Apartment holiday rentals in Winter Park

5 out of 5 average rating, 23 reviews

• The Catherine • 1 mile to downtown | 2 King beds

The Catherine is a chic, two-bedroom apartment that combines the best of downtown energy with the peace of a quiet neighborhood. We are located just minutes from Orlando’s vibrant city life in a walkable neighborhood with parks, cafes, cobblestone paved streets, and oversized oak trees dripping with Spanish moss. You'll find unique touches like a rose gold disco ball, a vintage record music station where you can browse a curated selection of vinyl classics, two king beds, and a chef's kitchen.

4.94 out of 5 average rating, 218 reviews

Flat in College Park

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft apartment - queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. No cleaning fee $20 pet fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 2 m

4.99 out of 5 average rating, 166 reviews

Parent's Retreat!

Whether working in the area, visiting your student or catching a UCF Sporting event. This pet friendly "Parent's Retreat" is just what you're looking for. Located less than 2 miles from campus. this apartment is a great place to land at the end of the day. Kitchen includes microwave, fridge, coffee maker and air fryer. This 380 sq ft newly remodeled mother-in-law suite has private entrance, patio and yard. Suite is completely closed off from the house and has keyless locks for easy check in.

Flat in Altamonte Springs

4.96 out of 5 average rating, 329 reviews

St.John suite

Luxurious space with PRIVATE ENTRANCE, 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 lined streets, Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting.

4.89 out of 5 average rating, 161 reviews

Flat 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.

4.95 out of 5 average rating, 111 reviews

Cozy Private Apartment - Stylish & Spotless

Completely private guests apartment with bedroom,bathroom, living room, kitchen, private entrance and private fenced patio **NO SHARING AREAS.** Guests will enjoy easy access to everything from this centrally located place ; We’re within minutes to major shopping mall Waterford Lakes Town Center; with an array of restaurants within proximity to major highways for easy access to all the theme parks Disney World, Universal Sea World. Enjoy the tranquility of our neighborhood.

Superhost

4.81 out of 5 average rating, 353 reviews

✪ Fashionable ✔Location ✔Netflix ✔Parking ✔Wifi

You also will have ✔FREE parking ✔wifi ✔ Netflix. All at an unbeatable price. Classy, clean and crisp modern decor. Bright white and gray fabrics, with warm golden metal accents. Snug and personal with stylish interior decor, you won't want to leave! Excellent location, 15 minutes from downtown Orlando, Amway Center, Winter Park, UCF and the airport. The theme parks are just less than 30 mins away too. Ideal for small groups, business travel, and traveling with children.

4.81 out of 5 average rating, 27 reviews

Flat in Eatonville

Cozy Town Suites B

Chris & Tish Suites: We have a partnership with traveling nurses and doctors. We are LESS than 2 minutes to get to the interstate-making it a breeze to get to and from the hospital. A super cozy and quiet apartment ALL to yourself! ( 1 bedroom with queen size bed and a shower). 26 minutes from DISNEY WORLD! This is the perfect central location. Less than 1 minute from Winter Park. Very quiet, newly renovated home in a Historic Town. Warm Regards, Chris & Tish

4.94 out of 5 average rating, 115 reviews

Spacious DT Orlando house off Lake Eola/ sleeps 6

Nestled in the historic Lake Eola Heights neighborhood and centrally located a block from Lake Eola Park. Close to bars and restaurants, and only a 20 min drive to MCO & all major theme parks. Space was designed with luxury appointments, for the upscale traveler to be comfortable as well as someone seeking accommodations with better offerings than that of what hotels have to offer. With 2 King beds in the bedrooms our space is big enough to fit your entire group.

4.9 out of 5 average rating, 271 reviews

Flat in Orange County

Lake Nona / Comfy Corner

We have a very comfortable place , centric location , close to any activity or necessity for our guests. One but not least, USTA Tennis Campus , DisneWorld, Universal Studios, Sea World, Aquatica, Children Hospital,Veteran Hospital, Restaurants, Parks, Theme Parks, Waterparks, MCO International Airport only 10 min Downtown Orlando, Florida Mall, last but not least Millennium Mall, Cocoa Beach, Tampa, Kennedy Space Center and way more! Just a drive away.,

4.89 out of 5 average rating, 179 reviews

2/2 PentHouse Downtown Orlando

This fully furnished 2/2 Penthouse, comes fully equipped with all the necessities you need for your vacation or short stay to Orlando, The City Beautiful. We have fully remodeled our house and would like to share the experience with you. The bedrooms come with King beds. Our kitchen comes with pots, pans, plates and silverware, and has a FREE Nespresso for your morning wake up! We have our laundry machines in-house and yes, you can use them.