
Vacation rentals in Longwood
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Top-rated vacation rentals in Longwood
Guests agree: these stays are highly rated for location, cleanliness, and more.

Redbird cottage and farm. Equestrian lake cottage
Step back into “Old Florida” charm at this updated 1968 lake cottage, on a 7-acre equestrian farm. Secluded from main roads yet just minutes from downtown Mount Dora and Eustis, this peaceful retreat offers the perfect blend of rustic serenity and comfort. Located on a lake that offers direct water access. Campfires are welcomed, and the tranquil setting is made even more magical by the sight of horses. Inside, you'll find cozy touches and comfortable furnishings, including pillow-top mattresses

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.

Tiny Home Near the Springs
Fresh air and back to nature. Imagine a tiny but comfortable hotel room in a rural setting. You'll hear roosters crow as the sun rises. Take a walk on a moonless cloudless night, and you may see stars. This 190 sq. ft. tiny house is a ten minute drive to either Rock Springs or Wekiva Springs, a four minute bike ride to the West Orange Trail which runs for 22 miles, and a 15 minute drive to the Lake Apopka Wildlife Drive. The major theme parks are a 30 to 45 minute drive, depending on traffic.

St. Augustine suite
Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

"Winnie's Place" A Peaceful Guesthouse with Pool.
Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. 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 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

Nature Unique lake view Tiny Guest studio
Tiny Guest house studio with separate entrance for privacy and amazing Lake view. Unlimited rental of 2 Blue kayaks included during stay!! Walking distace from windixie supermarket, downtown lake Mary, restaurants, shopping centers, entertainment and dunking Donuts. Common areas outside studio are shared. Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl. 30 min to Daytona Beach. Near Wekiva springs. To go to Disney, easy access to I-4 and 4-17.

Relaxing 3-Bedroom Pool Getaway
This is a 3-bedroom 2-bath home, bathroom in the main bedroom connects directly to the pool. Accommodates comfortably up to 6 people. We have a wide range of amenities including wifi, TV, covered pool, fully equipped kitchen, and more! This is located in a quiet neighborhood located 30 minutes from Universal Studios, Sea World, and Disney World. The home comes with pool toys, board games, a space for an outdoor bar! The outdoor space is enclosed to keep out mosquitos and other pests.

Pvt Fishing lk , Pets,Nature, Pool,garage
No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes , peaceful boardwalk / dock. Large extra parking for trailers or work trucks. Fishing gear / poles. 2 car garage for safely storing whatever you bring. Fishing gear, tools, bikes, Harley's. Located near Seminole Trail, parks, sun-rail station. 45-60 min from the beach or the attractions DISNEY, UNIVERSAL STUDIOS, close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

Little Hidden Cottage- Near Sanford Airport
Located in Sanford FL, our Hidden Little Cottage is a private studio guest house with its own entrance, features full kitchen & bath room, queen size bed, full size pull out couch & twin size travel bed, & provides flexible self check-in. We are located 7 minutes from the Sanford Airport and Boombah Sports Complex, 10 minutes to Downtown Sanford, I –4 & 4–17. We’re also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts

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.

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.

The Cypress House
This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb
Popular amenities for Longwood vacation rentals
Other great vacation rentals in Longwood

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Krater Key Lake House

The Longwood Escape • Orlando Access
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$30,681 GYD | G$25,464 GYD | G$31,099 GYD | G$26,090 GYD | G$27,342 GYD | G$25,881 GYD | G$25,881 GYD | G$31,725 GYD | G$28,386 GYD | G$26,716 GYD | G$32,769 GYD | G$32,143 GYD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
Are there family-friendly house rentals in Longwood?
Longwood has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Longwood have free parking?
Absolutely! We offer over 60 house rentals with free parking in Longwood. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Longwood?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with wifi, over 60 homes with free parking, over 60 homes with air conditioning, over 50 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there house rentals with a dedicated workspace in Longwood?
Yes! Work meets play with ease at over 30 house rentals in Longwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Longwood have wifi?
Absolutely! We offer over 60 house rentals with wifi in Longwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Longwood have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Longwood. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Longwood?
Make yourself at home in Longwood by choosing from our most frequently booked neighborhoods. We have over 130 vacation rentals in Sanlando Springs, and over 680 vacation rentals in Zellwood.
How much does it cost to stay in house rentals in Longwood?
Experience the best of Longwood with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Longwood have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Longwood. Enjoy a tailored experience with all the comforts you desire.
Are there Longwood house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Longwood, available on Airbnb. Make a splash and soak up the sun in style!
Quick stats about vacation rentals in Longwood

Total vacation rentals
Explore 80 vacation rentals in Longwood

Nightly prices starting at
Longwood vacation rentals start at G$6,262 GYD per night before taxes and fees

Verified guest reviews
Over 3,950 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Longwood vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Longwood rentals

4.8 Average rating
Longwood stays are highly rated by guests—averaging 4.8 out of 5!
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