Pet-friendly holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Park pet-friendly home rentals
Pet-friendly house rentals
Home in Orlando
4.9 out of 5 average rating, 104 reviewsSODO Mid Century Modern Cottage
21–28 Jul
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
28 Apr – 5 May
Home in Orlando
4.94 out of 5 average rating, 124 reviewsThe Orlando Retreat.
1–8 Dec
Home in Orlando
4.94 out of 5 average rating, 374 reviewsPet Welcome/Fully Fenced Backyard/Washer & Dryer
24–31 Aug
Home in Orlando
4.97 out of 5 average rating, 138 reviewsDowntown Orlando -The Modern Zen Studio w/Hot Tub
4–11 Aug
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
10–17 Aug
Home in Orlando
4.82 out of 5 average rating, 152 reviewsKing suite , Modern house perfect for vacation
22–29 Jul
Home in Longwood
4.96 out of 5 average rating, 112 reviewsCozy 3 Bedroom Home, Great location!!
10–17 Nov
Pet-friendly home rentals with a pool
Guest house in Mount Dora
4.9 out of 5 average rating, 707 reviewsKey West cottage of Mt Dora
22–29 Oct
Cottage in Orlando
4.96 out of 5 average rating, 141 reviewsMills Cottage
5–12 Jul
Guest house in Sanford
4.95 out of 5 average rating, 227 reviewsPalmetto Pool Retreat
11–18 Nov
Flat in Winter Garden
4.88 out of 5 average rating, 112 reviewsStay A While
12–19 Jul
Home in Minneola
4.98 out of 5 average rating, 111 reviewsSpacious Home ~ Heated LED Pool & Ping Pong
15–22 Sep
Guest suite in Orlando
4.85 out of 5 average rating, 107 reviews✨️Modern Suite with POOL- Close to All Parks!🎡
26 Nov – 3 Dec
Cottage in Kissimmee
4.98 out of 5 average rating, 140 reviewsRunaway Beach Resort Pet Friendly: Magic Kingdom
20–27 Apr
Home in Orlando
4.86 out of 5 average rating, 157 reviewsPool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
14–21 Sep
Private, pet-friendly home rentals
Guest suite in Orlando
4.78 out of 5 average rating, 525 reviewsPrivate guest suite with enclosed porch
19–26 Jul
Guest house in Orlando
4.93 out of 5 average rating, 267 reviewsCharming Thornton Park Guesthouse
31 Jan – 7 Feb
Guest suite in Orlando
4.84 out of 5 average rating, 195 reviewsPrivate Suite in Mills 50 District with Laundry!
25 Nov – 2 Dec
Tiny home in Orlando
4.85 out of 5 average rating, 220 reviewsThe Getaway NEW Secluded Unique Experience
28 Apr – 5 May
Campervan/Motorhome in Orlando
4.98 out of 5 average rating, 102 reviewsVintage Corner/Near OIA/Private/Self check-in/WiFi
13–20 Jan
Guest house in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
15–22 Aug
Tiny home in Orlando
4.98 out of 5 average rating, 101 reviewsPrivate, Modern & Clean Tiny Home. “La Casita”
29 Nov – 6 Dec
Apartment in Winter Park
4.82 out of 5 average rating, 60 reviewsLovely Winter Park Home close to Hospitals !
20–27 Jan
Quick stats about holiday rentals that are pet-friendly in Winter Park
Total rentals
140 properties
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
5.7T reviews
Nightly prices starting at
₹1,668 before taxes and fees
Destinations to explore
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Tampa Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Holiday rentals
- Naples Holiday rentals
- Fort Lauderdale Holiday rentals
- Miami Beach Holiday rentals
- Miami Holiday rentals
- Key West Holiday rentals
- Pet-friendly rentals Orlando
- Pet-friendly rentals Florida
- Pet-friendly rentals Florida
- Pet-friendly rentals Kissimmee
- Flat rentals Winter Park
- House rentals Winter Park
- Fitness-friendly rentals Winter Park
- Rentals with a firepit Winter Park
- Rentals with a hot tub Winter Park
- Apartment rentals Winter Park
- Rentals with a patio Winter Park
- Rentals with an EV charger Winter Park
- Rentals with outdoor seating Winter Park
- Guest house rentals Winter Park
- Monthly Rentals Winter Park
- Rentals with a fireplace Winter Park
- Family-friendly rentals Winter Park
- Rentals with lake access Winter Park
- Rentals with a washing machine and dryer Winter Park
- Private suite rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with pools Winter Park
- Pet-friendly rentals Orange County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom