Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Farm stay in Winter Garden

4.96 out of 5 average rating, 45 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

24–31 Aug

$182 SGD per night

Guest favourite

Guest house in Clermont

4.98 out of 5 average rating, 101 reviews

Downtown Apartment - Walk to Lake, Shops & Dining

This stylish apartment, in Downtown Clermont is @ the center of the coast-to-coast bike trail. Enjoy the quaint lake town experience to the fullest without having to drive anywhere. Lakefront, breweries, retail, dining- all within a 3 min walk! Best features indoors include comfy beds, a double shower, smart TV, & cozy aesthetics. The space is well stocked w/ all the essentials. Small appliances for cooking include an air fryer, crockpot & skillet. Garage storage available 4 recreational gear.

18–25 May

$181 SGD per night

Guest favourite

Home in Winter Garden

4.92 out of 5 average rating, 165 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.

29 Mar – 5 Apr

$153 SGD per night

Guest favourite

Townhouse in Clermont

4.93 out of 5 average rating, 191 reviews

Paradise Escape

Your paradise escape is finally here! In the Sunshine State, paradise is just one perfect cocktail away. Leave your worries away and relax - you are in a sunshine state of mind! My "paradise island" is conveniently located in the heart of Clermont. You will certainly enjoy the welcoming and colorful ambiance! Combination lock instructions will be sent after arrival time confirmation. I look forward to hosting all my guests and making sure that they have an unforgettable experience!

22 Feb – 1 Mar

$145 SGD per night

Guest favourite

Cottage in Winter Garden

4.99 out of 5 average rating, 105 reviews

Come Stay In The Heart Of Winter Garden

Stay in a completely renovated 1937 cottage that's located in the heart of historic downtown Winter Garden. It's walking distance from all of the shops, restaurants, and events (including the #1 rated farmers market in the nation every Saturday) that make Winter Garden one of the most desirable cities in Florida. Sit on the front porch and watch as people bike and jog on the famous West Orange Trail, or rent a bike from the corner and join them. The home is close to all major highways.

6–13 Aug

$229 SGD per night

Guest favourite

Home in Clermont

4.93 out of 5 average rating, 187 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow full disinfecting of the house.

30 Aug – 6 Sep

$234 SGD per night

Guest favourite

Guest suite in Oakland

4.81 out of 5 average rating, 42 reviews

Historic, Private Quarters with Kitchenette

Oakland Manor House (OMHouse) is a historic Inn that offers the peace and grace of old Florida. This private rental is near the shores of Lake Apopka in Central Florida, conveniently located to downtown Orlando, Disney and Universal Studios (all within a 20-30 minute drive). The West Orange Trail runs through the quaint town of Oakland to nearby Winter Garden, with its Farmer’s Market, restaurants, brewery, and music venues and to the west, the Oakland Nature Preserve and Clermont.

24–31 Mar

$205 SGD per night

Superhost

Home in Winter Garden

4.88 out of 5 average rating, 17 reviews

Pet Friendly Winter Garden Get-Away near Orlando

Enjoy easy access to everything around Orlando from this perfectly located home base. Disney, Universal, SeaWorld, and more are only a short drive away, and downtown Winter Garden is a gem!✨ This pet-friendly and comfortable studio will be an easy place to rest from all the magic and fun!🪄 Quaint and cozy, we have what matters! A very comfortable new king bed, a great TV and wifi, coffee (or tea - if that's your preference), and endless hot water in the shower!🤗

20–27 Aug

$100 SGD per night

Superhost

Guest suite in Winter Garden

4.82 out of 5 average rating, 285 reviews

Private In-Law Suite Near Disney/Universal/DT

This newly renovated, modern, and clean Mother-in-Law Suite is freshly designed with bright colors and all new furnishings. Everything is thoughtfully selected to create the perfect Airbnb stay. You'll have coffee, decaf, tea, 200mbps Wi-Fi, and high-end mattresses for the perfect night's sleep. You'll stay in the Orlando area, 20min from Disney/Universal/DT Orlando, and minutes from DT Winter Garden, shopping center, & famous 22mile West Orange Bike trail

8–15 Jun

$106 SGD per night

Guest favourite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 788 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. For a video tour type the following link into your browser: https://tinyurl.com/a72vevp5 There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; meemaws-country -cottage which sleeps six.

11–18 Mar

$228 SGD per night

Guest favourite

Guest suite in Clermont

4.83 out of 5 average rating, 126 reviews

Clermont Guest Suite

Apartment with kitchenette that includes microwave, electric skillet, dishwasher and fridge, private bedroom and bathroom in a quiet, established neighborhood close to local attractions. TV with DirecTV. Close to the Disney parks, Universal Studios, Orlando, Tampa and the beaches. The National Training Center for athletes is only a short drive away. Get the convenience of the parks and other attractions with quiet time at the end of the day.

29 Apr – 6 May

$103 SGD per night

Guest favourite

Guest house in Winter Garden

4.94 out of 5 average rating, 48 reviews

Blue Heron Bungalow

The Blue Heron Bungalow is located within walking distance of downtown Winter Garden, where you can find great dining, shops, and entertainment. You can also connect with the West Orange Trail and enjoy 22 miles of walking, running, or biking. If you get adventurous Walt Disney World is less than 30 minutes away, as well as many other attractions. Located in the golf cart district.

12–19 Nov

$140 SGD per night