Family-friendly vacation rentals in Pine Hills

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pine Hills

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Guest favorite

Home in Orlando

4.87 out of 5 average rating, 195 reviews

Charming Orlando Cottage - Close to Everything!

This charming 1920's cottage is the perfect retreat for either a brief stay visiting all that Orlando has to offer, or could be a quiet escape to stay for a few months working remotely. The home has one king size and one queen size bed, a separate office if you are needing to work out of the home. It's a private space but on a larger piece of property that also has two other homes and shares access to a beautiful lake - which our guests are welcome to use! Inquire for different terms available.

Jul 21 – 28

R2,517 ZAR per night

Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 389 reviews

Garden House near Orlando's cultural hub

On a quiet cobblestone street, yet close to art and culture, more than 3 dozen restaurants in walking distance, Florida Hospital and family-friendly activities. You’ll love our place because of the location, the large bathroom with jacuzzi, the skylights, window seat, porch swing. It is nestled in our back yard surrounded by trees and has its own private entrance via a rustic walk way of pavers and stones. Couples, families, most anyone will find it charming. STR 1009942 (City registration)

May 23 – 30

R1,950 ZAR per night

Guest favorite

Tiny home in Orlando

4.95 out of 5 average rating, 620 reviews

Quiet Shed in Downtown

Nestled behind my 1920s bungalow in one of Orlando’s best neighborhoods, The Shed is a local experience and retreat. Located in the city center, just a 5 min Uber to Amway, Soccer Stadium, and walking distance to the Sun Rail and hospital, you’ll love The Shed, because of its chill vibe and privacy. Perfect for couples, traveling professionals, and those new to Airbnb. Note: I rent my main house so you may see those guests in the backyard. No smoking/vaping allowed. Early check-in @ $20/hr

Dec 12 – 19

R2,301 ZAR per night

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 370 reviews

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

Pet-friendly 2 Bedroom/3 Bath House. Designed by renowned architect James Gamble Rogers II, the house is a 25-minute drive ($23 Uber) from the MCO Airport. Nestled in the heart of Orlando's College Park district, it is an oasis just moments away from Downtown Orlando: nightlife, museums, and funky art and music scene. Take a 25-minute drive into Disney, Universal, or The Outlets. Uber/Lyft/Walk to nearby trendy restaurants, museums, theaters, boutique shopping, and our craft beer scene.

Jul 13 – 20

R3,298 ZAR per night

Guest favorite

Home in Orlando

4.95 out of 5 average rating, 314 reviews

*HALF HOME* (read desc) Pool/Disney/Universal

We LOVE hosting! Think of us as friends you’re staying with, but haven’t met yet. We are happy to interact, but also happy to remain out of sight to ensure your privacy. We live in the master (on OTHER SIDE w/own bath) when not traveling and we DO use kitchen. Everything else is exclusive to you! You get plenty of space & PRIVACY. Photos represent YOUR space (we use kitchen too, but rest is exclusive) If you’re not comfortable with on-site host w/kitchen usage, we aren’t right choice.

Aug 23 – 30

R2,072 ZAR per night

Guest favorite

Guest suite in Orlando

4.95 out of 5 average rating, 158 reviews

Upscale Urban Chic Apartment

This warm “Carriage House Apartment” offers a cozy relaxed studio suite, it's 500 sq ft in a premiere established neighborhood. Built in 1938, updated for modern fine living with charm. Enjoy scenic views, romantic evening strolls through tree lined streets to nearby parks and lakes. Ample on street parking. Walking distance to shopping, bars, fine dining, the Orlando Regional Medical Center and near major attractions. Live a local’s life in the heart of Orlando, Florida.

Jun 3 – 10

R2,372 ZAR per night

Guest favorite

Guest suite in Altamonte Springs

4.92 out of 5 average rating, 316 reviews

The Bungalow

Welcome to your home away from home! Enter through a private driveway and enjoy the ease of keyless entry. Located across the street, Sanlando Park offers walking trails, basketball and popular tennis courts. Whether your interests are peace and quiet or adventure, you are only 30 minutes or less away from our beautiful natural springs, beaches and all major attractions. Wake up with the sunshine, put on a pot of coffee and welcome to Florida!

Oct 25 – Nov 1

R1,969 ZAR per night

Guest favorite

Guesthouse in Windermere

4.94 out of 5 average rating, 240 reviews

Small Guesthouse near Orlando's Theme Parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

Mar 21 – 28

R2,556 ZAR per night

Guest favorite

Guesthouse in Maitland

4.87 out of 5 average rating, 381 reviews

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

Aug 29 – Sep 5

R2,132 ZAR per night

Guest favorite

Guest suite in Orlando

4.93 out of 5 average rating, 563 reviews

Charming Comfortable Cottage in College Park

Welcome to the 1942 Cottage. This quaint cottage boasts an outdoor table, screened front porch, living room , bathroom, and a comfortable oversized bedroom that has a microwave, refrigerator/ freezer, and Keurig coffee maker all for your private use. PLEASE note, I live in the actual back of the cottage, like a bnb. It’s an older home with a few quirks but it’s comfortable and clean.:)

Sep 30 – Oct 7

R1,849 ZAR per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 162 reviews

Private Backyard Cottage in Mills50

Airy one-bedroom garden cottage in Orlando's hippest historic neighborhood. Walk or bike to great restaurants, parks, and bars. Located 5 to 10 min to Downtown Orlando, Florida Hospital, and Winter Park; 20 to 30 min to Universal, Disney, and UCF. Recently upgraded with queen bed, stove, and access to brand-new washer/dryer. (City of Orlando Short-Term Rental registered.)

Oct 20 – 27

R1,950 ZAR per night

Guest favorite

Guest suite in Orlando

4.91 out of 5 average rating, 458 reviews

lovely room apartment. It's not shared.

This place is located in Central Orlando. Its located in a quiet and secure neighborhood. Its also a few min from Florida mall ,restaurants, food stores, International Dr , The convention Center is 6.5 miles , Theme parks as Universal Studios is 6 miles and Disney is about 25 minutes. The Orlando International airport is 6.5 miles from the house.

Jun 21 – 28

R1,400 ZAR per night