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Vacation rentals in Winter Park

Vacation rentals in Winter Park

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winter Park

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

Private En-suite Room #2 at CK Resorts Orlando
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Private En-suite Room #2 at CK Resorts OrlandoCharming 1950's pool and jacuzzi home with mid-century furnishings in living/dining room with original hardwood flooring. Newly remodeled private room in a shared home. Updated shared kitchen with stainless appliances. Guest bedroom is furnished with comfy queen size bed and quality sheets. Room includes a flatscreen TV, desk and internet. Your private bathroom is located in your room. Guests share the living/dining room, kitchen and pool with the home owners Chuck and Ken.

The Little Treehouse 2 at Country Club of Orlando
SUPERHOST
Tiny house · 2 guests · 1 bed · 1 bath

The Little Treehouse 2 at Country Club of OrlandoWith rustic urban charm, The Little Treehouse 2 is a perfect backdrop for your stay in the City Beautiful. This completely renovated 1926 carriage house in the historic Country Club of Orlando 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.

Largest En-Suite Room #1 at CK Resorts Orlando
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Largest En-Suite Room #1 at CK Resorts OrlandoCharming 1950's pool and jacuzzi home with mid-century furnishings in living/dining room with original hardwood flooring. Private room in a shared home. Large updated shared kitchen with travertine floors and stainless appliances. Guest bedroom is furnished with comfy queen bed and hotel quality sheets. Room includes flatscreen TV, table , and internet. A private bath/shower are located in your private room. Guests share the living/dining room, kitchen and pool with the home's owners.

Vacation rentals for every style

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  • Homes
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Popular amenities for Winter Park vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Winter Park

SUPERHOST
  1. Entire apartment
  2. Winter Park
Apt E -Cozy Comfort in the Heart of Winter Park

Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two blocks to the Winter Park Village! Cozy and modern space. Outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's greatest walking communities while residing in style and sophistication. Heated pool and hot tub! The pool, hot tub and grill stations are shared.

$101 per night
SUPERHOST
  1. Entire guesthouse
  2. Orlando
Oasis Garden Cottage -cozy, chic, near everything!

Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

$66 per night
SUPERHOST
  1. Entire guesthouse
  2. Orlando
Treehouse Inn Downtown Orlando, 2 bedrooms 2 bath

Treehouse in Downtown Orlando under a majestic 250 year old heritage Oak tree. Two Brm 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 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.

$101 per night
  1. Entire guest suite
  2. Orlando
Cute 1/1 - Amazing Location Close To Everything!

Private entrance to a quiet one-bedroom guest suite located in the heart of award winning Audubon Park - one of Orlando's most beloved districts! Walk to an abundance of trendy restaurants, coffee shops, a brewery, yoga studio, the popular East End market and a botanical oasis, Leu Gardens. ~7 min drive/Uber to downtown Orlando, Winter Park, Baldwin Park, the Milk District, Ivanhoe Village, Full Sail and Rollins. Less than 30 minutes to Disney, Universal and Orlando International Airport!

$68 per night
SUPERHOST
  1. Entire guesthouse
  2. Orlando
The Loft in College Park

The Loft is a private space located near Downtown Orlando and Ivanhoe Village. It is walking distance to multiple restaurants, bars and shops. Also close to I-4 and easy access to the attractions. The studio space offers a queen size bed as well as a queen size sleeper sofa in the living room area. Luxurious full size bathroom with walk in shower and rain shower head. Perfect get away for those looking to enjoy Orlando!

$65 per night
SUPERHOST
  1. Entire guest suite
  2. Orlando
*Comfortable space(Millenia & International area)*

About: Newly furnished studio size space perfect for a couple or a small sized family! Room includes a queen bed, it’s own bathroom, a stocked kitchen, and a futon that opens up as a sofa bed. All essential appliances and furniture are brand new and operating perfectly! Among them include, a flat screen tv, a micro wave, a mini fridge, kitchen/ bathroom sinks, etc.

$38 per night
SUPERHOST
  1. Entire guest suite
  2. Orlando
Magic space Next to MCO Airport

Welcome to Orlando! This space is perfect for you. You will have your own bathroom, mini kitchen, AC, patio, and prívate entrance. Smoking is no allowed inside but you will have a smoking area. A comfortable and prívate studio; you will feel like home.

$37 per night
SUPERHOST
  1. Private room
  2. Orlando
Private Master Suite in College Park, Orlando FL

Safe, friendly & quiet community just minutes from the highway, theme parks, shopping and dining! Be among the first to experience this newer home! Enjoy a queen bed with premium mattress, WiFi, Roku Smart TV, desk, fridge, coffee machine, and microwave. The bathroom is private and connected to the suite.

$34 per night
SUPERHOST
  1. Private room
  2. Orlando
Tropical King Room ⭐️ Private entrance ⭐️ Pool

Relax in the Modern Tropical King Suite with private entrance from the outside by the pool. The room is closed off from the main house for your privacy. The suite comes with a Plush King size bed, white luxury bedding, attached private travertine stone bath, dual shower heads and 65 inch LED Smart TV W/Netflix, Keurig coffee maker & K cups, small refrigerator with some complimentary beverages stocked, microwave, dishes and utensils, luggage racks, outdoor lounge, Large solar heated swimming pool, pool floats to lounge on, lush landscaped yard, 2 cabana decks W/ hammock under the Palm trees. The Tropical lush landscaped backyard illuminates at night making it the perfect spot to relax and lounge day or night. Uber Eats and other food delivery services that can bring food from local restaurants to your door if you find you just don't want to leave the room.

$69 per night
SUPERHOST
  1. Private room
  2. Orlando
The White and Orange Private Room

A nice Cousy and delicate home, excellent neighborhood, free street parking, a useful family room and backyard for relaxation. The room is clean and nicely decorated {bed spread, clean sheets and towels}.The bathroom is spotless equipped woth personal items {wash soap, toilet paper, and toothpaste}. I guarantee a safe and wonderful stay!

$26 per night
SUPERHOST
  1. Entire guest suite
  2. Orlando
New Apart. near Full Sail, UCF, Parks Attractions.

Relax in this private comfortable one bedroom apartment and 1 bathroom. Comfortable for 2 up to 4 people. With one queen bed and one queen bed sofa. We are conveniently located close to UCF and Full Sail University. Universal Studios only 30 minutes, Walt Disney only 40 minutes, Airport only 20 minutes, Downtown Orlando, Fashion Square Mall, Walmart Supercenter, Sam's Club, Publix, Target, Wawa Gas station, restaurants, and many fast foods.

$60 per night
SUPERHOST
  1. Entire guest suite
  2. Altamonte Springs
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

$68 per night

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