Vacation rentals in Winter Park

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.

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen size. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. This location is 15 min. from downtown, 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals in central Florida, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Perfect home away from home.

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!

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

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 

Apt F -Modern Elegance 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 and grill stations are shared. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload!

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

Adventure by Day. Romance by Night (😊 read the reviews) - Espresso ☕️ - Couple’s Rain Shower - Hammock in Garden - Propane Grill+Utensils - FREE Bikes+Kayaks+Paddle Boards - Smart TV + Streaming - Private Yard Wake up to epic lake views right 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.

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

UPSCALE LOFT SPACE CLOSE TO DOWNTOWN.

Conveniently located between Downtown’s Lake Eola and the foodie-friendly Milk District, this beautifully unique space features an open floor plan with floor to ceiling windows allowing natural light to fill the space. You’re only a short drive to upscale Winter Park restaurants and the vibrant Thornton Park art scene.