Family-friendly holiday rentals in Maitland

Wekiva Riverfront Home with Dock Close to Springs!

NEW PHOTOS COMING SOON!! Adventure awaits you and your family at the Wekiva River Retreat! This beautiful home is nestled in the heart of real Florida and sits directly on the banks of the Wekiva River. You and your family can explore the natural landscape in our fleet of Kayaks and canoes, or walk to the Rock Springs Run State Park for hiking, biking, and trail riding. Finish the eventing under the stars around our large fire-pit roasting marshmallows, or watching movies on our big screen tv.

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.

Charming 2BR Cottage, Downtown Orlando

Bright, cozy 1940’s cottage located in a quiet, safe, family-friendly Downtown Orlando neighborhood. 2 bedroom, 1 bath, onsite parking, full kitchen, washer and dryer, fenced-in back yard and patio area, working desk space in bedroom. Walking distance to the local gems and eateries of Audubon Park and the Mills 50 District! Central location minutes away from Winter Park and Downtown local attractions. 20-30 minutes from Universal, Disney and MCO. Great for a work trip or an Orlando getaway!

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.

Apt C -Modern Elegance in the Heart of Winter Park

Light, bright and full of delight! Fastest internet speed available: 154MBPS download and 20 MBPS upload! Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Heated pool , poolside grill and bikes for your enjoyment! Three blocks to Park Ave and two blocks to the Winter Park Village! Simple elegance downtown defined by contemporary design and leisurely living. Enjoy the convenience and tranquility of one of Florida's best walking communities

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!

Paradise nook 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.

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.