Family-friendly vacation rentals in Winter Springs

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winter Springs

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Sanford

4.88 out of 5 average rating, 105 reviews

Edgewater lake house Sanford SFB airport Boombah

This is a beautiful 3 bedroom 2 bath home on Lake Ada. Just 10 minutes to Sanford SFB airport. Clean, uncluttered home equipped with everything you need for a fun vacation, just bring your toothbrush and shampoo. Master bedroom with full bath and direct access to the screen porch. Flat TV in master, BR 3 and the living room and WiFi throughout. In the fenced back yard, there is a fire pit with gate access to the dock and lake. Screen porch and gas grill great for entertaining family and friends.

Guest favorite

Guesthouse in Leesburg

4.98 out of 5 average rating, 364 reviews

Silver Lake Guest Pool House

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

Guest favorite

Home in Sanford

4.97 out of 5 average rating, 234 reviews

Clean, cozy home in a GREAT location

This clean, comfortable home is in a peaceful neighborhood and centrally located to everything you may wish to enjoy while on your Central Florida vacation. Literally two to three minutes away from I-4, highway 417 and a multitude of shopping and dining options. Universal Studios, Sea World and Daytona International Speedway are all within about 40 minutes, while Disney World and Kennedy Space Center are about 50 - 60 minutes. Also easy access to Sanford and Orlando International Airports.

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 298 reviews

A Home Where Eclectic Luxury Meets Affordability

Welcome to the Haven at Temper Wild - 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 (You must notify host if you are bringing a pet prior to booking) Read the rules of the property before booking, to ensure that you are OK with them.

Guest favorite

Tiny home in College Park

4.96 out of 5 average rating, 666 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

Guest favorite

Home in Orlando

4.84 out of 5 average rating, 197 reviews

Waterside Pet Friendly Lakefront

Waterside Estates is a family friendly and safe community. Close to supermarkets, restaurants, entertainment and minutes away from major highways like 417 and 528, just a 15 minute drive from the Orlando International Airport and 45 minutes from the Space Coast!! Disney and Universal are 20-25 mins away. Home is fully equipped with a stocked kitchen to cook. WIFI throughout. Easy Check in and Check out. Property in compliance with Ord. No. 2018-3. NO Garage access. No post surgery guest.

Superhost

Farm stay in Oviedo

4.9 out of 5 average rating, 105 reviews

The Guest House in Oviedo countryside

If you love farm life, The Guest House is the place for you! We invite you to stay in the 600 sq ft apartment, one bedroom & one full bath. Our cozy country getaway is clean, fully furnished & situated on a 5-acre working equine therapy ranch. During your stay, you'll hear all the neighs, moos, bleats and clucks your heart desires! Come see a real farm in action from the comfort of a relaxing space, or while dining al fresco as you enjoy watching the horses go in and out of pasture.

Superhost

Farm stay in Orlando

4.91 out of 5 average rating, 169 reviews

Charming Guesthouse at Pine & Oak Place

Tucked away on a small farm, our Charming Guesthouse offers the comforts of home in a country setting. Whether you are looking for a family friendly getaway or are in town for a business trip, this property has the amenities you are looking for. Located in East Orlando, guests benefit from the privacy of a tucked away setting while remaining in close reach of World Class Theme Parks, Attractions, beaches, and the University of Central Florida. We look forward to hosting you!

Guest favorite

Treehouse in Saint Cloud

4.96 out of 5 average rating, 887 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Guest favorite

Houseboat in Sanford

4.98 out of 5 average rating, 185 reviews

Floating Cottage - Sweet River Retreat in Florida

Welcome to FLOATING COTTAGE . . . Imagine staying in a small cottage, gently afloat on the beautiful St. Johns River in Sanford, Florida. Perfect for social distancing! Sanitized between guests. Contactless check-in. Floating Cottage provides a magical space to relax, refresh and explore. Relax on the front porch; enjoy the warm breeze while watching marina activity, and the bounty of nature. Enjoy the peaceful comfort of the fully equipped small home.

Guest favorite

Guest suite in Altamonte Springs

4.92 out of 5 average rating, 333 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!

Guest favorite

Guesthouse in Maitland

4.87 out of 5 average rating, 386 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