Pet-friendly vacation rentals in Winter Park

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winter Park

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

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Guest favorite

Home in Winter Park

4.93 out of 5 average rating, 113 reviews

A Rare Jewel in the heart of Winter park. Can walk

This lovely 3 bedrooms, 2 bath house is located in the most desirable area of Winter Park. Only few steps from Park Ave. You can walk to all the restaurants, Wine room, coffee shops, stores, art galleries, Museum, Park, Rollins College, Winter Park Community Center. Its only 25 minutes drive to the airport, 45 minutes to the beach, and close to family-friendly activities, nightlife, public transport. This house is great for families, couples, solo adventurers, business travelers, and big groups.

Guest favorite

Guesthouse in Thornton Park

4.89 out of 5 average rating, 684 reviews

Thornton Park's Historic Guest House - private

Please, read my reviews so you know what to expect when staying at the Thornton Park Guest House! Jackson, our Golden Retriever, is the real Super Host! Come join us for a weekend getaway, work trip or just so you don’t have to drive home after a fun night! We welcome all to stay with us! Orlando has some amazing historic neighborhoods that most people don't know about! Here's a great spot that's only a few blocks to Lake Eola, located in one of the most beautiful neighborhoods in FL!

Guest favorite

Rental unit in College Park

4.92 out of 5 average rating, 106 reviews

College Park/Winter Park separate 1 bed/bath 32804

255 sq ft- 1 bedroom w/ queen bed, office space, kitchenette, large bathroom, private entrance in your own yard area. This gem is super clean, the unit is quiet w/ complete blackout in bedroom, bathroom has tons of natural light & 3 shower heads, microwave, fridge & Keurig. Comfy, near I-4 exit 44 Par St. Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando Ballet School 1.5 mi AdventHealth Orlando 0.6 mi AdventHealth Winter Park 3.4 Orlando Health & Arnold /Winnie Palmer 3.8 Rollins College 2 mi

Guest favorite

Rental unit in Orlando

5 out of 5 average rating, 117 reviews

Parent's Retreat!

Whether working in the area, visiting your student or catching a UCF Sporting event. This pet friendly "Parent's Retreat" is just what you're looking for. Located less than 2 miles from campus. this apartment is a great place to land at the end of the day. Kitchen includes microwave, fridge, coffee maker and air fryer. This 380 sq ft newly remodeled mother-in-law suite has private entrance, patio and yard. Suite is completely closed off from the house and has keyless locks for easy check in.

Guest favorite

Guest suite in Orlando

4.95 out of 5 average rating, 132 reviews

Private guest unit W/Tropical Views! (Not shared)

A Queen sized bed awaits you as you enter the private unit overlooking a tropic themed backyard! Included is a full washer/dryer, bathroom w/ bidet, brick fireplace, Wi-Fi, TV, microwave, coffee maker and mini fridge. Just steps from the driveway is a private front door which faces the street (no walking to the back/side yard).The property is within 10 minutes of Inter&Co & Camping world Stadiums, Kia Center, Downtown, Central Florida Fairgrounds & 15 min. to Universal & 30 min. to Disney!

Guest favorite

Guesthouse in College Park

4.91 out of 5 average rating, 163 reviews

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

Guest favorite

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.

Guest favorite

Guesthouse in College Park

4.97 out of 5 average rating, 119 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. We are located in College Park of Orlando. The main road here is Edgwater Drive which offers restaurants, bars, and boutique shops. This location is 15 min. from downtown, 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals in central Florida. Also, you are within walking distance from the historic Dubsdread Golf Club and restaurant. Perfect home away from home.

Guest favorite

Guest suite in Orlando

4.92 out of 5 average rating, 127 reviews

Grey House near Orlando Universal Parks

Your family will be close to everything when you stay at this centrally-located place. The neighborhood is located just 17 min from the MCO airport. Also Downtown Orlando will be only 10 min from your Airbnb and even more, you can also find UCF just 14 min away. Universal Studio, Volcano Bay, and Islands of Adventure Them Parks are only 20 min away. The Aquatic Park Sea World will find it 28 min away. And the amazing Disney Parks located 35 min away. Traffic is moderate.

Guest favorite

Guest suite in Orlando

4.92 out of 5 average rating, 348 reviews

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

Guest favorite

Guest suite in College Park

4.92 out of 5 average rating, 213 reviews

Luxury Suite Near Disney & Downtown Orlando

Come enjoy a cozy & newly-renovated private guest suite centrally located near Downtown Orlando. Features a full kitchen, spacious bathroom, & luxurious queen bed for a peaceful & enjoyable stay. Private entrance, driveway and front porch, and convenient self check-in. Perfectly located walking distance from restaurants, shopping, and parks in a safe and family-friendly neighborhood. Easy access to Downtown Orlando, Theme Parks, and Winter Park/Park Ave.

Guest favorite

Guesthouse in College Park

4.91 out of 5 average rating, 143 reviews

Cozy Escape in the Heart of Orlando w/ Fire Pit

Enjoy a peaceful getaway in this private, pet friendly guest suite. Awake refreshed and ready for a day of exploring Florida. Head out and wander east to beautiful beaches, west to the best theme parks, or stay close in the heart of Orlando and enjoy restaurants, shops, and parks (all in walking distance). After a day of fun, come back and roast some hot dogs or s’mores under the stars in our paver fire pit.