Apartments in Winter Park

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Apartments in Winter Park

A residential area with a large pond, houses, and a swimming pool.

A living room with a gray sectional sofa, a patterned ottoman, a dining table with chairs, and a painting of the ocean on the wall.

A modern apartment with a dining area, kitchen, and living space.

A hotel room with a large bed, a wooden dresser, a flat-screen TV, a mirror, and a window with a view of palm trees.

1. Upstay Condo Near MCO Airport w Golf Pool

Ventura

$79

$253 total

includes taxes & fees

Oct 13 - Oct 14

A modern living room with a glass dining table, black upholstered chairs, a black sofa with decorative pillows, and a black and gold patterned rug.

A modern kitchen with white cabinetry, a built-in microwave, a stove, and a refrigerator.

A bedroom with a bed, a ceiling fan, and a bathroom visible in the background.

A balcony with a wooden ceiling, white walls, and a view of a parking area.

2. Sunny Stays

Oak Ridge

$108

$281 total

includes taxes & fees

Sep 26 - Sep 27

A compact bedroom with a bed, a desk, a TV, and a ceiling fan.

A black Keurig coffee maker on a kitchen counter with a white brick backsplash and a small potted plant.

A modern kitchen with white cabinets, a stainless steel refrigerator, a black countertop, a microwave, and an oven.

An outdoor air conditioning unit and a large fan mounted on a building wall.

3. Cozy Modern Studio

Casselberry

$73

$157 total

includes taxes & fees

Sep 29 - Sep 30

A swimming pool with lounge chairs, palm trees, and a building with multiple floors in the background.

A lobby with seating, a television, and a ticket kiosk.

A bar area with a counter and stools, a television, and kitchen appliances.

A bedroom with a bed, a dresser, a TV, and a window with blinds.

4. Modern Condo Near Universal w/ Resort Pool

International Drive District

$56

$152 total

includes taxes & fees

Oct 4 - Oct 5

A modern kitchen with a central island, bar stools, and a dining area with a sofa and table.

A modern interior with white sofas, a round coffee table, and a staircase leading to an upper level.

A modern hotel lobby with a glass staircase, a reception desk, and a view of the outdoors.

A modern kitchen with a central island, bar stools, and a seating area with a sofa and table.

5. Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Downtown Orlando

$104

$396 total

includes taxes & fees

Sep 28 - Sep 29

A modern kitchen with dark wood cabinets, a granite countertop, and a central island. There is a dining area with a table and chairs, and a view of the outside through large windows.

A gym with various exercise equipment, large windows, and a patterned floor.

A modern bathroom with a shower, a sink with a mirror, and a toilet. There are towels hanging on the wall and a plant on the counter.

6. Century Millenia

Florida Center

$129

$220 total

includes taxes & fees

Oct 1 - Oct 2

A modern hotel lobby with a pool table, seating area, and a staircase.

A modern kitchen with a stainless steel sink, a wooden bowl, and a bottle of hand soap.

A multi-story hotel with a swimming pool, outdoor seating, and balconies.

A modern living room with a black sofa, a coffee table, and a kitchen in the background.

7. Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe

International Drive District

$114

$248 total

includes taxes & fees

Sep 28 - Sep 29

A modern living room with a black sofa, a dining table with chairs, a ceiling fan, and a large abstract painting.

A modern living room with a black leather sofa, a round coffee table, and a minimalist white console table.

A modern kitchen with wooden cabinets, a white countertop, a built-in microwave, and two black bar stools.

8. Riviere 2BR Apartment Pet Friendly Oasis Sleeps 6 Close to Epic Universe Pool & Gym

International Drive District

$150

$492 total

includes taxes & fees

Sep 28 - Sep 29

A modern kitchen with a marble countertop, gold faucets, and a large window.

A compact kitchen with a marble backsplash, a gold faucet, a coffee maker, a toaster, and a refrigerator.

A single-story house with a porch, a front door, and a small front yard with plants and a pathway.

A covered patio area with wicker furniture and a clear glass table.

9. Bella Breeze

Downtown Sanford

$77

$153 total

includes taxes & fees

Sep 28 - Sep 29

A hotel room with a ceiling fan, a sofa, a coffee table, a lamp, and a painting on the wall.

