Family-friendly holiday rentals in Winter Park

4.88 out of 5 average rating, 589 reviews

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

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.

4.98 out of 5 average rating, 124 reviews

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.

Whether you're coming to Orlando for adventure at one of the theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

4.94 out of 5 average rating, 260 reviews

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.

Flat in College Park

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $20 pet fee No cleaning fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 1.9

4.83 out of 5 average rating, 109 reviews

A cozy bedroom features a comfortable queen bed with light blue bedding. Nightstands with lamps are positioned on either side. A wooden barn door and an artwork depicting foliage add a touch of warmth to the modern space, complemented by a sleek black floor.

Tiny home in Winter Park

Comfy Tiny Home @WP. Large Private Deck+Queen bed

This memorable place is anything but ordinary. Welcome to our charming TINY house in the heart of Orlando! Nestled in a quiet neighborhood, this cozy retreat offers the perfect blend of comfort, privacy, and convenience. Whether you're here for business or leisure, our centrally located TINY house is an ideal home base for exploring all that Orlando and Winter Park have to offer. ✅️Private Patio ✅️Free Parking ✅️Deck with outdoor seating 🎢10-15 min from Universal ✈️20-22 min to airport

4.9 out of 5 average rating, 178 reviews

The bedroom features a spacious bed dressed in soft blue bedding, complemented by two bedside lamps on wooden tables. Decorative curtains with a water-themed design frame the window, while a subtle area rug adds texture to the room's original terrazzo flooring.

Flat in Winter Park

The Lake House

Welcome to the mid-century Lake House. 370 square feet apartment with a private entrance and original terrazzo floors. Located on a quiet residential street on a small lake, and located within a 5-minute drive to anything you may need! Starbucks and Panera are within walking distance, and dozens of other places to eat. Publix, Walgreens, and Sprouts are just around the corner. A short 10 minute drive to the famous Park Ave, in Downtown Winter Park with shopping and gourmet restaurants.

4.97 out of 5 average rating, 339 reviews

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 College 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

Guest suite in College Park

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.

4.97 out of 5 average rating, 238 reviews

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.

4.99 out of 5 average rating, 140 reviews

Guest house in Orlando

Baldwin Park Guest House

Welcome to Beautiful Baldwin Park, This Brand New Private sanctuary with modern day decorations, amenities and large screen television is the perfect place for a couple or single to experience the beautiful Orlando area. Conveniently located near the Orlando International Airport, Winter Park and downtown area Enjoy your morning coffee on the private patio . This entire property is very clean and well maintained, we look forward to being your host for your next central Florida visit

4.76 out of 5 average rating, 522 reviews

A cozy studio suite is shown with warm wood accents. A small kitchenette is equipped with a microwave and refrigerator. A workspace with a blue desk and two chairs is visible. Bright green plants add a touch of nature, complemented by a vibrant area rug.

Guest house in Orlando

Private Cozy Cottage in heart of Orlando

Come stay at our Cozy quaint suite located in the historic downtown Lake Davis neighborhood with a 5 minute walk to a quiet neighborhood market, 1 mile walk to downtown Orlando with entertainment and the Downtown Farmers Market. Less than 30 minutes to the worlds greatest attractions Disney, Universal Studios, Sea World etc. The beach is a 1 hour drive. One car parking. The room is connected to a family home you’re able to hear guest next door. Not for parties . Please NO pets.

Guest suite in Eatonville

A cozy bedroom features a black platform bed dressed in a navy and white patterned duvet. A wooden dresser stands adjacent to the bed, and a small desk is positioned nearby. Natural light illuminates the space, highlighting the serene beach artwork on the wall.

4.96 out of 5 average rating, 195 reviews

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.

4.97 out of 5 average rating, 198 reviews

The pool area is illuminated at night, showcasing a crystal-clear water pool surrounded by comfortable lounge chairs. Vibrant bougainvillea lines the back wall, adding a pop of color to the tranquil setting. Soft lighting enhances the modern architecture of the adjacent building.

Flat in Winter Park

Just 3 Blocks to Shops/Restaurants on Park Ave!

Modern, clean and unique. Fast internet speed: 263 MBPS download and 21.5 MBPS upload. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz countertops, high-end cabinetry and fixtures, great new furnishings and mattresses, 8' solid core interior doors, high ceilings, spacious open layout with a balcony offering fantastic sunset views and more! If you haven't explored Winter Park's Park Avenue, then you must!

Campervan/Motorhome in Orlando

An efficient layout showcases the interior of the airstream, featuring a modern kitchenette with a sink and seating area. Along one wall, sleek bar stools are positioned in front of a counter. Soft lighting creates a cozy atmosphere, enhancing the vintage charm.

4.91 out of 5 average rating, 150 reviews

Unique and modern airstream near UCF

Our airstream has all the amenities you need. It is located in our one acre property behind our house (very private) the parking is on the side of our house next to our carport and you will go through a gate and follow the path to the airstream. MCO Airport 12 miles Disney parks 25 mil Universal Studios 16 mil beaches 50 mil UCF 2.4 mil Full Sail 2.4 mil Valencia 3.5 mil Dining, Shopping entertainment and much more!

Popular amenities for Winter Park family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 147 reviews

The cozy sleeping area features a spacious bed adorned with luxurious cotton sheets and coordinating pillows. A rattan headboard complements the tropical-themed wallpaper. A small seating area with a brown couch and decorative pillows is visible, adding to the inviting atmosphere.

