
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.

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.

Orlando Poolside Oasis
Welcome to the Orlando Poolside Oasis!! This property is located in a quiet suburb of Orlando, with easy access to both theme parks and the beaches. This 3 bedroom 2 bathroom pool home will allow you to vacation in comfort and style. We have recently completed many upgrades to the property, including a newly renovated kitchen and bathrooms. We hope you love this property as much as we do! The home is also very baby friendly (crib upon request, stroller, baby bath,etc)!We can’t wait to host you!😊

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.

Tropical Pool/Spa Home-Disney-Theme Parks-Beaches
Your Tropical Paradise is ready and fully furnished from top to bottom! The Pool area has a hot tub. Near all attractions. Top of the line furnishings. Split plan--Master Bedroom is a king suite, pvt bathroom, 2 seperate bdrms on the other side of house. Heated pool/ hot tub has an small add'l fee Moments from I-4 & 20-25 minutes to Disney, Sea World, Universal, Famous Names discount malls, 35 minutes to Daytona & New Symerna Beach. Cranes Roost Park, Altamonte Uptown/Mall, 5 min

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!

Farmhouse near the Springs
Enjoy the ducks, chickens, and goats. Wake to the neighbor's rooster crowing. Have fresh eggs for breakfast when the chickens and ducks cooperate. This three bedroom home with a pool sleeps six. It is - 6 minutes to a grocery store, - 12 minutes to Rock Springs or Wekiva Springs, - 15 minutes to the Lake Apopka Wildlife Drive and - 30 to 45 minutes to the major theme parks, depending on traffic. - a 4 minute bike ride to the 22 mile long West Orange Trail. NO PARTIES TWO VEHICLES MAXIMUM

"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.

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

Private Pool / Cozy Central Florida Home
Updated four-bedroom home in Altamonte Springs, ready for your stay! Perfect for groups. Plenty of free parking in the driveway and curb side. Only minutes from I-4, which means easy access to your favorite spots in and around Central Florida. Universal Studios, for example, is about 25 minutes away. SeaWorld is 30 and Disney Springs is about 35, depending on traffic. Plenty of sports complexes are nearby. Uptown Altamonte is just around the corner. No parties or events please.

Quiet Place, convenient to everything!
Spacious home in a very quiet residential neighborhood. Perfect home away from home for your special getaway. Vacations, business trips, wedding groups, graduations have all been hosted in the past, and everyone had a great time. There's significant value in having your own quiet place and multiple rooms in a family-friendly setting. DO NOT BOOK MY QUIET PLACE IF YOUR PLAN INCLUDES ANY LARGE GATHERING WHICH MIGHT IMPACT MY HOME OR NEIGHBORHOOD. YOUR RESPECT IS EXPECTED.

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
Popular amenities for Longwood family-friendly rentals
Family-friendly home rentals with a hot tub

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Bonheur Ala Maison

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

Pool + Heated spa Family friendly King suite Oasis

Unique Spacious Home w/ Pool near Downtown Orlando

5BR Mario& Princess Peach•Pool•Theater•Free Resort

Modern 3BR Near Wekiwa Springs & Orlando
Family- and pet-friendly home rentals

Lake Dora Dream-Waterfront/Pool

Cozy Getaway | Game Garage + Fenced Backyard +more

Guest House near attractions

Abe and su villa

Beautiful Mount Dora Charmer with Lake Ola Views

Renovated Peaceful Luxury Walk to Mall Park Publix

Magnificent Lakefront Home•Swim&Relax•Long Stay OK

Retro Arcade | Close to Downtown | Fenced Yard
Family-friendly home rentals with a pool

Maitland-Orlando Area, FL. Pool House Bungalow

3/2 near beaches and theme parks

Livingston Pool House- In The Heart of Downtown

Mario-Themed Home! | Disney 30 Min | Pool + Lake

Central Florida Pool Home

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

1-Acre Family Paradise, Perfect for Large Groups

Wana Chill Spot *Pool *Spa *Bar *Ping Pong *BBQ
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $233 SGD | $250 SGD | $241 SGD | $237 SGD | $224 SGD | $255 SGD | $256 SGD | $250 SGD | $247 SGD | $220 SGD | $253 SGD | $255 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 60 holiday rentals in Longwood

Nightly prices starting at
Longwood holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 2,480 verified reviews to help you choose

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 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!
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- Pet-friendly rentals Longwood
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- Family-friendly rentals Seminole County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Ocean Center
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Daytona International Speedway
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Playalinda Beach
- Island H2O Live!





