Family-friendly holiday rentals in Pine Hills

4.99 out of 5 average rating, 158 reviews

College Park Villa Oasis w/ Botanical Courtyard

TOP 1% ABNB PRIVATE-SAFE-QUIET Villa Oasis central to DT ORL/Eola/Winter Park. Tranquil bamboo lined Cottage provides relaxed setting in much desired COLLEGE PARK neighborhood. Former recording studio @ 2X the living space of most College Park listings. Newly renovated bathroom, kitchen, outdoor space. Guest's own separate residence, bath/laundry room, garden patio and parking. I-4 EZ access to downtown ORL, Winter Park, THEME PARKS, central Fla activities! PLEASE MESSAGE with ANY QUESTIONS!!!

5 out of 5 average rating, 121 reviews

An exterior view of the guesthouse displays a quaint two-story structure with a black garage and a welcoming front porch. Surrounding greenery provides a natural setting, enhancing the privacy of the location. The two upper windows are adorned with large curtains.

Guest house in Ocoee

NEW 1BRM Guesthouse | King Bed | Central Florida

Nestled in a private and central location, this newly constructed space offers everything needed for a relaxing stay. The space is perfect for up to four guests, featuring a king size bed, full kitchen, and smart TVs in every room. Enjoy the convenience of high-speed Wi-Fi, a spacious shower, washer / dryer, and a private driveway. Located close to Downtown, Theme Parks, the Stadiums, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for your short term or long term stay.

4.97 out of 5 average rating, 152 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.

4.93 out of 5 average rating, 318 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

Loft in Colonialtown South

A modern living space is highlighted by a plush grey sofa and mid-century styled furniture. A large window invites natural light, showcasing views of the outdoors. Decorative elements, including a small plant and artwork, add character to the room while maintaining a clean aesthetic.

4.92 out of 5 average rating, 657 reviews

Contemporary Loft Near Downtown

Conveniently located between the foodie-friendly Milk District and Downtown Orlando, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is only 20 minutes away, Disney is 35 minutes, MCO 20 minutes.

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, 194 reviews

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.

Guest house in Orwin Manor

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.

4.99 out of 5 average rating, 110 reviews

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)

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, 281 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.

4.93 out of 5 average rating, 274 reviews

A spacious suite is displayed with light blue walls and a full bed featuring striped bedding. A smart TV is mounted on the wall, while a small kitchenette with a refrigerator and a dining area is visible. Natural light enters through a window shaded with blinds.

Guest house in Orlando

"Modern Suite"

"Completly private cozy one-bedroom/bathroom suite with a romantic kitchen & dining area. Centrally located 20 minutes drive from Universal Studios. , 15 minutes to Downtown Orlando, 30 minutes to Disneyworld. Walking distance to Central Florida Fairgrounds, and Chinatown. Book your stay today!" INCLUDED - 1 Full Bed - 1 Full Bathroom - 1 Smart ROKU TV - Wi-Fi 60 Mbps - Kitchen - Refrigerator - Dining table & chairs - 1 Parking Space - AC/Heater -Temperature Range 70°F-79°F

4.94 out of 5 average rating, 150 reviews

A bright bedroom features a spacious bed with a plush headboard and soft linens. Natural light enters through two windows, illuminating the room. A round mirror is mounted on the wall above a minimalistic desk with a chair, adding functionality to the cozy space.

Home in College Park

Priv. Modern Cozy CP 1B/1Ba Suite near DT Orl & WP

Private & Comfortable 1 bd/ba suite in a 2021 townhome with front view windows, queen size bed, walk-in shower& private entrance. Equipped w/ ceiling and portable fans, Roku smart TV, mini fridge/freezer, microwave, and Keurig. Located in a safe, quiet, walkable neighborhood. 5 minutes of College Park shops, 10 minutes from downtown Orlando, 25 minutes to Universal Studios, 30 minutes to Orlando International Airport, & 40 minutes to Disney.

4.89 out of 5 average rating, 166 reviews

A scenic view overlooking Starke Lake is presented, featuring a spacious deck with railing. A tranquil pool is visible in the foreground, while vibrant clouds reflect the colors of a sunset in the background, enhancing the natural beauty of the surroundings.

Home in Ocoee

Lakeview Sunsets with Loft Escape West of Orlando

We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

Shipping container in College Park

An outdoor deck features a round table with two chairs beneath a vibrant orange umbrella. The entrance to the container studio is framed by glass doors, surrounded by plants. String lights are visible overhead, providing a cozy ambiance.

4.93 out of 5 average rating, 191 reviews

Cozy container in College Park and near Downtown

This is a unique stay in a container that has been transformed into a studio. Similar to a tiny home but without climbing into a loft. The Container is outfitted with a Kitchen, Bath and sleeping area. Cozy and quaint is the best way to describe it. The location is in my backyard in College park, near major roadways for easy travel to the theme parks, Winter Park restaurants and Downtown entertainment.

Popular amenities for Pine Hills 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, 166 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 | Downtown

An open living space features a dining area with a modern table set for four. Industrial-style stools provide seating. The background reveals a connected kitchen with stainless steel appliances. Natural light fills the room through large windows, creating a bright and inviting atmosphere.

