Vacation rentals in Winter Park

4.84 out of 5 average rating, 305 reviews

Tiny home in Orlando

The Blue Heron 6 Month Lakefront Tiny House Rental

The Blue Heron was the 8th tiny home to join our community in Orlando, Florida in 2018. You'll find this inviting accommodation steps from Lake Fairview and it can accommodate up to 4 guests. There is a queen-size bed in the lofted bedroom, in addition to a sofa bed in the living room area. A fully equipped kitchen and modern bathroom will keep you feeling at home, but you’ll likely want to spend the majority of your stay on the wide, wooden deck relaxing and enjoying the scenery. During your stay, take advantage of Florida lake life! We encourage all guests to take advantage our FREE kayaks and paddle board rentals as well as our yard games, hammocks, fire pit, propane grill, volleyball, cornhole and fishing gear upon request. Turn your tiny home experience into big fun on the lake! **This tiny house is not pet friendly**

4.99 out of 5 average rating, 133 reviews

Home in Winter Park

Stylish newly updated home in Winter Park

Sleeps 8 people comfortably but can fit 10. This home has VERY CONVENIENT ACCESS TO I-4 making it easy to get to Orlando's most sought after attractions, including Park Avenue, Downtown Orlando, Rollins College, Leu Gardens, Mills Ave, Baldwin Park, College Park, Camping World Stadium, Amway Arena, SunRail, and many hospitals. SHORT WALK to 3 notable restaurants Also nearby: Universal Studios (20 min) Outlet Mall (20 min) International Drive (25 min) Orlando Airport (30 min) Disney (~30-40 min)

4.88 out of 5 average rating, 561 reviews

Bungalow in Maitland

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.

4.9 out of 5 average rating, 143 reviews

Apartment in Winter Park

The Lake House

Welcome to the mid-century Lake House. 370 square feet apartment with a private entrance and original terrazzo floors. Located on a quiet residential street on a small lake, and located within a 5-minute drive to anything you may need! Starbucks and Panera are within walking distance, and dozens of other places to eat. Publix, Walgreens, and Sprouts are just around the corner. A short 10 minute drive to the famous Park Ave, in Downtown Winter Park with shopping and gourmet restaurants.

4.97 out of 5 average rating, 317 reviews

Bungalow in College Park

Cozy 2/2 Home - Downtown Winterpark/Orlando

You will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, 5 minutes from Advent Health Hospital, you will be 5 minutes from Downtown Orlando an, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! Dubsdread 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

Guest suite in College Park

4.96 out of 5 average rating, 189 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

4.99 out of 5 average rating, 122 reviews

Guesthouse in Orlando

Baldwin Park Guest House

Welcome to Beautiful Baldwin Park, This Brand New Private sanctuary with modern day decorations, amenities and large screen television is the perfect place for a couple or single to experience the beautiful Orlando area. Conveniently located near the Orlando International Airport, Winter Park and downtown area Enjoy your morning coffee on the private patio . This entire property is very clean and well maintained, we look forward to being your host for your next central Florida visit

4.98 out of 5 average rating, 104 reviews

Bungalow in College Park

Cozy Cottage in College Park.

Whether you're coming to Orlando for adventure at one of the many theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden in College Park, located in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

Tiny home in Baldwin Park

4.96 out of 5 average rating, 289 reviews

Lake View from King Bed+Free Bikes+Kayaks+Espresso

The Perfect Couple’s Getaway❤️ (😊 read the reviews) - Espresso ☕️ - Couple’s Rain Shower -Beautiful View of Lake from Bed - Hammock in Garden - Propane Grill+Utensils - FREE Bikes+Kayaks+Paddle Boards - Smart TV + Streaming - Private Garden Yard with Seating Wake up to epic lake views from your king bed. Sip strong Cuban espresso, then launch a kayak or paddle board into calm waters—or bike into one of three charming nearby towns: Winter Park, Baldwin Park, or Downtown Orlando.

