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Family-friendly vacation rentals in Winter Park

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Winter Park

  • Total vacation rentals

    Explore 190 vacation rentals in Winter Park

  • Verified guest reviews

    Over 9,970 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    180 of Winter Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Park rentals

  • 4.9 Average rating

    Winter Park stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art

Top-rated family-friendly rentals in Winter Park

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

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Guest favorite
A spacious living area features a large, deep-seated sectional couch adorned with decorative pillows. A wooden tray rests on the couch. A dining table with chairs is positioned near bright windows, enhancing the natural lighting in the room.
Home in Winter Park

Stylish newly updated home in Winter Park

Sleeps 8 people comfortably but can fit 10. This home has VERY CONVENIENT ACCESS TO I-4 making it easy to get to Orlando's most sought after attractions, including Park Avenue, Downtown Orlando, Rollins College, Leu Gardens, Mills Ave, Baldwin Park, College Park, Camping World Stadium, Amway Arena, SunRail, and many hospitals. SHORT WALK to 3 notable restaurants Also nearby: Universal Studios (20 min) Outlet Mall (20 min) International Drive (25 min) Orlando Airport (30 min) Disney (~30-40 min)

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 205 reviews
Top guest favorite
A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.
Home in Orlando

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

Indoor spacesKitchenAmenities

4.96 out of 5 average rating, 172 reviews
Top guest favorite
A comfortable living area features a warm orange sofa paired with a matching accent chair. A round coffee table sits on a colorful area rug. Large windows provide ample natural light, and artwork adorns the walls. A dining space is visible in the background.
Guesthouse in Orlando

King/Queen Quiet Vibey Bungalow Guest House

Our beautifully renovated 1950's home is nestled in a quiet neighborhood just a few blocks from everything. The ColonialTown North district of Orlando (also called Mills/50) is a vibrant, central area with exceptional walkability to grocery stores, a trendy bar scene, LOTS of coffee and boba options, foodie restaurants and casual late night eats. Families will love the playground just two streets away. When you're ready, retreat to our front deck and watch the sunset reflect off the trees!

FamilyKitchenAccuracy

5.0 out of 5 average rating, 114 reviews
Top guest favorite
A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.
Guest suite in College Park

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, zip code 32804. 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 add the pet to the reservation.

KitchenIndoor spacesSleep quality

4.97 out of 5 average rating, 335 reviews
Top guest favorite
The exterior of the two-story cottage is captured, showcasing a red and white color scheme with black shutters. Lush green landscaping and a well-maintained lawn surround the home, while a concrete driveway leads to a detached garage nearby. A white picket fence adds charm to the property.
Guesthouse in College Park

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

Indoor spacesFamilyParking

4.91 out of 5 average rating, 198 reviews
Guest favorite
A comfortable living area features a large sectional sofa, complemented by cushions in various patterns. A stylish geometric wall decor piece is visible, along with a sleek television mounted on the wall, emitting soft ambient lighting. Wood flooring adds warmth to the space.
Bungalow in Winter Park

Cozy 2/2 Home - Downtown Winterpark/Orlando

You will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, 5 minutes from Advent Health Hospital, you will be 5 minutes from Downtown Orlando an, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! Dubsdread golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music

Indoor spacesFamilyLong stay

4.97 out of 5 average rating, 352 reviews
Top guest favorite
A stylish kitchen is equipped with modern stainless steel appliances, including a refrigerator and microwave. A central island features two metallic stools, and the cabinetry is finished in a soft gray. A small potted plant adds a touch of greenery to the space.
Guesthouse in Orlando

Location, Location, Location!

Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 min)

Indoor spacesKitchenCheck-in

4.99 out of 5 average rating, 135 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!

Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

Indoor spacesKitchenCheck-in

4.98 out of 5 average rating, 130 reviews
Guest favorite
A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.
Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

KitchenFamilyLocation

4.83 out of 5 average rating, 127 reviews
Top guest favorite
A serene bedroom features a spacious bed dressed in crisp white linens, flanked by modern bedside lamps. A vibrant floral accent wall adds a pop of color, while light filters through plantation shutters, creating a calming atmosphere.
Home in College Park

1927 Bungalow · Walk to College Park Shops

A 1927 bungalow in College Park with its original character intact — plantation shutters, wood floors, a record player and a wall of albums worth digging through. A walk-everywhere address: Publix, Starbucks and the shops on Edgewater are two minutes away. Inside, a full kitchen with dishwasher, in-unit laundry, 1000 Mbps fiber and a real desk with ethernet — a week here works as easily as a weekend. Private patio and driveway parking for two.

Indoor spacesFamilyQuiet

4.97 out of 5 average rating, 118 reviews
Guest favorite
Home in Orlando

Last Minute Deals End Soon, Orlando Home Pool Dock

Newly remodeled 4/2 waterfront home with private pool and relaxing dock, single family house located in East Orlando Florida, close to Siemens, Lockheed Martin, the University of Central Florida (UCF), Rollins College, Full Sail University, Valencia Community College, Winter Park, Central Florida Research Park and Quadrangle and major attractions Walt Disney World and Universal Studios, highways and beaches.

FamilyIndoor spacesCondition

4.97 out of 5 average rating, 120 reviews
Top guest favorite
Guesthouse in Maitland

Chez Bienvenu

Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space

KitchenFamilyBathroom

4.88 out of 5 average rating, 444 reviews

Popular amenities for Winter Park family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

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

KitchenIndoor spacesNearby

4.99 out of 5 average rating, 209 reviews
Guest favorite
An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.
Home in Orlando

Stunning Orlando Getaway w/Spa & Heated Pool

Indoor spacesKitchenLong stay

4.92 out of 5 average rating, 178 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

FamilyKitchenBackyard

4.93 out of 5 average rating, 137 reviews
Top guest favorite
A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.
Guesthouse in Orlando

1924 Spanish Carriage House Lower

KitchenIndoor spacesBackyard

4.98 out of 5 average rating, 151 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

KitchenIndoor spacesDecor

4.97 out of 5 average rating, 132 reviews
Superhost
Home in Maitland

The Bird House Spa Winter Park

KitchenIndoor spacesBathroom

4.91 out of 5 average rating, 104 reviews
Top guest favorite
A quaint exterior view of a small house surrounded by lush greenery. The porch is framed by a railing and features a couple of chairs, while string lights add a charming touch. Colorful flowers bloom in the foreground, enhancing the serene atmosphere.
Guesthouse in Orlando

Garden House near Orlando's cultural hub

Indoor spacesFamilyCheck-in

4.95 out of 5 average rating, 473 reviews
Guest favorite
The exterior of a modern shipping container suite is displayed, featuring large windows that allow natural light to flood the interior. The surrounding landscape includes gravel and low-maintenance foliage, with a small deck leading to the entrance, emphasizing the blend of nature and contemporary design.
Tiny home in College Park

Luxury Shipping Container-HotTub- 30 min to Disney

Indoor spacesKitchenCondition

4.92 out of 5 average rating, 198 reviews

Family- and pet-friendly home rentals

Guest favorite
A living area is presented with a gray sectional sofa and a blue accent chair. The space is enhanced by a patterned area rug and a small coffee table made of wood. Light filters through window blinds, illuminating the room's cozy decor and shelves filled with books.
Home in Orlando

The Sunrise House

Indoor spacesFamilyCheckout

4.84 out of 5 average rating, 122 reviews
Top guest favorite
A serene pool area is featured, reflecting the clear blue sky and surrounding greenery. The pool is bordered by a tiled edge, with colorful plant life adding vibrancy. A covered patio with a picnic table sits in the background, offering a shaded relaxation area.
Home in Orlando

