
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.

Mirror House
Soon as you enter our doors, you'll be enchanted by the blend of modern design with a homely atmosphere. It’s a single-room marvel that offers a comforting sanctuary. Immerse yourself in lines, tasteful furnishings, and a subtle color scheme that sets the stage for a stay. Modern amenities are at your fingertips.Sink into top-quality linens as you bask in the comfort of this space. We guarantee that you wake up feeling refreshed and prepared to embark on a brand new day filled with experiences.

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.

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.

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.

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

New Mid Century-Modern Studio
Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

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

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

The Boho Jungalow - Private | HotTub | Downtown

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

The Weathered Inn at Cedar Knoll Flying Ranch

Bonheur Ala Maison

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

Villa with Guest House & Pool-Patio

Spacious Home with Pool & Hot Tub near Downtown
Family- and pet-friendly home rentals

RemodeledHouse w/king beds near Downtown Lake Mary

Private guest suite - Studio Retreat

Guest House near attractions

Tiny House | Airport & Downtown Orlando 15 Min

Elegant, Spacious Three Bedroom Residential House.

Markham Woods 4BR Pool Retreat near Attractions

College Park/Winter Pk 1 bed/bath private entrance

Private Guest House - With Pool
Family-friendly home rentals with a pool

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

Livingston Pool House- In The Heart of Downtown

The Hillside Haven Oasis

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

2-bedroom home with pool near Kings Landings!

Cozy at Flamingo Cottage

Lake Front Suite -Close to all Attractions

Magical Family Fun House Near Disney Luxury Villa
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $277 CAD | $270 CAD | $276 CAD | $256 CAD | $242 CAD | $276 CAD | $277 CAD | $270 CAD | $267 CAD | $253 CAD | $270 CAD | $274 CAD |
| 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 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 $42 CAD 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

Wifi availability
50 of Longwood vacation 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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- Family-friendly rentals Seminole County
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- Family-friendly rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Walt Disney World Resort Golf
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Old Town Kissimmee
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Daytona International Speedway
- Universal's Volcano Bay
- 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