A modern kitchen with wooden cabinets, a glass dining table, and a pendant light.

10. Poolside Bliss & Theme Park Thrills: Orlando Oasis

International Drive District

$108

$397 total

includes taxes & fees

Sep 25 - Sep 26

A dining room with a round wooden table set for six, surrounded by wooden chairs. A chandelier hangs from the ceiling, and a wooden cabinet with glass doors is to the right.

A living room with a sofa, armchairs, a TV on a stand, and a ceiling fan.

A golf course with a pond, palm trees, and a well-maintained lawn.

An aerial view of a residential area with multiple tennis courts, a playground, and a golf course.

11. Upstay 2BR Golfer s Retreat w Patio Ventura Resort

Ventura

$83

$246 total

includes taxes & fees

Oct 19 - Oct 20

A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

A hotel room with a bed, a desk, a mirror, a television, and a small table with decorative items.

A kitchen with teal walls, a microwave, stainless steel appliances, and purple cabinets.

A room with a red wall, a flat-screen TV mounted on the wall, a table with a lamp, and a chair. There is a plant on the floor and a sign with the text "SANFORD SHORT TERM SINCE 2021".

12. Boho Nights

Downtown Sanford

$72

$148 total

includes taxes & fees

Sep 27 - Sep 28

A courtyard with a central pathway, surrounded by palm trees and various plants, leading to a building with multiple balconies.

A bar area with a tiled floor, a counter with a menu, and a view of the outside.

A modern living room with a flat-screen TV, a sofa, a coffee table, and a chair.

A modern living room with a leather sofa, a wooden coffee table, and a TV stand with a cityscape painting.

13. 12538 International Drive #c303 Orlando, 2bed

International Drive District

$129

$463 total

includes taxes & fees

Sep 28 - Sep 29

A spacious living room with a beige sofa, a television, and a balcony with a view of the outdoors.

A bedroom with a large bed, two dressers, a ceiling fan, and a door leading to another room.

A dining room with a round wooden table set for six, surrounded by wooden chairs.

14. Upstay Golfer's Retreat w Patio at Ventura Resort

Ventura

$85

$241 total

includes taxes & fees

Oct 19 - Oct 20

A modern living room with a grey sofa, two armchairs, a coffee table, and a small side table with a lamp. There is a brick fireplace, a kitchen area with a countertop and cabinets, and a large window with blinds.

A living room with a fireplace, a TV mounted on the wall, a kitchen area, and a dining table.

A kitchen with a brick wall, white cabinets, and a window overlooking a balcony.

A covered porch with wooden flooring, wicker furniture, and a view of a residential street.

15. The Front Porch

Downtown Sanford

$126

$225 total

includes taxes & fees

Sep 25 - Sep 26

A backyard with a hammock, outdoor seating, and a hot tub.

A modern kitchen with a central island, stainless steel appliances, and orange stools.

A modern kitchen with white cabinets, a built-in oven, and a coffee machine. There is a dining area with a table and chairs, and a living room with a sofa and a TV mounted on the wall.

A modern living room with a geometric-patterned wall, a grey sofa with colorful cushions, a round coffee table, and a brick accent wall.

16. The Contemporary

Downtown Sanford

$126

$283 total

includes taxes & fees

Sep 27 - Sep 28

A spacious living room with a large sofa, a coffee table, and a dining area with chairs and a table.

A swimming pool with lounge chairs, surrounded by trees and buildings.

A building with a white facade, blue doors, and a covered patio area with outdoor seating.

A spacious lobby with a reception desk, seating area, and a modern kitchen visible in the background.

17. Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Kirkman North

$114

$297 total

includes taxes & fees

Sep 28 - Sep 29

A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

A porch with two rocking chairs and a window.

A blue house with a porch, a front door, and a small garden area.

A kitchen with wooden shelves holding glassware, a coffee maker, and a sign reading "THE BLUE AZTEC".

18. The Blue Aztec

Downtown Sanford

$77

$228 total

includes taxes & fees

Sep 28 - Sep 29

A compact kitchen with a built-in sink, a countertop, and a grey cabinet. There is a sofa with a cushion and a small table in the adjacent living area.

A bedroom with a bed, curtains, a nightstand, and wall art.

A bathroom with a white toilet, a white sink, and a shower curtain.

