Family-friendly vacation rentals in Longwood

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Longwood

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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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
4.86 out of 5 average rating, 337 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.

Guest favorite
A spacious living room is featured with light-colored tile flooring. A large flat-screen television is mounted on the wall above a dark media console. One side includes a sleek sofa and a foldable futon, while a round coffee table is situated in the center.
Guest suite in Altamonte Springs
4.94 out of 5 average rating, 185 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

Enjoy a stylish experience with *remodelled pool* in this Altamonte Springs Florida guest suite. This luxury 830 sq ft unit offers a living room, kitchenette, bedroom, bathroom and large pool in the peaceful Spring Valley Farms residential community. It is located 8 miles north of downtown Orlando, a primo location close to downtown, both ocean coasts, Wakiwa Springs State Park, theme parks (Disney, Universal, SeaWorld, more), Crane's Roost, and many other great destinations in central Florida!

Guest favorite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.88 out of 5 average rating, 588 reviews

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.

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
4.97 out of 5 average rating, 107 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!

Guest favorite
A compact space features a trundle bed topped with a floral comforter and decorative pillows. Framed artwork adorns the wall above, while a small dining table for two is positioned nearby. A kitchenette with a microwave and refrigerator is visible, with natural light streaming through the window.
Tiny home in Apopka
4.97 out of 5 average rating, 232 reviews

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.

Top guest favorite
A spacious outdoor area features a pool surrounded by a tiled patio. Comfortable lounge chairs are neatly arranged around the pool, while decorative planters with blooming flowers add a touch of color. The setting is complemented by manicured lawns and a clear sky.
Apartment in Altamonte Springs
4.96 out of 5 average rating, 333 reviews

St.John suite

Luxurious space with PRIVATE ENTRANCE, 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 lined streets, 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, 120 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, 102 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.

Guest favorite
Guesthouse in Sanford
4.95 out of 5 average rating, 173 reviews

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

Guest favorite
A modern kitchen features white cabinets and stainless steel appliances, complemented by granite countertops. A large island with seating is positioned centrally, while the dining area is visible through glass doors leading to the backyard.
Home in Longwood
4.93 out of 5 average rating, 236 reviews

Cozy 3 Bedroom Home, Great location!!

Equipped with one camera near the keypad facing the front door and is recording 24/7 , and perfectly situated in an ideal location. The marble countertops and stainless steel appliances create a dreamlike setting. The fenced backyard features a barbecue grill, smart TVs, and board games. Note: we charge an event fee; do not book without discussing and paying the fee. Minutes from I-4, Wekiwa Springs State Park, Disney, and Downtown Orlando. Book this exquisite sanctuary today.

Guest favorite
A spacious studio features a large bed adorned with a patterned quilt, flanked by two bedside lamps. Dark wooden shelves and a small kitchenette are visible, while warm wooden flooring complements the inviting interior. Natural light fills the room through a nearby door.
Guest suite in Lake Mary
4.95 out of 5 average rating, 126 reviews

Quiet, Upscale Studio

Private, quiet, beautiful studio hidden in plain sight. This is a great alternative to a room at a four star hotel for a fraction of the cost. Perfect for the business traveler, consultant, couple or just for a peaceful getaway for you or you and a friend. Close to shopping, restaurants, sports facilities, multiple downtown areas within 5 to 15 minutes in any direction. This spacious studio boasts a comfortable, serene space for your time away from home!

Guest favorite
A cozy bedroom features a black platform bed dressed in a navy and white patterned duvet. A wooden dresser stands adjacent to the bed, and a small desk is positioned nearby. Natural light illuminates the space, highlighting the serene beach artwork on the wall.
Guest suite in Eatonville
4.97 out of 5 average rating, 191 reviews

Private entrance/bathroom 10 min from DT Orlando

Welcome to your home away from home! Our cozy room with a attached bathroom is the perfect retreat for your visit to Orlando. Located just 10min from downtown Orlando, 30min from MCO and Disney, and 20 min from Universal, you'll have the best of both worlds - convenience and comfort. Whether you're here for business or pleasure, our room is the perfect place to call your temporary home. Book your stay with us today and experience the best of our city.

Popular amenities for Longwood family-friendly rentals

When is the best time to visit Longwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$41,842 GYDG$40,796 GYDG$41,633 GYDG$38,704 GYDG$36,612 GYDG$41,633 GYDG$41,842 GYDG$40,796 GYDG$40,378 GYDG$38,286 GYDG$40,796 GYDG$41,424 GYD
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Quick stats about vacation rentals that are family-friendly in Longwood

  • Total vacation rentals

    Explore 50 vacation rentals in Longwood

  • Nightly prices starting at

    Longwood vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,320 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 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!