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

Guesthouse in Orlando

4.9 out of 5 average rating, 611 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! One of the things I've personally love is finding new experiences in each city I travel to. Orlando has some amazing neighborhoods that most people don't know about because they stay near the Convention Center or the theme Park hotels... Here's a great spot that's close to the parks/convention center but also only a few blocks to Lake Eola, located in one of the most beautiful neighborhoods in FL

Aug 26 – Sep 2

G$18,408 GYD per night

Guest favorite

Apartment in Orlando

4.93 out of 5 average rating, 102 reviews

Apartment, 7 Min to Orlando Airport/ Lake Nona

Complete private unit . A Private Door inside the room to step out to the pool .1 Bed/1 Bath, 2 TV’s , Netflix Amazon, sitting area, and and a small kitchen, We a Manual Slingshot available for rent, the rent for the Slignshot will be $200 per day. Pool area will be available all the time .We just build a door inside the room that way is easy access. This place is 25 Minutes driving to Disney World and most Parks, Lake Nona is 10 minutes away. We are Close to UCF, lake Nona, MCO, Waterford lakes

Oct 14 – 21

G$24,082 GYD per night

Guest favorite

Home in Winter Park

4.92 out of 5 average rating, 105 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.

Aug 9 – 16

G$85,359 GYD per night

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 276 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.

Sep 11 – 18

G$37,284 GYD per night

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 367 reviews

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.

Dec 10 – 17

G$37,315 GYD per night

Guest favorite

Guesthouse in Orlando

4.91 out of 5 average rating, 145 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.

Sep 9 – 16

G$28,080 GYD per night

Guest favorite

Home in Orlando

4.93 out of 5 average rating, 151 reviews

Cozy Downtown Orlando House

Your home away from home. Close to Downtown Orlando and just minutes to all the major theme parks. Private entrance with keypad entry. Private patio with seating. Full kitchen. Private Washer/Dryer. Great access to many local bars, restaurants, and entertainment within walking distance and many more a short drive away. Disney, Universal, Orlando International Airport, Orange County Convention Center are all within a half-hour drive. Only an hour from the beach, Kennedy Space Ctr., etc.

Aug 27 – Sep 3

G$27,217 GYD per night

Guest favorite

Home in Winter Garden

4.92 out of 5 average rating, 167 reviews

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

Apr 19 – 26

G$26,076 GYD per night

Guest favorite

Guest suite in Orlando

4.95 out of 5 average rating, 114 reviews

Charming Getaway Near Downtown & Disney

Relax and enjoy a quiet & newly remodeled private guest suite centrally located near Downtown Orlando. Features a full kitchen, spacious living area & luxurious queen bed for a peaceful & enjoyable stay. Private 2nd story entrance 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.

Jul 25 – Aug 1

G$24,622 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

Feb 15 – 22

G$24,107 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.:)

Aug 2 – 9

G$24,411 GYD per night

Guest favorite

Guest suite in Orlando

4.97 out of 5 average rating, 384 reviews

Vacation & Oasis Mood with #1 location - Pool

From our family to you, we are welcoming you in our Home into our private Orlando, Florida, Oasis :-) Located a very short commute to some of the world most famous tourist attraction, Disney & Universal studio to the privacy of our fully equipped Guest area. We want to make sure that your stay to our home will be memorable and we want to see you again :-)

Apr 18 – 25

G$23,940 GYD per night