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
4.92 out of 5 average rating, 102 reviewsSODO Mid Century Modern Cottage
17–24 Jul
Home in Orlando
4.81 out of 5 average rating, 151 reviewsKing suite , Modern house perfect for vacation
6–13 Dec
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
20–27 Dec
Home in Orlando
4.94 out of 5 average rating, 374 reviewsPet Welcome/Fully Fenced Backyard/Washer & Dryer
30 Nov – 7 Dec
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
21–28 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 Orlando
4.91 out of 5 average rating, 117 reviewsLakefront presidential suite / resort pool
9–16 Jun
Home in Orlando
4.9 out of 5 average rating, 164 reviews★ PRIVATE HOME IN DOWNTOWN ORLANDO ★ RETREAT ★
2–9 Dec
Pet-friendly home rentals with a pool
Guest suite in Orlando
4.92 out of 5 average rating, 316 reviewsDowntown Orlando Garden Retreat
16–23 Jun
Guesthouse in Mount Dora
4.9 out of 5 average rating, 705 reviewsKey West cottage of Mt Dora
13–20 Jul
Guesthouse in Sanford
4.95 out of 5 average rating, 226 reviewsPalmetto Pool Retreat
27 Feb – 6 Mar
Cottage in Orlando
4.96 out of 5 average rating, 141 reviewsMills Cottage
5–12 Jul
Apartment in Winter Garden
4.88 out of 5 average rating, 111 reviewsStay A While
17–24 Jul
Cottage in Kissimmee
4.98 out of 5 average rating, 140 reviewsRunaway Beach Resort Pet Friendly: Magic Kingdom
16–23 Sep
Guest suite in Orlando
4.85 out of 5 average rating, 106 reviews✨️Modern Suite with POOL- Close to All Parks!🎡
25 Nov – 2 Dec
Condo in Orlando
4.97 out of 5 average rating, 296 reviewsLuxurious Waterfront Resort near Disney &Universal
31 Aug – 7 Sep
Private, pet-friendly home rentals
Guest suite in Orlando
4.83 out of 5 average rating, 192 reviewsPrivate Suite in Mills 50 District with Laundry!
9–16 Sep
Guesthouse in Orlando
4.96 out of 5 average rating, 366 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
31 Dec – 7 Jan
Guest suite in Orlando
4.94 out of 5 average rating, 195 reviewsLuxury Suite Near Disney & Downtown Orlando
2–9 Jul
Guest suite in Orlando
4.9 out of 5 average rating, 153 reviews✪ Stylish ✔Location ✔Netflix ✔Parking ✔Wifi
21–28 Aug
Tiny home in Orlando
4.85 out of 5 average rating, 220 reviewsThe Getaway NEW Secluded Unique Experience
24 Feb – 3 Mar
Condo in Winter Park
4.81 out of 5 average rating, 59 reviewsLovely Winter Park Home close to Hospitals !
27 Mar – 3 Apr
Guesthouse in Orlando
4.95 out of 5 average rating, 42 reviewsNew Mid Century-Modern Studio
18–25 Jun
Condo in Winter Park
4.94 out of 5 average rating, 35 reviewsChic Lake & Poolside Retreat in Winter Park
1–8 May
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
5.7K reviews
Nightly prices starting at
$34 NZD 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
- Monthly Rentals Winter Park
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- Guesthouse rentals Winter Park
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- Pet-friendly rentals Orange County
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