Oakland Pet Friendly Vacation Rentals & PickleTrip Homes
Book a Dog-Friendly Rental in Oakland for Your Next Adventure
9.8
(12 Reviews)
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- Pet Friendly
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Apartment
8.8
(7 Reviews)
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10.0
(9 Reviews)
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7.4
(26 Reviews)
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10.0
(8 Reviews)
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House
New
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10.0
(3 Reviews)
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- Pet Friendly
9.8
(22 Reviews)
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- Pet Friendly
9.2
(10 Reviews)
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- Pet Friendly
New
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- Pet Friendly
New
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- Pet Friendly
New
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- Pet Friendly
- TV
New
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New
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- TV
New
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New
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- TV
10.0
(27 Reviews)
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- Pet Friendly
10.0
(12 Reviews)
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- Pet Friendly
10.0
(1 Review)
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- Pet Friendly
- Security/Safety
9.4
(18 Reviews)
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- Pet Friendly
New
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New
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New
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9.8
(6 Reviews)
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- Pet Friendly
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About Oakland Pet Friendly Vacation Rentals on PickleTrip
PickleTrip™'s pet-friendly rentals in Oakland are perfect for pet owners who want to bring their furry friends and enjoy their next pickleball game on vacation. You can rest easy knowing that your pet is welcome and comfortable in your rental. With a variety of options to choose from, you can find the perfect accommodation that fits your needs and budget. Whether you're looking for a cabin in the woods, a beachfront villa, or a luxury resort, PickleTrip™ has a pet-friendly rental that will suit your needs.
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Frequently Asked Questions About Oakland Pet-Friendly Rentals
There are a lot of options in Oakland. If you plan on staying in the Oakland area, consider making a reservation for a few nights at one of these properties as these have been rated the top Pet Friendly Vacation Rentals in Oakland:
- StylishAptWtrGrdnOppLake&Prk&Yrd
- WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn
- Mid Century Hipster
- Modern Florida Bungalow: 3 Miles to Winter Garden!
- Quaint 1Br/Ba entire guest house in heart of Hist. Downtown Winter Garden
- Enchanted 2 Bedroom Home near Downtown Winter Garden
- Central Florida's Historic Gem & wedding venue- The Oakland Manor House
- House with large deck, walking distance to Historic Downtown Winter Garden
- Enchanted 3 Bedroom Home near Downtown Winter Garden
- The Oak View Place.
There are more than 29 pet-friendly rentals available on PickleTrip. Check prices and availability in Oakland and last updated on November 2025. Check an individual property if they have restrictions on the size or numbers of pets.
There are many dog-friendly vacation homes available in Oakland. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Oakland:
Most definitely! There are many luxury places to stay in Oakland. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Oakland. Though note, more expensive is not always better.
The average price of a pet-friendly vacation home is $232. Find our pet-friendly accommodation near Oakland.
At PickleTrip, many of our accommodations are perfect for families and allow dogs too. Check out the complete list of pet-friendly holiday rentals in Oakland to find what works for you.
Finding the best prices in Oakland
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