A kitchen with a coffee maker, a pot on the stove, and a plant on a shelf.

19. The Mellow Yellow

Downtown Sanford

$75

$226 total

includes taxes & fees

Sep 27 - Sep 28

A backyard with a hammock, outdoor seating, and string lights.

A kitchen with wooden beams, a TV, and a mural with musical notes.

A modern kitchen with a flat-screen TV, wooden bar stools, a dining table, and a colorful mural on the wall.

A modern interior with a staircase, a brick wall, a mural, and a desk area.

20. The Jazz Loft

Downtown Sanford

$72

$148 total

includes taxes & fees

Oct 1 - Oct 2

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Top neighborhoods in Winter Park

A sign for the Winter Park Historical Museum at 200 West New England Avenue.

A brick building with a wooden fence, a bench, and a sign for the Winter Park Historical Museum.

A sign for the Winter Park Historical Museum with three black lamps on top.

A brick building with a black door, a poster of a vintage car, and a bench.

A brick building with a sign reading "Winter Park Historical Museum".

Hannibal Square

Hannibal Square blends rich African American heritage with modern charm in Winter Park's cultural heart. The Heritage Center showcases local Black history through exhibits and art, while New England Avenue buzzes with boutique galleries and upscale restaurants in restored buildings. History buffs and art lovers can explore the neighborhood's preserved architecture and cultural landmarks. The dining scene features Southern fusion and contemporary American cuisine in historic settings with tree-lined outdoor seating. Most accommodations are charming boutique bed & breakfasts in converted historic homes. The compact, walkable layout makes exploring this authentic cultural enclave a breeze.

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A park with a central fountain, surrounded by benches and trees.

A covered patio with wicker furniture and large windows overlooking a garden.

A museum interior with a central stained glass window, wooden benches, potted plants, and framed artworks on the walls.

A museum interior with classical sculptures and framed paintings on the walls.

A display of various vases on a shelf in a museum.

Park Avenue District

Park Avenue District combines elegant shopping with cultural treasures in Winter Park's sophisticated heart. The Charles Hosmer Morse Museum dazzles with its Tiffany glass collection while tree-lined boulevards showcase Mediterranean Revival architecture. Stroll through Central Park's gardens between boutique visits or enjoy sidewalk cafés, galleries, and shops in this European-inspired atmosphere. Fine dining dominates with farm-to-table restaurants and wine bars offering seasonal cuisine. Most attractions sit within a 3-block radius, making this walkable district ideal for architecture enthusiasts. Boutique hotels and luxury bed & breakfasts provide upscale accommodations with personalized service throughout this refined neighborhood.

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A wooden boardwalk leading to a gazebo over water.

A colorful hot air balloon with a striped pattern, a checkered pattern, and a bear-shaped balloon nearby.

Baldwin Park

Baldwin Park offers a peaceful retreat from Orlando's tourist hustle with its scenic Lake Baldwin at the center of it all. Tree-lined streets wind through this charming planned community where wooden boardwalks and fishing piers dot the lakeside trail. Pocket parks and playgrounds provide perfect spots for afternoon breaks, while the Village Center buzzes with boutique shopping and casual dining. The neighborhood shines with its walkable layout and extensive trail system, making cars optional for local exploration. Upscale cafes and bistros serve everything from Italian to American fare, while vacation rentals and condos offer homey alternatives to Orlando's mega-resorts. Getting to theme parks requires a short drive, but that's the trade-off for genuine tranquility.

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A house covered in lights and decorations, with a sign that reads "Santa's Workshop."

Goldenrod

Goldenrod offers a laid-back suburban vibe just outside Orlando's buzzing center. The neighborhood blends residential calm with convenient access to attractions, making it perfect for travelers who want breathing room. You can hit the lanes at Aloma Bowl, tee off at Winter Pines Golf Club, or explore nearby Red Bug Lake Park between Orlando adventures. Budget-friendly dining spots line Semoran Boulevard with casual chain restaurants and family diners serving meals that won't break the bank. The area is definitely car country, so rent wheels to zip between Winter Park Village and downtown Orlando. Extended-stay hotels and mid-range chains provide comfy, no-fuss places to crash after long theme park days.

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A park with a central fountain, surrounded by trees and benches.

