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

4.97 out of 5 average rating, 212 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.

Apr 21 – 28

G$21,364 GYD per night

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 277 reviews

Eclectic Home Where 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.

Jul 24 – 31

G$44,163 GYD per night

Guest favorite

Guest suite in Winter Park

4.96 out of 5 average rating, 245 reviews

Atmospheric Studio in the Garden

Enjoy a little piece of Florida's lush paradise. Full studio suite lives elegantly & comfortably for longer-term stays. We've taken such pride in the opportunity to allow old Florida to intersect with compelling modern design and styling. Relax in this fully furnished studio apartment with kitchenette nestled among a verdant garden. Home boasts modern kitchen, comfy memory foam bed, separate shower and bath & spacious living and entertaining areas. Available for stays of one month or longer.

Jun 15 – 22

G$21,076 GYD per night

Superhost

Farm stay in Orlando

4.9 out of 5 average rating, 159 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!

Mar 31 – Apr 7

G$25,003 GYD per night

Guest favorite

Guesthouse in Mount Dora

4.9 out of 5 average rating, 707 reviews

Key West cottage of Mt Dora

Cozy little cottage located in the gardens of the main house. It has a full kitchen. 1 bath with a jacuzzi tub.. Queen size bed and a couch for a 3rd person. THE LOCATION is 3 MILES between Mount Dora ,Tavares & Eustis a short drive or bike ride to all location. I’m 2.5 blocks off Lake Shore Dr. to beautiful Lake Dora. FRESH eggs from the Easter egg hens for your use ( When available) The eggs they lay are pink, green and blue. They will need to be washed before use..

Mar 4 – 11

G$28,424 GYD 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!

Sep 26 – Oct 3

G$21,832 GYD per night

Superhost

Home in Geneva

4.95 out of 5 average rating, 566 reviews

Danville Family Vacation house

Private Family getaway! You have private use of this comfortable Inn that was featured on HGTV's Million-Dollar Rooms. This is a great value ! It is very spacious and offers a full kitchen. We host overnight guests looking for a truly unique place to stay. Danville Inn is located inside the Downtown Danville Hanger. You are renting the Inn only. The Downtown, pub and patio are common areas and staff use areas. Danville is a glamping experience.

Aug 22 – 27

G$33,057 GYD per night

Guest favorite

Guesthouse in Sanford

4.95 out of 5 average rating, 330 reviews

Bungalow Steps to Downtown Sanford and Lake Monroe

400 sq. ft. 1-rm. Bungalow studio apartment on ground level. Partial view of Lake Monroe can be seen from property. Separate, private entrance. Comfortable one room efficiency studio located steps to Ft. Mellon Park, The Riverwalk on Lake Monroe, Sanford Marina, and downtown Sanford Historic District. Short walking distance to parks, restaurants, unique shops, art galleries, pubs, bus, and free trolley. Free on-site parking.

Jan 20 – 27

G$19,439 GYD 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

Mar 29 – Apr 5

G$24,187 GYD per night

Guest favorite

Guest suite in Orlando

4.93 out of 5 average rating, 562 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.:)

Oct 21 – 28

G$20,448 GYD per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 161 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.)

Aug 13 – 20

G$19,854 GYD per night

Guest favorite

Farm stay in Apopka

4.94 out of 5 average rating, 124 reviews

Entire home, Country feel, close to everything

Mobile home on a 5 acre country setting shared with a couple of goats, (over grown) pot belly pigs and free roaming chickens. We are located half a block from a beautiful city-owned horse riding trail that runs along side a jogging / bike trail. Country living with city amenities minutes away. Limited antenna TV. Coffee and tea provided.

Mar 16 – 23

G$21,886 GYD per night