Modern Tropical House Heated Salt Pool

FamilyKitchenCheckout

4.92 out of 5 average rating, 180 reviews
Top guest favorite
A cozy bedroom showcases a queen bed with an orange floral duvet cover and matching pillows. Three pieces of wall art in soft hues are displayed above the headboard. A door leading to the private entrance is visible, providing easy access.
Apartment in College Park

College Park/Winter Pk 1 bed/bath private entrance

KitchenFamilyCondition

4.92 out of 5 average rating, 374 reviews
Top guest favorite
A private pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant greenery. The sparkling blue water of the pool reflects the sky, while a paved pathway leads to the entrance. A serene atmosphere is created by the nearby plants and outdoor decor.
Home in Maitland

Orlando area pool home in Maitland

KitchenIndoor spacesWalkability

4.95 out of 5 average rating, 187 reviews
Top guest favorite
A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.
Home in Orlando

Private pool home near Downtown

KitchenIndoor spacesAir conditioning

4.96 out of 5 average rating, 184 reviews
Top guest favorite
This spacious backyard features a uniquely-shaped pool surrounded by loungers and umbrellas, perfect for soaking up the sun. Lush greenery and palm trees provide a tropical retreat, while soft evening lighting adds to the serene atmosphere, making it an inviting spot for relaxation.
Home in Orlando

Private Pool Oasis w/Xbox, Fireplace, Projector

Indoor spacesFamilyParking

4.95 out of 5 average rating, 110 reviews
Top guest favorite
Townhouse in Orlando

COMFY 2BR/2BA Escape — Pets Welcome FREE!

Indoor spacesKitchenTV

4.93 out of 5 average rating, 273 reviews
Guest favorite
A tranquil backyard features a sparkling pool surrounded by lush greenery and palm trees. Sunlight reflects off the water, creating a serene atmosphere. A covered seating area adds to the comfort, enhancing the outdoor space that overlooks a picturesque view of Lake Gandy.
Home in Orlando

Recharging Lakeview Oasis w/Pool centrally located

KitchenIndoor spacesDecor

4.88 out of 5 average rating, 110 reviews

Family-friendly home rentals with a pool

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

KitchenIndoor spacesCheck-in

4.95 out of 5 average rating, 112 reviews
Top guest favorite
The exterior of the Cozy Cottage is designed with a welcoming green facade, featuring glass doors that open to a charming patio. A stone path leads to a small round table with chairs, complemented by a decorative fountain and lush greenery surrounding the area.
Bungalow in College Park

Cozy Cottage in College Park.

Indoor spacesFamilyOutdoor spaces

4.96 out of 5 average rating, 176 reviews
Top 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

Maitland-Orlando Area, FL. Pool House Bungalow

FamilyIndoor spacesGrill

4.88 out of 5 average rating, 631 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

Indoor spacesKitchenAir conditioning

4.86 out of 5 average rating, 139 reviews
Top guest favorite
A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.
Condo in Orlando

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

KitchenFamilyAccess

4.95 out of 5 average rating, 190 reviews
Guest favorite
A bright pink inflatable flamingo floats on the surface of a clear pool, surrounded by tropical plants and a screened enclosure. Sunlight reflects off the water, creating a relaxing atmosphere for outdoor leisure.
Home in Oviedo

4 bedroom Modern pool home, close to UCF&Boombah

Indoor spacesKitchenBathroom

4.92 out of 5 average rating, 381 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

KitchenIndoor spacesHospitality

4.95 out of 5 average rating, 149 reviews
Top guest favorite
A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.
Guesthouse in Orlando

Livingston Pool House- In The Heart of Downtown

Indoor spacesKitchenSolo travel

4.99 out of 5 average rating, 293 reviews

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 588ﺩ.ﺇ 613ﺩ.ﺇ 588ﺩ.ﺇ 558ﺩ.ﺇ 584ﺩ.ﺇ 540ﺩ.ﺇ 514ﺩ.ﺇ 514ﺩ.ﺇ 496ﺩ.ﺇ 540ﺩ.ﺇ 595ﺩ.ﺇ 621
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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