Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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Top Guest favourite

Home in Winter Garden

4.97 out of 5 average rating, 121 reviews

Experience Downtown Winter Garden, One Block from It All

This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

Top Guest favourite

Apartment in Winter Garden

5 out of 5 average rating, 6 reviews

Winter Garden Charm, Near Disney

2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Garden, this beautifully designed 2-bedroom, 2-bath apartment offers the perfect blend of modern luxury and small-town charm — just 20 minutes from Walt Disney World and Orlando’s top attractions. Located on the iconic Plant Street, you’ll be steps away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

Guest favourite

Home in Winter Garden

4.91 out of 5 average rating, 204 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.

Top Guest favourite

Cottage in Winter Garden

4.99 out of 5 average rating, 155 reviews

The Heart of Winter Garden: Walk to shops & dining

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.

Guest favourite

Townhouse in Clermont

4.91 out of 5 average rating, 235 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!

Guest favourite

Guest suite in Ocoee

4.82 out of 5 average rating, 159 reviews

Charming Studio with Garden (West of Orlando)

We are proud to present a No Smoking on Premises Airbnb. My studio apartment is just the perfect place to hangout. There is a nice fire pit on the back patio and logs to relax with friends and enjoy the warm weather. The black gravel parking space in front is for the use of the Studio guests. The main house guests park in the driveway. We have an onsight massage therapist that can come to your place as an upgrade. Text me for more details. Please NO SMOKING on premises.

Guest favourite

Home in Minneola

4.98 out of 5 average rating, 126 reviews

Cozy Studio Near Disney/Universal/Training center

This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit. Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

Superhost

Guest suite in Orlando

4.74 out of 5 average rating, 818 reviews

Cozy & Private Studio close to the Attractions

Is a small space completely private attached to the side of the house with a separated entrance from the main area. Clean, quite and safe. The studio has a bedroom, a bathroom and there is also an area with microwave, mini fridge, toaster and coffee maker. Wi-fi is available. You’ll be located 17 minutes from Universal Studios and 25 minutes from Disney World driving. Feels free to contact us at any time, we would be happy to help you in any way possible. HABLAMOS ESPAÑOL

Top Guest favourite

Treehouse in St. Cloud

4.96 out of 5 average rating, 982 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. 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; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Top Guest favourite

Apartment in Minneola

4.96 out of 5 average rating, 113 reviews

Spacious Apartment In Minneola

This spacious 1 bedroom / 1 bathroom apartment is located West of Orlando in the beautiful town of Minneola right next to Clermont in the heart of Central Florida and is perfect for a short or long term stay. Features a large bedroom & bathroom, comfortable couch w/ dual recliners, plenty of closet space & storage, and a Smart TV. Kitchen is stocked with all the essentials and has a dishwasher, gas stove, refrigerator w/ ice maker, coffee maker, microwave and crockpot.

Top Guest favourite

Guesthouse in Windermere

4.94 out of 5 average rating, 270 reviews

Paradise nook near Orlando's theme parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

Top Guest favourite

Guest suite in Montverde

4.98 out of 5 average rating, 202 reviews

Green Mountain Getaway (No indoor Smoking or Pets)

(Non Smoker & No Pets) A secluded lot surrounded by FL’s beautiful tropical landscape. Golfer? We are 3 min. from the beautiful Bella Collina's luxury 18 hole golf course, a Nick Faldo design. Also 8 min. from Sanctuary Ridge Golf Club, a more affordable option. Biker? “Killarney Station", is an affordable place to rent bikes or bring your own to ride the beautiful 26 mile trail. 28 minutes to all the attractions!

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Popular amenities for Oakland holiday rentals

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Other great holiday rentals in Oakland

Guest favourite

Private room in Orlando

4.89 out of 5 average rating, 37 reviews

Private Room 2 | Tiny Cottage | 15 min Universal

HannahRating, 5 stars3 months ago

The place was great, just as advertised and in a quiet area. Would recommend having a vehicle if you’re staying here (or anywhere in Orlando really); I took the bus a couple times and it wasn’t too far to walk to the bus stop, but the bus ride is fairly long (though still doable). I had no issues getting in and using the amenities, and my neighbour in the other room was quiet and respectful - good since we share the common space.

Guest favourite

Private room in Metro West

4.95 out of 5 average rating, 65 reviews

Bohemian Oasis w/ Fire Pit Near Universal Studios

JohnRating, 5 stars3 weeks ago

Francellas place was absolutely delightful exactly what my girlfriend and I needed. If I could give her 10 stars I would !!! very friendly amazing host, she definitely should be a Super host and an absolutely cozy and wonderful space she has. I Highly recommend staying here and will definitely come back! outstanding AirBnB and host ! :)

Guest favourite

Private room in Winter Garden

4.9 out of 5 average rating, 239 reviews

20-30 min. Disney, Universal & Downtown Orlando

RichardRating, 5 stars1 week ago

An absolutely amazing place to stay. If you need a room for a couple nights or just one, it is private, easy to access, and in an a beautiful neighborhood.

Guest favourite

Private room in Clermont

4.88 out of 5 average rating, 41 reviews

Private Spacious Room with Pool (The Oasis Room)

CarrollRating, 5 stars3 weeks ago

When an issue arose it was handled effectively. Very clean and nice area. Grest hosts.

Top Guest favourite

Private room in Clermont

4.96 out of 5 average rating, 24 reviews

Boho Loft with Private Entrance

ToniRating, 5 stars4 weeks ago

Squeaky clean loft. No mold or bugs, which I appreciate in a place to stay when traveling to Florida. Everything one would need for a simple stay. Shower super big and fancy. Even a nice little bed-side nightstand with electrical and USB outlet. I stayed to attend a wedding in the area and was also able to get some computer work done, as there was a dinette/table that worked perfect. Also was easily able to connect to my Netflix account on the TV.

Superhost

Private room in Ocoee

4.88 out of 5 average rating, 128 reviews

Cute & cozy 1 bedroom w/ private bath & entrance.

NatashiaRating, 5 stars4 months ago

I enjoyed my stay the area was very nice I chose this location because I had friends and family in the area the Instructions were great I had no issues finding the place my check in and check out went seamlessly this was my first time staying in a room quiet different from what I’m used to but I felt at home and would recommend other nurses/doctors visiting to stay there

Home in Winter Garden

4.82 out of 5 average rating, 22 reviews

Casa aconchegante em Winter Garden

CatherineRating, 5 stars2 weeks ago

Everything about the home was on point and satisfactory. sadly we didn't get to swim at the community pool. The sign at the pool was posted as saying that it closed at dusk, and when we showed up at 7:30 pm on a June evening to swim (an hour before dusk), it was locked and the host at the camp store was not willing to open it for us.

Superhost