College Quarter

College Quarter wraps you in academic charm with Mediterranean Revival buildings and leafy walkways. Students chat at outdoor cafes while indie bookstores and small galleries invite exploration. Stroll through palm-dotted streets where historic architecture creates a scholarly yet welcoming vibe. Catch a game at Barker Stadium or visit the Winter Park Playhouse for a cultural fix. Budget-friendly cafes and casual eateries cater to student appetites with extended hours during the school year. Vacation rentals in converted student housing offer affordable stays, putting you steps away from campus attractions. The neighborhood's walkable streets make getting around a breeze without needing a car.

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Top landmarks in Winter Park

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.

Full Sail University

8.4/10 (73 reviews)

If you'd like to get a taste of Winter Park student life, check out Full Sail University, located 2.2 mi (3.6 km) from central Winter Park.

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A historic building with a tiled roof and arched windows, surrounded by lush greenery and a brick pathway.

Casa Feliz Historic Home Museum

9.2/10 (34 reviews)

If museums are on your list of things to see in Winter Park, then you might want to head to Casa Feliz Historic Home Museum. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you want to see more of the museums in Winter Park, you can easily walk to Morse Museum of American Art or Winter Park History Museum.

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A swampy area with large, moss-covered tree stumps in the water.

Kraft Azalea Gardens

9.6/10 (24 reviews)

Ready for an education in local botany? Kraft Azalea Gardens should make your list of places to visit, located 0.8 mi (1.3 km) from central Winter Park. Want to stretch your legs some more? Head to Harry P. Leu Gardens and Festival Park, both nearby.

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A fountain with water spouting from its top, surrounded by a circular pool.

Winter Park Country Club

9.4/10 (3 reviews)

You might want to practice your swing at Winter Park Country Club, a golf course located 0.6 mi (0.9 km) from central Winter Park. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If Winter Park Country Club doesn't quite scratch your golfing itch, Dubsdread Golf Course, and Casselberry Golf Club are also nearby.

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A statue of a man in a garden, a yellow building, and a well-maintained lawn.

Albin Polasek Museum and Sculpture Gardens

8.8/10 (26 reviews)

Albin Polasek Museum and Sculpture Gardens is 0.4 mi (0.6 km) from central Winter Park, why not stop by during your stay. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you want to experience more of the culture Winter Park has to offer, head to Rollins College, Winter Park Village, and Harry P. Leu Gardens.

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A stained glass window with a mermaid design.

Morse Museum of American Art

9.8/10 (68 reviews)

Morse Museum of American Art is just one of the attractions in Park Avenue District, Winter Park so you might want to stop by during your trip. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you want to experience more of the culture Winter Park has to offer, head to Rollins College, Winter Park Village, and Orlando Museum of Art.

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Winter Park Village

9.6/10 (323 reviews)

If you like shopping, take time out to go to Winter Park Village when in Winter Park. It's also full of great shops and restaurants, so you can spend the afternoon having a wander.

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Lee Road Shopping Center

9.0/10 (38 reviews)

If you want to give your credit card some exercise, head out to Lee Road Shopping Center in Fairview Shores. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. Splash some more cash at The Center of Winter Park Shopping Center and Hollie Anna Shopping Center.

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Learn more about Winter Park

Escape the theme park frenzy on Park Avenue's brick-paved elegance, where upscale boutiques and outdoor cafes create a sophisticated small-town atmosphere. The Morse Museum houses an unrivaled collection of Tiffany glass that sparkles like frozen sunlight. Paddle a swan boat across Lake Osceola for postcard-worthy photos, or explore the hidden beauty of Kraft Azalea Gardens. Rollins College campus offers Spanish Mediterranean architecture worth admiring before browsing the Albin Polasek Museum's sculpture gardens. Winter Park Village provides shopping without the mall madness, while Casa Feliz Historic Home Museum reveals the city's wealthy winter resident past. Visit during a festival when the already-charming streets transform into celebration central.

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A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.

Find out more about Winter Park

If you're looking to discover somewhere new, look no further than Winter Park. Whether you're planning to stay for a night or for the week, the area around Winter Park has accommodations to fit every need. Search for hotels in Winter Park with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Winter Park hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Winter Park hotel deals are here with our lowest price guarantee.