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Family-friendly vacation rentals in Longwood

Find and book unique family-friendly homes on Airbnb

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 2,410 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 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!

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
The inviting pool area is framed by a wooden deck, featuring two lounge chairs and a large umbrella for shade. The clear water reflects the blue sky and surrounding greenery, creating a serene atmosphere for relaxation.
Home in Altamonte Springs

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!😊

Indoor spacesKitchenLocation

4.95 out of 5 average rating, 112 reviews
Top guest favorite
The pool area is enclosed with a protective screen, featuring a spacious heated pool surrounded by a wooden deck. A green umbrella provides shade over a small table and chairs, while a bright yellow building is visible in the background.
Home in Altamonte Springs

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

KitchenFamilyBathroom

4.98 out of 5 average rating, 117 reviews
Top guest favorite
A spacious living area is highlighted by exposed wooden beams above. A light-colored sofa is complemented by two bright orange chairs. A round coffee table is centered on a textured rug, while large windows provide natural light and views of the outdoors.
Home in Altamonte Springs

A Home Where Eclectic Luxury Meets Affordability

Welcome to The Altamonte House. Your home away from home. We offer free amenities, luxury bedding and pillows, and quintessential design throughout the home. There are work spaces in every bedroom, ultra-fast wifi, games galore, and a beautiful outdoor space equipped with outdoor dining and lounging. Events are allowed with fee. Pet Fee's per pet: $100 (notify host if you are bringing a pet-charged separately upon check in) Read the rules of the property before booking, to ensure that you agree.

KitchenFamilyAccess

4.98 out of 5 average rating, 364 reviews
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

Gated community XL pool Home 2500sq/f

Need one night stay , reach out 4 special pricing. home rest between 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 quiet nights for a full rest. ! My home is in a Gated community.1 mile to Dtwn Lake Mary. POOL NOT heated, the hot tub only CAN be headed at an additional cost. NO TRAILERS!!!

FamilyIndoor spacesDecor

4.9 out of 5 average rating, 298 reviews
Top guest favorite
The exterior of a three-bedroom home displays a welcoming entrance with a paved walkway leading to a covered porch. Lush greenery and flowering plants line the front yard, complemented by a white railing. The structure is topped with a metal roof and features large windows.
Farm stay in Apopka

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

Indoor spacesKitchenGetting around

4.95 out of 5 average rating, 149 reviews
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

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.

Indoor spacesFamilyBiking

4.98 out of 5 average rating, 142 reviews
Top guest favorite
A charming lakefront cottage is viewed from across the water, showcasing its blue exterior. The porch area includes a deck with seating, and two light-colored lounge chairs are positioned on the grassy lawn, surrounded by lush greenery and trees.
Cottage in Altamonte Springs

Charming Private Lakefront Cottage Retreat

You can fully relax in this adorable lakefront cottage. We're sure you'll enjoy all of the wonderful amenities this peaceful property has to offer. Our incredibly unique cottage is nestled under a large grand oak tree and tucked away behind climbing jasmine vine clad fencing and security gates. Inside, you will find a new remodeled fully stocked kitchen and luxury bathroom. Our cozy cottage has all the comforts of home and more. Reserve your stay today and enjoy this special property.

Indoor spacesFamilyLocation

4.99 out of 5 average rating, 155 reviews
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

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

Indoor spacesKitchenAccuracy

4.95 out of 5 average rating, 175 reviews
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

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.

FamilyIndoor spacesParks

4.97 out of 5 average rating, 132 reviews
Guest favorite
A well-manicured pathway leads to the studio, surrounded by lush greenery and colorful plants. Visible are large windows framed by white curtains, providing a view of the scenic lake. A patio with a red umbrella and a picnic table is accessible for outdoor relaxation.
Guesthouse in Lake Mary

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.

Indoor spacesKitchenParking

4.9 out of 5 average rating, 145 reviews
Superhost
A backyard swimming pool is surrounded by a natural landscape, featuring colorful floaties resting on the water's surface. Comfortable seating is arranged nearby, and palm trees provide a tropical touch to the serene outdoor setting, all under a softly lit evening sky.
Home in Altamonte Springs

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.