4.75 out of 5 average rating, 488 reviews

Guesthouse in Orlando

Private Cozy Cottage in heart of Orlando

Come stay at our Cozy quaint suite located in the historic downtown Lake Davis neighborhood with a 5 minute walk to a quiet neighborhood market, 1 mile walk to downtown Orlando with entertainment and the Downtown Farmers Market. Less than 30 minutes to the worlds greatest attractions Disney, Universal Studios, Sea World etc. The beach is a 1 hour drive. One car parking. The room is connected to a family home you’re able to hear guest next door. Not for parties . Please NO pets.

4.97 out of 5 average rating, 764 reviews

Tiny home in Spring Lake

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.

4.96 out of 5 average rating, 214 reviews

Apartment in Winter Park

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 , 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

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Winter Park vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Winter Park's top sights

Orlando Science Center124 locals recommend

Orlando Museum of Art58 locals recommend

Harry P. Leu Gardens83 locals recommend

Other great vacation rentals in Winter Park

4.83 out of 5 average rating, 99 reviews

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

CindyRating, 5 stars2 days ago

Property was just as described. Very easy communication with the owner. We were very comfortable there and enjoyed our time. Very handy location. Would definitely stay there again. Thank you for hosting us.

4.93 out of 5 average rating, 72 reviews

Home in Winter Park

Winter Park Guest Suite near UCF/FullSail/Rollins!

PaulinaRating, 5 stars6 days ago

Grear stay!!! We were extremely surprised when we walked in the door. It was exactly as the photographs. The airbnb was very clean. We did encounter a few flies in the airbnb but my son was able to get rid of them. I texted the hosts and they responded right away. They were apologetic and assured me that it had never happened before and would look into it. The very next day, they sent someone to try to figure out the problem. I believe it was because the garbage bin was next to the airbnb. Once it was moved over to the other side, we did not experience anymore flies. The airbnb was closed to Full Sail University, where my son did a one week summer program. It was also very close to grocery stores and restaurants. I was able to buy groceries and at times get them delivered. I was able to cook in there two range burner which was my number one reason for staying at an airbnb instead of a hotel. The airb had the pots, pans, and dishes. I did not rent a car and the Uber service was great.

5 out of 5 average rating, 53 reviews

Home in Baldwin Park

SEEN ON TV! Private Resort, Nintendo-theme Game Rm

RichardRating, 5 stars3 weeks ago

Caitlin was incredibly responsive whenever we had a question about anything. The house was incredible, they took so much time and money making all the amenities and details first class. Everything was explained in easy to read pamphlets that described everything. The game room was a big hit, and of course the bbq and pool area, and my family absolutely loved it. Everyone was raving at how nice a place the house was. I highly recommend staying here if you can, I would definitely rent again if we’re ever back in the area.

4.85 out of 5 average rating, 54 reviews

Home in Winter Park

NEW! ☀Bungalow+Patio+FirePit! Close to Everything!

DebbieRating, 5 stars2 weeks ago

Overall our stay was great! The only snag was the place hadn’t been cleaned when we arrived due to a booking/communication error. Greg immediately responded and had cleaners there within the hour. Once It was cleaned the place was immaculate and our stay was peaceful - exactly what we were looking for!

4.98 out of 5 average rating, 45 reviews

Home in Orlando

Charming Bungalow in Winter Park

TaralynnRating, 5 stars1 week ago

Loved the stay at this place! The instructions were clear on how to get to the parking and the large kitchen island was a great gathering spot. This house had more than enough space for what our needs were. Host was very responsive. Thank you for having us!

Guesthouse in College Park

4.98 out of 5 average rating, 83 reviews

Amazing New Pool House!

LeonRating, 5 stars3 days ago

We had an excellent stay in David and Nadia's pool house. Nadia was very responsive, friendly, and proactive host and made sure our visit went smoothly. The place matched the photos and description perfectly -- it's a real gem! The pool house itself is modern, attractive, and comfortable with everything you need for a comfortable stay. The shared backyard is such a lovely place to spend time. We especially enjoyed the pool and putting green. Overall we had a great trip and would happily stay there again.

4.72 out of 5 average rating, 39 reviews

Home in Baldwin Park

Walk To Bike Trail, Baldwin Lake

CynthiaRating, 5 stars5 months ago

We had a very comfortable stay. Michelle’s has a charming place close to a lovely park where we took several walks. Also the restaurants in the area are very good.