Luxury Hotels in Winter Park

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Sep 8 - Sep 9
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Sep 9 - Sep 10
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Sep 11 - Sep 13
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Sep 18 - Sep 20

Luxury Hotels in Winter Park

The Alfond Inn

The Alfond Inn
Winter Park
  • Poolside bar
  • Concierge services
  • Boutique feel
$245
$306 total
includes taxes & fees
Sep 12 - Sep 13
The Alfond Inn

DoubleTree by Hilton Hotel Orlando Downtown

DoubleTree by Hilton Hotel Orlando Downtown
Ivanhoe Village
  • 24-hour gym
  • Outdoor pool
$111
$125 total
includes taxes & fees
Sep 17 - Sep 18
DoubleTree by Hilton Hotel Orlando Downtown

Hilton Orlando/Altamonte Springs

Hilton Orlando/Altamonte Springs
Altamonte Springs
  • Hot tub
  • Outdoor pool
  • Concierge services
$105
$122 total
includes taxes & fees
Sep 24 - Sep 25
Hilton Orlando/Altamonte Springs

Hotel Beauden, Autograph Collection

Hotel Beauden, Autograph Collection
Downtown Orlando
  • Poolside bar
  • Concierge services
$229
$257 total
includes taxes & fees
Sep 13 - Sep 14
Hotel Beauden, Autograph Collection

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

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
Downtown Orlando
  • Outdoor pool
$113
$405 total
includes taxes & fees
Sep 14 - Sep 15
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Suites by The Wellborn

Suites by The Wellborn
Lake Cherokee
  • Parking available
  • Free WiFi
  • Air conditioning
  • Restaurant
  • Bar
  • Non-smoking
$128
$144 total
includes taxes & fees
Sep 10 - Sep 11
Suites by The Wellborn

The Tiny Cottage in The Springs

The Tiny Cottage in The Springs
Altamonte Springs
  • Free parking
  • Free WiFi
$151
$719 total
includes taxes & fees
Sep 14 - Sep 15
The Tiny Cottage in The Springs

Renaissance Orlando Airport Hotel by Marriott

Renaissance Orlando Airport Hotel by Marriott
Airport North
  • Hot tub
  • Outdoor pool
  • Concierge services
$110
$123 total
includes taxes & fees
Sep 10 - Sep 11
Renaissance Orlando Airport Hotel by Marriott

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport
Orlando
  • 2 restaurants
  • 24-hour gym
  • Outdoor pool
  • Concierge services
$209
$235 total
includes taxes & fees
Sep 14 - Sep 15
Hyatt Regency Orlando International Airport

Marriott Orlando Airport Lakeside

Marriott Orlando Airport Lakeside
Airport North
  • 2 restaurants
  • 24-hour gym
  • Poolside bar
  • Concierge services
$118
$133 total
includes taxes & fees
Sep 22 - Sep 23
Marriott Orlando Airport Lakeside

Rosen Shingle Creek

Rosen Shingle Creek
Orlando
  • 11 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$119
$134 total
includes taxes & fees
Sep 19 - Sep 20
Rosen Shingle Creek

DoubleTree by Hilton Hotel Orlando East - UCF Area

DoubleTree by Hilton Hotel Orlando East - UCF Area
Orlando
  • Outdoor pool
  • Concierge services
$110
$124 total
includes taxes & fees
Sep 15 - Sep 16
DoubleTree by Hilton Hotel Orlando East - UCF Area

The Westin Lake Mary, Orlando North

The Westin Lake Mary, Orlando North
Lake Mary
  • 2 bars
  • Hot tub
  • Outdoor pool
  • Concierge services
$125
$143 total
includes taxes & fees
Sep 9 - Sep 10
The Westin Lake Mary, Orlando North

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Holiday Inn Express & Suites Sanford- Lake Mary by IHG
Sanford
  • 24-hour gym
  • Outdoor pool
$99
$114 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Kirkman North
  • Outdoor pool
$131
$316 total
includes taxes & fees
Sep 14 - Sep 15
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

DoubleTree by Hilton Orlando Theme Park Resort

DoubleTree by Hilton Orlando Theme Park Resort
International Drive District
  • 2 restaurants
  • 24-hour gym
  • Poolside bar
  • Concierge services
$64
$100 total
includes taxes & fees
Sep 25 - Sep 26
DoubleTree by Hilton Orlando Theme Park Resort

Lake Nona Wave Hotel

Lake Nona Wave Hotel
Orlando
  • 3 restaurants
  • 24-hour gym
  • Outdoor pool
  • Concierge services
$217
$246 total
includes taxes & fees
Oct 4 - Oct 5
Lake Nona Wave Hotel

Castle Hotel, Autograph Collection

Castle Hotel, Autograph Collection
International Drive District
  • Hot tub
  • Outdoor pool
$93
$104 total
includes taxes & fees
Sep 13 - Sep 14
Castle Hotel, Autograph Collection

Universal’s Loews Portofino Bay Hotel

Universal’s Loews Portofino Bay Hotel
Florida Center
  • 5 restaurants
  • 3 hot tubs
  • Poolside bar
  • Concierge services
$396
$446 total
includes taxes & fees
Sep 9 - Sep 10
Universal’s Loews Portofino Bay Hotel

Orlando Marriott Lake Mary

Orlando Marriott Lake Mary
Lake Mary
  • 3 restaurants
  • Hot tub
  • Outdoor pool
  • Concierge services
$119
$136 total
includes taxes & fees
Sep 9 - Sep 10
Orlando Marriott Lake Mary
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Top neighborhoods in Winter Park

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.

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.

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.

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.

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.

Top landmarks in Winter Park

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.
Photo by Jay Mullenix

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 traditional brick house with a tiled roof, surrounded by well-maintained hedges and tropical plants.

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 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 Casa Feliz Historic Home Museum, Rollins College, and Winter Park Village.
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A historic building with large columns and moss-covered trees.

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 Red Bug Lake Park, both nearby.
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A sign for the Winter Park Historical Museum at 200 West New England Avenue.

Winter Park History Museum

7.2/10 (5 reviews)
Winter Park History Museum is just one of the attractions in Hannibal Square, 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, Casa Feliz Historic Home Museum, and Orlando Museum of Art.
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A statue of a man in a garden, a yellow building, and a well-maintained lawn.
Photo by Visit Orlando

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, Casa Feliz Historic Home Museum, and Winter Park Village.
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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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