Vacation rentals in Lake Osceola

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Top-rated vacation rentals in Lake Osceola

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Guest favorite

Apartment in Winter Park

4.95 out of 5 average rating, 282 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.

Feb 20 – 27

R2,174 ZAR per night

Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 300 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

May 11 – 18

R1,441 ZAR per night

Guest favorite

Bungalow in Winter Park

4.98 out of 5 average rating, 231 reviews

Cozy 2/2 Bungalow - Downtown Winterpark/Orlando

Your family will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, you will be 5 minutes from Downtown Orlando and Downtown Edgewater, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! College Park local parks and golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music

Sep 4 – 11

R2,656 ZAR per night

Guest favorite

Bungalow in Maitland

4.86 out of 5 average rating, 487 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Sep 20 – 27

R1,747 ZAR per night

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 315 reviews

St. Augustine suite

Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

Jun 14 – 21

R1,701 ZAR per night

Guest favorite

Apartment in Winter Park

4.96 out of 5 average rating, 196 reviews

Apt C -Modern Elegance in the Heart of Winter Park

Light, bright and full of delight! Fastest internet speed available: 154MBPS download and 20 MBPS upload! Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Heated pool and hot tub, poolside grill and bikes for your enjoyment! Three blocks to Park Ave and two blocks to the Winter Park Village! Simple elegance downtown defined by contemporary design and leisurely living. Enjoy the convenience and tranquility of one of Florida's best walking communities

Apr 26 – May 3

R2,114 ZAR per night

Guest favorite

Home in Maitland

4.96 out of 5 average rating, 113 reviews

The Butterfly Bungalow near Park Ave

This 1950s bungalow has been lovingly restored to maintain it's Florida charm and offer simple comforts. Located in a family-friendly neighborhood just a few blocks from the Enzian Theater, the bungalow is close to restaurants and shops lining the cobblestone streets of Park Ave, and centrally located to historic areas of both Winter Park and Maitland. Park Ave shopping district - 1.5 miles Whole Foods - 0.8 miles Publix - 0.8 miles SunRail - 1.7 miles Downtown Orlando - 8 miles

Jan 4 – 11

R2,544 ZAR per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 634 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.

Sep 27 – Oct 4

R2,417 ZAR per night

Guest favorite

Yurt in Orlando

4.96 out of 5 average rating, 217 reviews

Lakefront Yurt King Bed *A/C* Kayaks, Bikes

The Orlando Yurt Experience for Adults Only. Imagine Laying in Bed, Just Feet From the Water. Watching the Sunset or Looking Up at the Stars... ★★★★★ "It was the most peaceful, serene and gorgeous space. It was a breathtaking experience." Zonnetta Marie - April 2023 400sf Yurt with Huge King Bed & Private Lakeside Deck. Private Outdoor Bathroom & Shower for Two. Indoor & Outdoor Dining Areas. Alexa Controlled Heat & A/C. Free Unlimited Use of Kayaks & Bicycles.

May 5 – 12

R2,163 ZAR per night

Superhost

Apartment in Maitland

4.82 out of 5 average rating, 250 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.

Sep 28 – Oct 5

R1,361 ZAR per night

Guest favorite

Home in Winter Park

4.9 out of 5 average rating, 129 reviews

Guest Suite in Winter Park/Orlando

This private guest suite is connected to our home but completely exclusive with a separate entrance, private bathroom and no access to the main house. The layout is like a studio apartment with a bedroom, dining area and kitchenette. Outside there is also a patio area for guests. Full Sail University- 5 min University of Central Florida- 15 min Orlando International Airport- 25 min Universal Studios- 25 min Disney World- 30 min

May 10 – 17

R1,468 ZAR per night

Guest favorite

Guesthouse in Maitland

4.87 out of 5 average rating, 381 reviews

Chez Bienvenu

Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space

Aug 6 – 13

R1,990 ZAR per night