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.

Guest favorite

Farm stay in Winter Garden

4.95 out of 5 average rating, 44 reviews

Carriage 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

$129 per night
Guest favorite

Apartment in Clermont

4.93 out of 5 average rating, 246 reviews

1 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

$91 per night
Guest favorite

Home in Winter Garden

4.92 out of 5 average rating, 164 reviews

Cozy 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

$94 per night

Popular amenities for Oakland vacation rentals

Stay near Oakland's top sights

DG Doughnuts4 locals recommend
West Orange Trail Bikes and Blades22 locals recommend
Killarney Station3 locals recommend

Other great vacation rentals in Oakland

Guest favorite

Guesthouse in Winter Garden

4.94 out of 5 average rating, 47 reviews

Blue Heron Bungalow

Jul 11 – 18

$89 per night
Guest favorite

Home in Winter Garden

4.94 out of 5 average rating, 17 reviews

Cozy home in Winter Garden

Jul 4 – 11

$116 per night
Superhost

Apartment in Windermere

4.83 out of 5 average rating, 52 reviews

Private Garage Apt., 5 Miles from Disney World

Oct 7 – 14

$99 per night
Guest favorite

Cottage in Winter Garden

4.89 out of 5 average rating, 84 reviews

3 br/2 ba Downtown Winter Garden Cottage w\fence

Mar 22 – 27

$150 per night
Guest favorite

Guesthouse in Winter Garden

4.96 out of 5 average rating, 25 reviews

Guest house in Winter Garden

May 22 – 29

$138 per night
Guest favorite

Cottage in Clermont

4.96 out of 5 average rating, 54 reviews

A-Frame Cottage near Disney, Universal, & Lakes

Aug 21 – 28

$122 per night
Guest favorite

Apartment in Minneola

4.98 out of 5 average rating, 44 reviews

Spacious Apartment In Minneola

Apr 27 – May 4

$73 per night
Guest favorite

Villa in Clermont

4.89 out of 5 average rating, 38 reviews

Cute N Cozy Villa near Disney, pool, Wi-Fi

Jul 6 – 13

$110 per night
Guest favorite

Apartment in Ocoee

4.96 out of 5 average rating, 47 reviews

Completely Private and Cozy Studio

Aug 8 – 15

$69 per night
Guest favorite

Guesthouse in Groveland

4.93 out of 5 average rating, 68 reviews

The Blue Apartment - Country living & lake access.

Oct 15 – 22

$95 per night
Guest favorite

Apartment in Clermont

4.94 out of 5 average rating, 47 reviews

Relaxing 1-Bedroom Farm Retreat. Pets welcome!

Oct 15 – 22

$78 per night
Guest favorite

Guest suite in Apopka

4.97 out of 5 average rating, 30 reviews

Private Deluxe Apartment, 1000 sqft with pool

May 19 – 26

$95 per night

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