FamilyIndoor spacesQuiet

4.86 out of 5 average rating, 139 reviews
Guest favorite
A modern kitchen area is visible, featuring white cabinetry and a dark granite countertop. A large flat-screen TV is mounted above a fireplace, while a geometric design adorns the wall. Stainless steel appliances are included, providing a stylish and functional cooking space.
Home in Altamonte Springs

Renovated Peaceful Luxury Walk to Mall Park Publix

- Luxury 2 Bedroom/1Bath Style Renovated peaceful home with Fireplace, Skylights, 87 inch TV, Chandelier, & Full kitchen - Spacious bathroom - Americans with Disabilities Act (ADA) bars for shower and toilet & Smart mirror - Outdoor Gym with Kids Playground & Dedicated Laundry Room - 1 minute drive to major highway Orlando ( Disney, Universal, Aquatica, Beaches, Downtown ) Approximately 30 minutes away - Plenty of free private parking right in front of the house - Pet friendly

KitchenFamilyCleanliness

4.87 out of 5 average rating, 127 reviews

Popular amenities for Longwood family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

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

Independent Unique Lake guest house/kayaks/jacuzzy

FamilyIndoor spacesAccess

4.85 out of 5 average rating, 372 reviews
Guest favorite
An outdoor area features a pool surrounded by lounge chairs and a sleek design. Soft lighting illuminates the space, creating a cozy ambiance. A sauna is visible, with a comfortable lounge area nearby, and a large screen mounted for entertainment.
Home in Longwood

Recharge @ Timberland Lodge: Pool Hottub Sauna

FamilyIndoor spacesGetting around

4.89 out of 5 average rating, 109 reviews
Guest favorite
A refreshing pool is captured, with sunlight sparkling on the water's surface. The stone-accented summer kitchen with a wooden pergola is visible in the background, along with plants and seating, creating a relaxed outdoor setting.
Home in Casselberry

Villa with Guest House & Pool-Patio

Indoor spacesKitchenView

4.93 out of 5 average rating, 137 reviews
Guest favorite
A spacious living area features a large sectional couch and a stylish coffee table. Natural light filters through the windows, highlighting modern décor. An arcade game stands in the background, and a laundry area is visible to the left, contributing to the home's functionality.
Home in Casselberry

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

FamilyIndoor spacesValue

4.88 out of 5 average rating, 157 reviews
Top guest favorite
A spacious living area is highlighted by a sleek, modern design featuring polished floors. A green couch and two accent chairs are arranged around a wooden coffee table. A dining table with ample seating is situated nearby, complemented by decorative wall art and soft lighting.
Guesthouse in Orlando

Luxe Guest House| Pool, HotTub| UCF, Rollins

KitchenFamilyView

4.99 out of 5 average rating, 209 reviews
Guest favorite
A spacious outdoor area features a large pool with crystal-clear water, accompanied by a hot tub and a soothing water fountain. Surrounding the pool, a stone patio hosts multiple seating areas beneath a pergola, providing a serene setting for relaxation.
Home in Orlando

Unique Spacious Home w/ Pool near Downtown Orlando

FamilyKitchenBackyard

4.96 out of 5 average rating, 110 reviews
Top guest favorite
A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.
Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

FamilyIndoor spacesHospitality

4.96 out of 5 average rating, 116 reviews
Superhost
Home in Maitland

The Bird House Spa Winter Park

FamilyKitchenValue

4.91 out of 5 average rating, 104 reviews

Family- and pet-friendly home rentals

Superhost
A modern living room is presented, featuring a deep blue sectional sofa and a coordinating armchair. A circular glass coffee table sits at the center, complemented by a decorative vase with flowers. Natural light enters through a large window, enriching the neutral tones of the space.
Home in Altamonte Springs

Elegant, Spacious Three Bedroom Residential House.

