Holiday rentals in Orlando

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Top-rated holiday rentals in Orlando

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Guest favourite

Flat in Winter Park

4.95 out of 5 average rating, 283 reviews

Get a Little Glam in a Retro Palm Beach-Style Boudoir

The whole upstairs portion of the building is all yours. Location is prime as it is close to all things wonderful in Winter Park FL. Two streets behind is Lake Killarney. The space is beautifully decorated and offers guests a charming get away. Please note: It is a 13.6 mile drive (21 - 40 minutes depending on traffic) from Universal Studio's and a 21.7mile drive (24 - 45 minutes depending on traffic) to Disney World. There is a lock box located under the stairwell on the left side of the building. I will message you with your code for access. Once you get your key, head on up the stairs and enjoy your home away from home. Welcome! I live 3 minutes away from the Air BnB property and I work in the downstairs portion of the building, so I am local and available to assist with any additional requests. Message me anytime! Or text 407 575 3502 The Fairbanks corridor of Winter Park is the main artery to affluent areas, offering great shopping and dining close by. This hidden gem is a short walk to grocery stores, restaurants, and Winter Park Village shopping district with its movie theater. Light sleepers, please be aware that there is the potential for traffic noise. The BnB offers a large parking lot. You should have no problem at all if you desire to arrive by car. The area is also safe to bike around and Uber or Lyft operates in the area. No smoking please.

6–13 Mar

$156 SGD per night

Guest favourite

Guest house in Orlando

5.0 out of 5 average rating, 162 reviews

Treehouse Inn Downtown Orlando, 2 bedrooms 2 bath

Treehouse in Downtown Orlando is surrounded by majestic heritage Oaks. Two Bed Two Bath with a Mini-Master & full Kitchen. Very private deck near Bamboo Hedge. Two blocks from a small neighborhood Deli serving breakfast, lunch and dinner with Great coffee & Craft beers. We are walking distance from popular Thornton Park pubs and restaurants. Lake Greenwood and Lake Davis are close by for a leisurely walk or brisk jog. Enhanced cleaning in use. Jakob and Marty are happy to help with your stay.

2–9 Jul

$164 SGD per night

Guest favourite

Loft in Orlando

4.94 out of 5 average rating, 461 reviews

Contemporary Loft Near Downtown

Conveniently located between the foodie-friendly Milk District and The City Beautiful’s Downtown, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is a 20 minute drive, Disney is 35 min., MCO 20 minutes

19–26 Aug

$203 SGD per night

Guest favourite

Guest suite in Orlando

4.99 out of 5 average rating, 124 reviews

Beautiful studio with pool & close to attractions!

An amazing studio space, attached to the main home, with private entrance, King size bed, full bath, and kitchenette. Recently renovated and very comfortable. New Mitsubishi mini-split AC system and a Nespresso Machine for your morning coffee. Access to pool area, gazebo, and washer/dryer outside! Centrally located: under 20 minutes to the airport, 5 minutes to Florida Mall, 10 minutes to Mall at Millenia, under 20 minutes to Universal Studios, 35 minutes to Disney, and 10 minutes to Downtown!

5–12 Sep

$113 SGD per night

Guest favourite

Guest suite in Orlando

4.98 out of 5 average rating, 303 reviews

A SUITE RETREAT with a Garden View in the City

A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

20–27 Apr

$109 SGD per night

Guest favourite

Guest house in East Central Park

5.0 out of 5 average rating, 154 reviews

The Sacred Space Downtown Orlando Milk District

This delightful hideaway embodies brightness, cleanliness, and a fragrance-free environment. Enjoy a tranquil stay with hypoallergenic bedding and experience unmatched comfort on a luxurious purple mattress for rejuvenating sleep. Conveniently located near Lake Eola, lively bars, and an abundance of dining options, this private sanctuary provides the perfect balance of convenience and serenity. Amidst the bustling surroundings, our tranquil retreat remains tucked away, offering a peaceful stay.

22–29 Aug

$150 SGD per night

Guest favourite

Guest house in Orlando

4.88 out of 5 average rating, 218 reviews

Couples Oasis *Heated Pool* and Lake View

Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $10 every extra day.

13–20 Sep

$171 SGD per night

Guest favourite

Tiny home in Orlando

4.98 out of 5 average rating, 639 reviews

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

6–13 Dec

$162 SGD per night

Guest favourite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 790 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.

21–28 Apr

$229 SGD per night

Superhost

Flat in Maitland

4.81 out of 5 average rating, 263 reviews

At Mine | Elegant Double Suite in North Orlando

Experience ultimate comfort at our Maitland, FL hotel, ideally located just north of Downtown Orlando. we're the area's largest hotel. Enjoy the convenience and luxury of plush bedding, modern furnishings, and upscale Grohe showers in your room. Relax by our outdoor pool, keep fit in the 24-hour gym, and access the Genesis Health Club. With over 15,000 square feet of event space, secure parking, and free Wi-Fi, we've got you covered.

26 Aug – 2 Sep

$89 SGD per night

Guest favourite

Guest house in Orlando

4.95 out of 5 average rating, 132 reviews

Jefferson St. Cottage

This cottage is a unique free-standing detached dwelling in the heart of Lawsona Park (Historic Downtown Orlando). It sits behind the owner's main house in the back of the lot. The cottage is newly updated with all the amenities to give guests a perfect secluded area near bars, eateries, parks as well as easy access to highways to visit Universal, Disney World, Sea World any more attractions in central Florida.

24–31 Jul

$128 SGD per night

Guest favourite

Guest suite in Orlando

4.97 out of 5 average rating, 384 reviews

Vacation & Oasis Mood with #1 location - Pool

From our family to you, we are welcoming you in our Home into our private Orlando, Florida, Oasis :-) Located a very short commute to some of the world most famous tourist attraction, Disney & Universal studio to the privacy of our fully equipped Guest area. We want to make sure that your stay to our home will be memorable and we want to see you again :-)

17–24 Aug

$156 SGD per night