroom and 3 bathroom home sleeps you and 7 guests perfectly. With all the amenities of home, you will feel at ease and ready for vacation. As you enter the...
    View all property information
    Location Information
    Casselberry, Florida 32707
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Maitland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful 3 bedroom, 2 full bathrooms home is located in a lovely and quiet community. Close to shops, restaurants, just minutes away from Winter Park. Great for Disney vacations, corporate housing, holidays, UCF, or just to relax in sunny Florida. While in Florida this is your lovely home to...
    View all property information
    Location Information
    Maitland, Florida 32751
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • Parking
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have the Altamonte Springs trip of a lifetime with this upscale 3-bedroom, 2-bath vacation rental home, which sleeps 6. Offering wonderful amenities such as a swimming pool, screened-in porch, and an ideal central Florida location minutes from popular Orlando attractions, this quaint residence has...
    View all property information
    Location Information
    Altamonte Springs, Central Florida 32714
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Maitland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Washer
    • DVD Player
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Close to everything. Minutes off major highway I-4. 2 bedrooms, 2 baths. Large living area, fully stocked kitchen, laundry, dinning room, great private porch & pool area. Plus outdoor shower. 30-40 minutes to attractions. 60 minutes to the beaches.<BR>Our guests call our home a fun & relaxing...
    View all property information
    Location Information
    Maitland, Florida 32751
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Fern Park
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview This 6 bedroom home, located at the Encore Club, is only about a 10 minute drive to Walt Disney World and their 4 amazing theme parks where you and your family can create magical memories that last a lifetime! The Encore Club also offers on property amenties such as a waterpark and...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Condo/Apartment - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Make Enquiry
    Fern Park
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview This 6 bedroom villa is the perfect option for families wanting a memorable vacation in one of Orlando's prime location! The Encore Club is situated about 10 minutes from Walt Disney World and offers on site amenities such as a fabulous clubhouse with a bar and restuarant as well as an...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Condo/Apartment - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Make Enquiry
    Fern Park
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview This 8 bedroom rental home is located at the Encore Club, less than 10 minutes to Walt Disney World and their 4 incredible theme parks! Enjoy exclusive amenities right on property, such as a water park featuring thrilling drop and twisting slides, a children’s water playground, an adult...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Condo/Apartment - 8 Bedrooms, 7 Bathrooms, Sleeps 16
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Fern Park
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Parking
    • Satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to...
    View all property information
    Location Information
    Fern Park, Florida
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Fern Park
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview This 8 bedroom villa is located at the Encore Club, situated less than 10 minutes to Walt Disney World, and offers exclusive amenities right on property including a waterpark and clubhouse with a fitness center as well as a bar and restaurant! Sleeping up to 16 people, EC180 has bedrooms...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Condo/Apartment - 8 Bedrooms, 7 Bathrooms, Sleeps 16
    Make Enquiry
    Fern Park
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview This modern 6 bedroom villa, located at the Encore Club, is just about a 10 minute drive to Walt Disney World and their 4 incredible theme parks! You and your family can create magical memories together only down the road from your vacation home! The Encore Club also offers exclusive on...
    View all property information
    Location Information
    Fern Park, Florida 34747
    Condo/Apartment - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Make Enquiry
    Springs Plaza
    4 Bedrooms, 3 Bathrooms, Sleeps 50 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the Regal Palms resort in Davenport this is a pretty end of terrace 2 storey town home with 4 bedrooms and 3 5 bathrooms The downstairs has been newly tiled and the whole villa is tastefully decorated and furnished As you enter there is a master bedroom with queen bed double closet...
    View all property information
    Location Information
    Springs Plaza, Florida 33897
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 50
    Make Enquiry
    Maitland
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An unforgettable Florida adventure awaits your arrival at this 3-bedroom, 2.5-bath Maitland bungalow! This spacious home sleeps 6, is situated on a spacious quarter acre of land, and is close to Orlando, Winter Park, and the unique shops and restaurants of Park Avenue. You and your crew will soak...
    View all property information
    Location Information
    Maitland, Florida 32751
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Fern Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Parking
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Start your Florida vacation out right at this 1-bedroom, 1-bathroom Fern Park vacation rental home. Enjoy the sparkling swimming pool, prime location, gas grill, wireless internet access, cable TV, screened porch, in-unit laundry machines, and more! Perfect for small families, couples, and close...
    View all property information
    Location Information
    Fern Park, Florida 32730
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property
    Owner log in