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.

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An outdoor seating area features blue Adirondack chairs and a patterned table, arranged on a concrete patio. Two large trees provide shade, and a swing is visible in the background. The space is accented with decorative rugs and greenery, fostering a relaxed atmosphere.
Home in Sanford
4.92 out of 5 average rating, 264 reviews

Farmhouse-Chic Retreat with a Charming Patio

Guests have full use of the house, including a spacious kitchen. Four bedrooms with memory foam mattresses ensure you can sleep comfortably. The dining room table can seat 6-8. In the living room there’s a comfortable seating area across the room from a large desk - great for those traveling for work! There is a separate laundry room off the back patio. Guests will have complimentary use of detergent. Iron and ironing board are also available for guest use. On the property there’s an occupied mother-in-law apartment - with separate parking and it’s own entrance so that guests staying in the house are not disturbed by the apartment’s full-time occupant. The backyard is also has a dividing fence for house guests’ privacy. As a guest staying at the house you will have privacy, but I’m local nearby and can assist guests at their request. Behind the house is an occupied apartment that has its own entrance, parking, and backyard. Nestled into a cluster of moss-draped oaks, the house is only a short drive from restaurants and shops in Lake Mary and quaint downtown Sanford. The best way to navigate the area is by car. There are several car rental agencies nearby, with the Orlando-Sanford International Airport just 5-7 min drive.

Guest favorite
Two red kayaks are positioned on a tree trunk beside a peaceful lake, reflecting blue skies and lush greenery. A covered patio area is visible, alongside a hot tub, creating an inviting space for relaxation by the water.
Home in Lake Mary
4.85 out of 5 average rating, 363 reviews

Independent Unique Lake guest house/kayaks/jacuzzy

Independent Guest house with a beautiful lake where you can have unlimited kayaking use during your stay as option(2 kayaks). Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl, walking distance to windixie super market, downtown Lake Mary, dunking donuts , near Orlando Sanford International Airport. Walk to many restaurants and entertainment, 30 min to Daytona Beach. Near Wekiva springs. To go to Disney or Universal, we have easy access to I-4 and 4-17.

Top guest favorite
A screened wrap-around porch offers views of the lake, with sunlight casting striped shadows on the floor. Two lounge chairs are positioned for relaxation, while a colorful playpen is set against the railing. Decorative surfboards are mounted on the walls, enhancing the space's charm.
Cottage in Sanford
4.98 out of 5 average rating, 251 reviews

Lakefront,Sanford airport, Boombah, Venue 1902,UCF

The lake front cottage is located on a private estate 1 mile south of Sanford airport, 4 miles to Sanford historic district, and 3 miles from Boombha Sports Complex. This cottage has a Fully equipped kitchen, light bright liv/din area, screened wrap around porch. Perfect spot for your next family vacation or weekend get away. While staying at the cottage you are welcome to enjoy our paddle boards and kayaks. Also catch and release fishing. No pets. Discounts for non-refundable cancellations.

Top guest favorite
The exterior of the home features a welcoming front entrance with a gray door and arched window. The pathway is lined with colorful foliage, and tropical plants surround the entrance. A lamp post stands at the forefront, providing soft illumination amidst the lush greenery.
Home in Sanford
4.98 out of 5 average rating, 283 reviews

Clean, cozy home in a GREAT location

This clean, comfortable home is in a peaceful neighborhood and centrally located to everything you may wish to enjoy while on your Central Florida vacation. Literally two to three minutes away from I-4, highway 417 and a multitude of shopping and dining options. Universal Studios, Sea World and Daytona International Speedway are all within about 40 minutes, while Disney World and Kennedy Space Center are about 50 - 60 minutes. Also easy access to Sanford and Orlando International Airports.

Top guest favorite
A comfortable sitting area is visible, featuring a blue sofa with yellow accent pillows, a gray armchair, and a dark wood TV stand with a large flat-screen TV. Natural light filters through the large windows adorned with blinds, creating a bright and inviting space.
Guest suite in Altamonte Springs
4.98 out of 5 average rating, 125 reviews

Private Studio King Bed & Massage Chair + Sofa

Quiet, peaceful & centrally-located private studio in Altamonte Springs. 1st floor, 2 private entrances, full kitchen, private AC, strong WiFi, free parking, and total privacy. Walk to Sandlando Park & Seminole Wekiva Trail. Just 2 blocks from I-4, 1.5 mi to Cranes Roost, Uptown & Altamonte Mall. Less than 10 min to Downtown Orlando, Wekiva Springs, hospitals & shopping. Ideal for remote work, extended stays, couples or solo travelers. Enjoy comfort, location & convenience. Book now and enjoy!

Top guest favorite
A serene pool area features a clear blue pool surrounded by elegant tile flooring. Comfortable lounge chairs are arranged around the pool, providing ample space for relaxation. Potted plants add a touch of greenery to the setting, contributing to a calming atmosphere.
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 389 reviews

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

Top guest favorite
A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.
Guesthouse in Longwood
4.98 out of 5 average rating, 135 reviews

"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.

Top guest favorite
A screened-in pool area features a clear blue pool surrounded by landscaped greenery. A stone waterfall adds a natural touch, complemented by decorative plants and a Zen-inspired statue. Sunlight filters through the trees, enhancing the tranquil ambiance.
Home in Longwood
4.97 out of 5 average rating, 120 reviews

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.

Top guest favorite
The image depicts a calm lake at sunset, with reflections of clouds and colors mirrored in the water. In the foreground, a fishing boat is anchored, positioned near the lake's serene shoreline surrounded by lush greenery.
Home in Longwood
4.95 out of 5 average rating, 165 reviews

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

Top guest favorite
A bright outdoor lounge area is furnished with comfortable wicker sofas, set against a backdrop of large windows overlooking a shared saltwater pool. A colorful area rug adds vibrancy, while a ceiling fan circulates air within the space.
Guest suite in Lake Mary
4.96 out of 5 average rating, 387 reviews

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized jetted tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Guest favorite
A spacious pool area is surrounded by tropical landscaping, featuring tall palm trees and flourishing plants. The pool includes a spa with cascading water features. A bright red umbrella provides shade over a seating area, creating an inviting outdoor space for relaxation.
Home in Lake Mary
4.9 out of 5 average rating, 287 reviews

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

Top guest favorite
A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.
Treehouse in St. Cloud
4.97 out of 5 average rating, 1,126 reviews

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.

Popular amenities for Longwood vacation rentals

When is the best time to visit Longwood?

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Frequently Asked Questions

  • Are there family-friendly house rentals in Longwood?

    Longwood has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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.

  • Are there pet-friendly house rentals in Longwood?

    Four-legged friends are welcome in Longwood. Choose from more than 30 house rentals for guests traveling with pets.

  • 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.

  • 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!

  • Where should I stay in Longwood?

    Make yourself at home in Longwood by choosing from our most frequently booked neighborhoods. We have over 140 vacation rentals in Sanlando Springs, and over 740 vacation rentals in Zellwood.

  • Do house rentals in Longwood have air conditioning?

    Absolutely! We offer over 70 house rentals with air conditioning in Longwood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Longwood have a kitchen?

    Absolutely! We offer over 60 house rentals with a kitchen in Longwood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Longwood have wifi?

    Absolutely! We offer over 70 house rentals with wifi in Longwood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Longwood have free parking?

    Absolutely! We offer over 70 house rentals with free parking in Longwood. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Longwood

  • Total vacation rentals

    Explore 90 vacation rentals in Longwood

  • Nightly prices starting at

    Longwood vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 4,530 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 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

    90 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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