Family-friendly holiday rentals in Winter Park

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)

Bright and Cozy Orlando Home - Close To It All

NOTHING IS SHARED, very private with your own entrance. Bright, cozy 1 bedroom home accommodates 4 people. Full kitchen featuring all amenities. Central location 15 minutes from the airport, 15 minutes to downtown Orlando, 30 minutes to Disney, Universal, SeaWorld. Your own driveway fits 2 cars, fresh sheets, towels, coffee! Free WiFi and Smart TV (Netflix, PrimeVideo). 1 queen bed + 1 queen futon sofa bed comfortably sleeps 4. We live close by so if you need anything you can always call us.

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.

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

A Home Where Eclectic Luxury Meets Affordability

Welcome to The Altamonte House. Your home away from home. We offer fully free amenities, luxury bedding and pillows, and quintessential design throughout the rooms and home. There are work spaces in every bedroom, ultra-fast wifi, games galore, and a beautiful outdoor space equipped with outdoor dining and lounging. 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.

Tiny House Shed in Downtown

Nestled behind my 1920s bungalow in one of Orlando’s best neighborhoods, The Shed is a local experience. Located in the city center, just a 5 min Uber to Amway, Soccer Stadium, and walking distance to the Sun Rail and hospital. * There is construction at the house next door during daylight hours; expect noise . 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.

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!

ManCave apartment

When the world seems crazy, sometimes you need to escape. The venues are separated on thirty acres. This is my Man Cave located in my airplane hanger. An eclectic collection of stuff is hung from the ceiling and walls. This is a fun space with a bar, microwave, satellite-TV, fireplace, Wi-Fi and air conditioning. The bed is located in the loft. Danville is a glamping experience.

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.