
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.

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.

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**

"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

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!

Gated community XL pool Home 2500sq/f
Our LK Mary home sits in Between the 2 most famous places central Florida has to offer, Disney World & Daytona beach and everything else in between. This property sits on 1/2acre of land, tropical landscaped backyard making your stay with us the true Floridian experience . Total privacy with quite nights for a full rest. NO BIKERS PLease! My home is in a Gated community.1 mile to Dtwn Lake Mary. Our pool is NOT heated, the hot tub only CAN be headed at an additional cost

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

Private 4-Bedroom home with pool!
Entire home located on 1 acre of land in the luxury neighbor hood of Markham Woods. This property is the ideal place to stay for a family vacation, or business trip. Take a swim in our large pool and enjoy the Florida Sun! Please add exact number of your guests, in your booking! Please NO Parties or gatherings! Please NO smoking on the property. If any violation occurs, your stay will be terminated immediately, and you will be charged a $1,500 fine!
Popular amenities for Longwood vacation rentals
Other great vacation rentals in Longwood

Lakefront,Sanford airport, Boombah, Venue 1902,UCF

“Lakefront” Guesthouse Getaway

“The Shed" in Historic Downtown Sanford

Nob Hill-Comfort cozy home away from home Longwood

Lake Mary Guest House

Private entrance/bathroom 10 min from DT Orlando

Peaceful Longwood Home – Minutes to Attractions 4B

New Mid Century-Modern Studio
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 126 | € 104 | € 127 | € 107 | € 112 | € 106 | € 106 | € 130 | € 116 | € 109 | € 134 | € 132 |
| 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 air conditioning, over 50 homes with a kitchen, over 60 homes with free parking, over 60 homes with wifi, 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 680 vacation rentals in Longwood, and over 130 vacation rentals in Sanlando Springs.
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 € 26 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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