Pet-friendly holiday rentals in Winter Springs

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winter Springs

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

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Top guest favourite

Home in Kissimmee

4.92 out of 5 average rating, 133 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

Disney Playhouse – Your Dream Vacation Awaits! Indulge in elegance and comfort at this newly upgraded, pet-friendly retreat. Relax in your private pool & spa within a fully fenced backyard. Unwind in the plush master suite, enjoy Roku TVs in every room, and stay connected with blazing fast 1GB WiFi. The Diner Themed game room features a Marvel electronic pinball machine, pool table, and Wii. Pool heat is optional, hot tub always free! Pets welcome. King Master. Book your luxury getaway today!

Superhost

Flat in Orlando

4.8 out of 5 average rating, 127 reviews

NEW Designed Apt 2024 NrUCF PETSOk PrivateEntry

Discover this luxurious, newly renovated Airbnb studio with a FULLY PRIVATE patio featuring a hammock under a shady mango tree. Enjoy PRIVATE LAUNDRY, patio seating, and umbrella. The fenced backyard ensures privacy, minutes from UCF, Universal, Disney, and local amenities. The studio sleeps 4 and is part of a property with a house and a separate private apartment, each with its own kitchen, bathroom, bedroom, sitting room, garden hammock, patio, and entry. Experience tranquility in a quiet area

Guest favourite

Home in Clermont

4.84 out of 5 average rating, 223 reviews

Great House w/Heated Pool;Near all Parks!

Welcome to la Casita de todos! This home will be your home away from home, children-friendly, and spacious for the whole family! Dogs under 20 pounds are allowed with a 75 USD fee per pet. HEATED pool with a charge fee of $ 25 USD per day. BBQ grill has an extra charge of $40 USD (for the whole stay, including 1 propane gas and cleaning). After booking and before check-in please let me know if you are bringing a pet or will use the BBQ. Locations nearby: Walmart 0.5 miles. Dollar Tree 0.1 miles.

Top guest favourite

Cottage in Mount Dora

4.93 out of 5 average rating, 104 reviews

Cozy Cottage 3 blocks from town

Come as guests, leave as friends. This super-clean 1 bed, 1 bath cottage sleeps up to 4 adults. "Cozy Cottage" is pet friendly and laid back with a super-fast internet connection. Historic Mount Dora is only steps away. Enjoy the many quaint shops, restaurants and regional festivals. The rolling hills and lakeside views give this town its New England seaside charm. Orlando theme parks are only 1 hour away. We are the perfect place to retreat after the hustle and bustle of the theme parks.

Superhost

Bungalow in Mount Dora

4.64 out of 5 average rating, 11 reviews

Casita Encanta-Dora, Steps to town, Pet-Friendly

Enjoy a stylish experience at this centrally-located one of a kind Sears Built 1950’s bungalow. Just a 2 minute walk to Lake Dora and the Marina and a 5 minute walk to Donnelly Street for all of your shopping, entertainment and dining experiences . This pet-friendly, two bedroom home offers a fully fenced in front yard, two king size beds, a twin size daybed and a down filled living room couch with a chaise lounge . The loft area is set up for the little ones with a night light and books

Guest favourite

Home in Orlando

4.85 out of 5 average rating, 206 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.

Top guest favourite

Guest house in Sanford

4.95 out of 5 average rating, 270 reviews

Palmetto Pool Retreat

The Palmetto Pool Retreat offers complete privacy - detached studio cottage, with a pull-down Queen Murphy bed. * Kitchen - refrigerator, stove, cookware, Keurig , microwave, toaster, dishes and utensils. * Studio Living area - Queen size Murphy Bed, Roku TV, WiFi Internet, AC/Heater; Closet, Iron. Please don’t put AC lower than 72. * Private Bathroom - shower, hairdryer. *Outdoors - Pool, not heated, with private double patio sitting area with 2 Fire pits Gas & Wood; BBQ gas grill

Guest favourite

Bungalow in Mount Dora

4.86 out of 5 average rating, 104 reviews

Renovated "Cozy Bungalow" in Downtown Mt. Dora!!!

The perfect place to stay while visiting beautiful Mount Dora. Just a short walk or bike ride (provided) to historic downtown Mount Dora. Enjoy all the nearby shops, cafes and galleries. Located in an established neighborhood amongst other renovated historical cottages. Walk to the library, parks and to Lake Dora at sunset. Built in 1948, this inviting 2 bedroom 2 bath home has been recently renovated. The kitchen is fully equipped with a mini fridge, microwave, coffee maker, and stove.

Top guest favourite

Home in Maitland

4.94 out of 5 average rating, 163 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Top guest favourite

Home in Mount Dora

4.98 out of 5 average rating, 132 reviews

Spacious, modern and cozy , close to downtown.

Comfy, clean and cute! Only 5 min drive to downtown. The house is one story and located in a quaint neighborhood. Inside as you entered there is a spacious living room with a L shaped couch overlooking the beautiful modern electric fireplace and large TV. Great layout with Master on one side and the other two bedrooms on the other side. Kitchen is fully stocked with all you need. Outside there is a porch in front, a large covered lanai in the back and big fenced yard for your pets.

Guest favourite

Cottage in Umatilla

4.95 out of 5 average rating, 128 reviews

Heartwarming Authentic Cottage for Family Joy!

The Cute and Clean Little Cottage you are looking for! Pleasant getaway! ❤️ Heartwarming Authentic Cottage for joyful stays! Near to springs and Manatee watch areas, Ocala Forest, Fishing 🎣 equestrian 🐎 activities, Mount Dora & 🪑Antiques Markets. Just 39 miles to Orlando & Disney and 43 miles to the beach 🏖 Entire Place! Pet Friendly! Free Parking! 2 bedrooms + 2 full baths! Original wood floor in master bedroom and Kitchen! No carpet floors! Nice quiet, safe neighborhood!

Superhost

Home in Altamonte Springs

4.82 out of 5 average rating, 128 reviews

Quiet Place, convenient to everything!

Spacious home in a very quiet residential neighborhood. Perfect home away from home for your special getaway. Vacations, business trips, wedding groups, graduations have all been hosted in the past, and everyone had a great time. There's significant value in having your own quiet place and multiple rooms in a family-friendly setting. DO NOT BOOK MY QUIET PLACE IF YOUR PLAN INCLUDES ANY LARGE GATHERING WHICH MIGHT IMPACT MY HOME OR NEIGHBORHOOD. YOUR RESPECT IS EXPECTED.