Vacation rentals in Oakland
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Top-rated vacation rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness, and more.
Farm stay in Winter Garden
4.95 out of 5 average rating, 44 reviewsCarriage House Studio Apt Peaceful & Private Ranch
Carriage House Studio Apartment on peaceful and quiet horse ranch located one block from the West Orange Trail and one mile to historic downtown Winter Garden featuring Saturday morning Farmer’s Market, casual and fine dining, unique shops, brewery and local theater. Best small town in Central Florida Experience peace & tranquility surrounded by large oak, horses (big & mini), mini pigs and two friendly dogs Perfect for couples, solo and business travelers, traveling nurses, college internships
Nov 20 – 27
Apartment in Clermont
4.93 out of 5 average rating, 246 reviews1 bed/1 bath cozy apt. full kit. pvt. ent. New AC.
This is a 1 bedroom 1 bath apartment with a private entrance, full bath, full kitchen with full-size appliances. Located in downtown Clermont, Florida. Convenient to all central Florida Theme Parks (40 min. drive), shopping including groceries, clothing, electronics, gas, jewelry, pharmacies, theater, and many more. The new Carrier AC system has an internal UV light, BiPolar Ionization system and 1900 Filtrete filter that all kill and remove bacteria, viruses, and mold in the air .
Jun 7 – 14
Home in Winter Garden
4.92 out of 5 average rating, 164 reviewsCozy 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.
May 1 – 8
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oakland vacation rentals
Other great vacation rentals in Oakland
Guesthouse in Winter Garden
4.94 out of 5 average rating, 47 reviewsBlue Heron Bungalow
Jul 11 – 18
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
Jul 4 – 11
Apartment in Windermere
4.83 out of 5 average rating, 52 reviewsPrivate Garage Apt., 5 Miles from Disney World
Oct 7 – 14
Cottage in Winter Garden
4.89 out of 5 average rating, 84 reviews3 br/2 ba Downtown Winter Garden Cottage w\fence
Mar 22 – 27
Guesthouse in Winter Garden
4.96 out of 5 average rating, 25 reviewsGuest house in Winter Garden
May 22 – 29
Cottage in Clermont
4.96 out of 5 average rating, 54 reviewsA-Frame Cottage near Disney, Universal, & Lakes
Aug 21 – 28
Apartment in Minneola
4.98 out of 5 average rating, 44 reviewsSpacious Apartment In Minneola
Apr 27 – May 4
Villa in Clermont
4.89 out of 5 average rating, 38 reviewsCute N Cozy Villa near Disney, pool, Wi-Fi
Jul 6 – 13
Apartment in Ocoee
4.96 out of 5 average rating, 47 reviewsCompletely Private and Cozy Studio
Aug 8 – 15
Guesthouse in Groveland
4.93 out of 5 average rating, 68 reviewsThe Blue Apartment - Country living & lake access.
Oct 15 – 22
Apartment in Clermont
4.94 out of 5 average rating, 47 reviewsRelaxing 1-Bedroom Farm Retreat. Pets welcome!
Oct 15 – 22
Guest suite in Apopka
4.97 out of 5 average rating, 30 reviewsPrivate Deluxe Apartment, 1000 sqft with pool
May 19 – 26
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