4.94 out of 5 average rating, 176 reviews

Cozy 3-bedroom home 4-min from Universal Studios

4.94 out of 5 average rating, 190 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

A modern pool house is featured, with large glass doors opening to a swimming pool. The exterior includes a tree emblem and a small seating area with a chair. Sun loungers are positioned near the pool, surrounded by lush grass and a wooden fence.

4.98 out of 5 average rating, 102 reviews

Amazing New Pool House!

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.

4.98 out of 5 average rating, 128 reviews

1924 Spanish Carriage House Lower

The interior showcases a spacious living area featuring contemporary furniture in neutral tones. A large dining table is centrally placed, and natural light filters through expansive windows, enhancing the openness of the space. The enclosed area includes a view of a private pool and hot spa.

4.91 out of 5 average rating, 334 reviews

Mid-century Modern Villa w/ Pool Near Universal

4.92 out of 5 average rating, 165 reviews

The screened lanai pool area is highlighted by a spacious pool and spa, reflecting the vibrant sunset. A serene lake and green yard are visible beyond the enclosure, providing a peaceful backdrop.

Home in Kissimmee

Gorgeous Relaxing Pool Home Near Disney- Pond View

4.88 out of 5 average rating, 133 reviews

The open-plan living area features a sectional couch and a stylish armchair, arranged around a glass coffee table. A large TV is positioned on a console, while natural light filters through sliding glass doors that lead to the patio.

Apartment in Orlando

3BR Condo w Resort Access near Epic Universe

Family- and pet-friendly home rentals

4.85 out of 5 average rating, 173 reviews

Huge pool & Lakeview home | 5 Min Universal

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.

4.96 out of 5 average rating, 165 reviews

Private pool home near Downtown

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, 127 reviews

The Cottage A Pet Friendly Guesthouse

5 out of 5 average rating, 105 reviews

A dining table is set with a tray of assorted cheeses, fruits, and spreads, while glasses sit ready for drinks. Large glass doors reveal views of Bear Lake and a deck with seating, enhancing the inviting ambiance.

Home in Apopka

Magnificent Lakefront Home•Swim&Relax•Long Stay OK

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, 206 reviews

Charming Getaway Near Downtown & Disney

Guest house in Thornton Park

A charming exterior of a cottage-style house is framed by lush greenery and well-kept landscaping. A friendly Golden Retriever stands on the front lawn, which features a mix of plants and decorative elements. A welcoming porch with seating is visible, inviting relaxation.

4.9 out of 5 average rating, 815 reviews

Thornton Park's Historic Guest House - private

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, 467 reviews

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

A spacious living area features light-colored wooden flooring and large windows allowing natural light to fill the space. Two comfortable sofas are arranged around a glass coffee table, and a potted plant adds a touch of greenery. A dining table is visible in the background.

5 out of 5 average rating, 148 reviews

Stay in the best neighborhood in downtown Orlando!

Family-friendly home rentals with a pool

4.87 out of 5 average rating, 606 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 Fern Park

Maitland-Orlando Area, FL. Pool House Bungalow

5 out of 5 average rating, 84 reviews

Home in Oak Ridge

Harmony | Heated Pool | 10 min Universal & Epic.

Superhost

A private enclosed pool is surrounded by a screened patio, offering scenic views of lush greenery and blue skies. The pool is clear and inviting, with sunlight reflecting off its surface, creating a serene atmosphere for relaxation.

4.69 out of 5 average rating, 13 reviews

Scenic View w Pool/Fenced Yard/Centrally located

Superhost

A sleek game room features a pool table and vibrant wall art related to racing and nostalgia. A private pool area is visible outside, offering sun loungers and a scenic backdrop of palm trees. The two-story home displays modern architecture with a welcoming front entrance.

Home in Kissimmee

4.73 out of 5 average rating, 146 reviews

Premium 6 BD/ 6.5 BA Encore at Reunion (7514 MA)

Superhost

5 out of 5 average rating, 6 reviews

Endless Summer, Clear Lake Pool House & Hot Tub

The image showcases an inviting living space with neutral tones and natural light flowing in through large windows. A stylish chandelier hangs above a dining area filled with modern furniture. In the background, a screened pool area is visible, enhancing the outdoor experience.

4.97 out of 5 average rating, 405 reviews

Shadow Bay Luxe / Private Pool Near Universal

4.8 out of 5 average rating, 175 reviews

A comfortable living area is showcased with modern furnishings, including a sectional sofa adorned with colorful accent pillows. A coffee table is positioned on a patterned rug, while large glass doors lead to a balcony offering views of the surrounding area. A wall-mounted television is available for entertainment.

Flat in Orlando

Top-Floor Lakeview Condo at Vista Cay Resort

A sparkling pool is seen surrounded by a spacious patio, featuring a white covered area with comfortable seating. A hammock hangs nearby, offering a shaded space for relaxation. The pool water glimmers under natural light, enhancing the serene atmosphere of the outdoor area.