Home in College Park

The Boho Jungalow - Private | HotTub I Downtown

4.94 out of 5 average rating, 185 reviews

A collage of images showcases the private cottage's inviting interior and outdoor amenities. The cozy bedroom features a spacious bed, the pool area is lined with lounge chairs, and the game room displays a pool table and bar. The kitchen is fully equipped for convenience.

Cottage in Orlando

Mills Cottage

4.87 out of 5 average rating, 133 reviews

A spacious living area features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.

Home in Maitland

Bonheur Ala Maison

Guest house in Lake Cherokee

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.

4.97 out of 5 average rating, 115 reviews

1924 Spanish Carriage House Lower

4.88 out of 5 average rating, 162 reviews

The exterior of a two-story Spanish Mission-style home is depicted in soft twilight. The structure features arched entryways with large windows, surrounded by lush landscaping. A decorative lantern illuminates the front entrance, enhancing the inviting charm of the property.

Home in Lake Cherokee

3,000 Sqft Historic Home With Pool Near Everything

4.97 out of 5 average rating, 130 reviews

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 Lake Formosa

Spacious Home with Pool & Hot Tub near Downtown

4.9 out of 5 average rating, 119 reviews

The exterior of the home is showcased, featuring a well-maintained front yard with green grassy areas and mature trees. A paved driveway leads up to a garage, while a welcoming front entrance is visible. Natural light highlights the attractive landscaping.

Home in Orwin Manor

Cheerful, updated 4 BR 3B w/ large, lush back yard

4.9 out of 5 average rating, 145 reviews

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

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 165 reviews

A welcoming entrance is framed by a vibrant green leaf panel, with a cheerful sunflower decoration displaying the word 'WELCOME.' The surrounding area features a red fence and a light-colored door leading into the home.

Guest suite in Orlando

Grey House near Orlando Universal Parks

Guest house in College Park

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.

4.91 out of 5 average rating, 184 reviews

8th Green Cottage - A relaxing oasis in the city

Home in Colonialtown South

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.

4.97 out of 5 average rating, 157 reviews

Private pool home near Downtown

4.81 out of 5 average rating, 205 reviews

Home in Orlando

The Calm Green One | Cozy Downtown Stay

Guest house in Wadeview Park

A spacious bedroom features a large bed with white bedding and decorative pillows. Two soft bedside lamps illuminate the area, complemented by a cozy armchair and a decorative bench at the foot of the bed. Exposed brick wall accents the room.

4.98 out of 5 average rating, 116 reviews

The Cottage A Pet Friendly Guesthouse

4.96 out of 5 average rating, 133 reviews

A stylish living area features a gray couch with decorative pillows, placed against a backdrop of textured wood paneling. A world map adorns the wall, while a kitchenette with white cabinetry and a red microwave provides convenient amenities. Glass doors allow natural light to fill the space.

Guest suite in Orlando

Thornton Park Loft Studio

Guest suite in College Park

A welcoming living area features a wall-mounted flat screen TV above a console table. Two patterned ottomans provide additional seating. A vibrant potted plant adds greenery, while framed artwork is displayed on the wall nearby. Light streams through the doorway leading to the bedroom.

4.93 out of 5 average rating, 193 reviews

Charming Getaway Near Downtown & Disney

Guest house in College Park

A comfortable living area features a dark leather sofa, a wooden coffee table, and a dining table with chairs. Bright light filters in from the outdoor patio, revealing lush greenery and a seating area beyond the sliding glass doors adorned with a vibrant red umbrella.

4.96 out of 5 average rating, 458 reviews

The Coach House -2 bedroom/3 bath Orlando Getaway!

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 438 reviews

Two sparkling glasses filled with a bright orange beverage are placed by the edge of a non-heated swimming pool. The pool area is surrounded by lush greenery and light stone walls, offering a serene outdoor retreat.

Guest suite in Oviedo

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

Guest suite in Thornton Park

A serene pool area is surrounded by a well-maintained patio with paver stones. Lush greenery and tall palm trees are visible in the background, creating a peaceful atmosphere. A staircase leads to an upper level, enhancing the outdoor space's layout.

4.97 out of 5 average rating, 238 reviews

Orlando Oasis in the heart of Thornton Park

4.94 out of 5 average rating, 144 reviews

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.

Apartment in Orlando

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

4.92 out of 5 average rating, 365 reviews

A bright dining area with a large table set for meals overlooks a modern kitchen with amenities, including stainless steel appliances. A cozy bedroom features a bed adorned with black and red accents. An aerial view displays a vibrant resort pool area with water slides and lounging spaces.

Townhouse in Kissimmee

Waterpark, Mini Golf, Batting Cage | Near Disney!

Guest suite in Altamonte Springs

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.

4.94 out of 5 average rating, 187 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

4.98 out of 5 average rating, 121 reviews

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.

Guest house in Longwood

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

4.89 out of 5 average rating, 157 reviews

An outdoor pool is centered within a landscaped patio area, surrounded by lush greenery and mature plants. Two teak lounge chairs are positioned in the foreground, facing the calm water, while sun umbrellas and vibrant seating are visible nearby.

Guest house in Orlando

Vintage Florida Vibes House