
Family-friendly holiday 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.

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!

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.

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!

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.

"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.

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

Orlando, spacious, quiet, centrally located, suite
This suite includes private entrance, living room, kitchen with utensils and cookware, one bedroom with king bed and private bath. Third and fourth persons may be accommodated with recliner that lays flat into a queen-size bed in living room. Also a queen size air mattress and portacrib is available. Excellent location for Disney, Universal, SeaWorld, and beaches. Approx. 35 min. to Disney; 27 min. to Universal; 23 min. to convention center; 45 min. to beach; and 35 min. to Airport.

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.
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!

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
Family-friendly home rentals with a hot tub

No Airbnb fee! Home Pvt Pool/ Spa/Game Room 244301

Bonheur Ala Maison

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool

Lake View - 5 Miles to Disney!

Themed Home + Near Disney + Arcade + King Bed + Water Park + Spa

1924 Spanish Carriage House Lower

Spacious Home with Pool & Hot Tub near Downtown

3BD/3BA Themed House Near Disney
Family- and pet-friendly home rentals

Lovely Winter Park Home close to Hospitals !

Mirror House

RemodeledHouse w/king beds near Downtown Lake Mary

Guest House near attractions

8th Green Cottage - A relaxing oasis in the city

Quiet Place, convenient to everything!

Cozy Boho Studio in Downtown Sanford

Elegant, Spacious Three Bedroom Residential House.
Family-friendly home rentals with a pool

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

The Cypress House

5 stars! waterpark! GameRm! Ariel Buzz StarWars

2-bedroom home with pool near Kings Landings!

Private Pool at Flamingo Cottage

Lake Front Suite -Close to all Attractions

Tropical Oasis - Heated Luxury Pool - Game Room

Cozy Cottage in College Park.
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $260 SGD | $253 SGD | $258 SGD | $240 SGD | $227 SGD | $258 SGD | $260 SGD | $253 SGD | $251 SGD | $238 SGD | $253 SGD | $257 SGD |
| 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 |
Quick stats about holiday rentals that are family-friendly in Longwood

Total holiday rentals
Explore 50 holiday rentals in Longwood

Nightly prices starting at
Longwood holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 2,320 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Longwood holiday rentals include wifi 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!
Destinations to explore
- Seminole Holiday rentals
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- Rentals with pools Longwood
- Rentals with a washing machine and dryer Longwood
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- Pet-friendly rentals Longwood
- Family-friendly rentals Seminole County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Walt Disney World Resort Golf
- Reunion Resort Golf Courses - Palmer & Watson
- Daytona International Speedway
- Playalinda Beach
- Discovery Cove
- Aquatica
- Apollo Beach
- Island H2O Water Park
- Titusville Beach
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club