KitchenIndoor spacesLong stay

4.86 out of 5 average rating, 222 reviews
Superhost
A modern kitchen features sleek cabinetry and a large island with bar seating. Unique patterned ceiling tiles complement the granite countertops. A stainless steel refrigerator and double ovens are visible, highlighting a functional yet stylish cooking space.
Home in Heathrow

Markham Woods 4BR Pool Retreat near Attractions

Indoor spacesKitchenQuiet

4.85 out of 5 average rating, 127 reviews
Guest favorite
A comfortable seating area features a soft blue chaise lounge beside a side table with a lamp. A large mirror leans against the wall, reflecting natural light from a nearby window. Framed artwork adorns the walls, enhancing the space's aesthetic.
Guest suite in Altamonte Springs

Abe and su villa

Indoor spacesFamilyCheck-in

4.86 out of 5 average rating, 114 reviews
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

Cozy King Studio • Massage Chair • Sleeps 4

FamilyKitchenNearby

4.97 out of 5 average rating, 143 reviews
Guest favorite
Home in Apopka

Lakefront Home•screened deck, dock•Long Stays OK

KitchenFamilyOutdoor spaces

5.0 out of 5 average rating, 107 reviews
Guest favorite
A spacious living area features a large sectional sofa facing a wooden entertainment unit with a television. Natural light enters through window treatments, illuminating the room. Two comfortable armchairs are arranged around a circular coffee table, with views of the surrounding park visible through the windows.
Home in Apopka

Wekiva Springs 5br 4 ba, spacious & lovely home

Indoor spacesFamilyGrill

4.93 out of 5 average rating, 217 reviews
Superhost
An indoor swimming pool is showcased within a spacious area, illuminated by sunlight through large windows. The clear water reflects the blue ceiling beams, while natural stone accents line the poolside, creating a relaxed atmosphere. Comfortable lounge chairs are positioned nearby.
Guest suite in Maitland

Guesthouse w/Private Indoor Pool

FamilyKitchenWalkability

4.78 out of 5 average rating, 390 reviews
Top guest favorite
A private dock extends over the tranquil waters at night, illuminated by soft blue lights. Reflections of distant city lights shimmer on the lake's surface, creating a serene atmosphere. The structure features seating areas for relaxation overlooking the water.
Home in Sanford

Alder wood Lake house near SFB Airport Boombah

Indoor spacesKitchenGetting around

4.93 out of 5 average rating, 128 reviews

Family-friendly home rentals with a pool

Top 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

Comfortable Guest Suite-Stylish Altamonte Springs!

FamilyIndoor spacesSleep quality

4.94 out of 5 average rating, 203 reviews
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

Stylish & spa like Getaway - peaceful garden suite

FamilyKitchenView

4.96 out of 5 average rating, 396 reviews
Guest favorite
Home in Sanford

Private Pool at Flamingo Cottage

KitchenIndoor spacesLong stay

4.87 out of 5 average rating, 284 reviews
Superhost
An open-concept living area features a modern kitchen with a central island and stainless steel appliances. A comfortable sectional sofa is paired with wooden armchairs, and a round coffee table sits in the center. Large windows bring natural light into the space, enhancing the clean, neutral decor.
Home in Apopka

2-bedroom home with pool near Kings Landings!

KitchenIndoor spacesParks

4.83 out of 5 average rating, 172 reviews
Top guest favorite
A modern farmhouse is showcased against a bright blue sky, framed by lush greenery and vibrant flower beds. The entrance features large arched windows and a welcoming front door, while palm trees add a tropical touch to the landscape.
Home in Apopka

Rate Discount~ Pool~Private Country Retreat

FamilyKitchenAmenities

4.99 out of 5 average rating, 134 reviews
Guest favorite
A welcoming living area features comfortable seating arrangements around a central ottoman. A large television is placed on a stylish console, with decorative plants and artwork enhancing the space. Natural light streams through windows, contributing to a bright, inviting environment.
Home in Sanford

The Cypress House

KitchenIndoor spacesBathroom

4.97 out of 5 average rating, 183 reviews
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

St. Augustine suite

KitchenIndoor spacesGrill

4.96 out of 5 average rating, 395 reviews
Top guest favorite
The screened-in pool area features a tranquil pool with a soft blue hue, surrounded by white decking. A small table holds a lit lantern beside two lounge chairs, providing a serene space for relaxation under the evening sky.
Home in Maitland

Florida Poolside Paradise a Great Place to Unwind!

Indoor spacesKitchenLayout

4.98 out of 5 average rating, 130 reviews

When is the best time to visit Longwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$38,075 GYDG$40,795 GYDG$39,330 GYDG$38,912 GYDG$37,866 GYDG$33,054 GYDG$41,841 GYDG$40,795 GYDG$40,376 GYDG$35,983 GYDG$41,422 GYDG$41,632 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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