Best Date Night Restaurants in Maitland

52 restaurants available nearby

1. Jazz Tastings

4.8

Exceptional(590)

Price: Expensive

• American • Maitland

Booked 17 times today

• $10 Entertainment Fee Per Person on Friday, Saturday & Monday Night Jazz Jam (first Monday of the month)• • $25 Minimum Food & Beverage Purchase Per Person Monday-Thursday•• $50 Minimum Food & Beverage Purchase Per Person for on Friday & Saturday•• Friday & Saturday: Reservations available until 7:30pm, after that time we accept walk ins only!••Parties of 7 or more must purchase a group package, contact us at 407-795-1582•**If minimums are not met you will be charged the remaining balance**Weekly Deals:Happy Hour Tuesday-Thursday from 5:30pm-7pm: Half off appetizersTuesday- Burger & Brew $15, 1/2 off Wine Bottles all night!Wednesday- 1/2 off select Whiskey & Wine all night!Thursday- 1/2 off Don Julio Anejo, Blanco and Reposado all night! Located in Maitland, Florida, Jazz Tastings combines the intimate atmosphere of a jazz bar with a classy menu. There is also an impressive alcohol list to enjoy along with the soothing music and great food.

A photo of AVA MediterrAegean restaurant

2. AVA MediterrAegean

4.7

Exceptional(2262)

Price: Expensive

• Mediterranean • Winter Park

Booked 134 times today

AVA MediterrAegean is a modern Greek Agora, a multi-sensory transporting venue bringing dining experience and pleasure together in a refined and spirited atmosphere.Meaning life, water, island, bird in Greek, AVA is a celebration of splendor, freedom, escapism and joy, where genuine hospitality, delectable food and vibrant atmosphere combine to entertain the senses and transport guests to celebrate the night away.Deeply rooted in the Mediterranean, AVA lives by its mantra “PAREA”, from Greek, meaning a group of friends, who gather to share life experiences, philosophies, values and ideas.Lunch | Brunch | Dinner.

A photo of Permanent Vacation restaurant

3. Permanent Vacation

4.9

Exceptional(280)

Price: Moderate

• American • Maitland

Booked 32 times today

Permanent Vacation is a tropical destination with an extensive rum list, rum mixed with exotic flavors, exquisite bites, immersive special effects and vibes that never stray too far from the equator!You must be at least 21 to dine or drink with us.

A photo of AJ CHOCOLATE HOUSE restaurant

4. AJ CHOCOLATE HOUSE

4.5

Awesome(70)

Price: Moderate

• Dessert • Winter Park

Booked 13 times today

Now serving brunch! Every day till 3pmWith over 150 different amazing chocolate delicacies, AJ Chocolate House is truly a place to come unwind and enjoy the sweetest things life has to offer. Whether you want to get together with an old friend to enjoy great chocolates or a slice of delicate cake with a cup of coffee or hot chocolate, bring your other half for a sweet brunch with Brussels waffles or a date with chocolate fondue and a glass of wine, planning a party or an event, or simply need to find the perfect gift for a chocolate lover, as well as if you are shopping for a special occasion or corporate gifts - we are happy to welcome you to our house.

A photo of Fleming's Steakhouse - Winter Park restaurant

5. Fleming's Steakhouse - Winter Park

4.7

Exceptional(2241)

Price: Expensive

• Steak • Winter Park

Booked 50 times today

Your Winter Park Fleming’s is located in Winter Park on the corner of Lee Road and Orlando Avenue. Fleming's in Winter Park is an outstanding choice to enjoy an exceptional Prime steak, glass of wine or handcrafted cocktail in Orlando. Whether you’re celebrating a special occasion, hosting a business dinner or simply wanting to enjoy a night out – we will create a safe and memorable evening in our Dining Room. With premium Prime steak options on our Dinner Menu as well as best-in-class seafood and innovative plant-based options, we have something to offer everyone you are dining with.

A photo of Bar Italia Winter Park restaurant

6. Bar Italia Winter Park

4.7

Exceptional(691)

Price: Expensive

• Italian • Winter Park

Booked 98 times today

Hello Winter Park - We are beyond excited to welcome you to Bar Italia! We will be open for dinner service only starting Monday, March 27th at 4:00pm. We will be brining lunch to you soon! Mangia! Fresh pasta, and homemade sauces in a stunning restaurant.

A photo of Christner's Prime Steak and Lobster restaurant

7. Christner's Prime Steak and Lobster

4.8

Exceptional(4778)

Price: Very Expensive

• Steak • Winter Park

Booked 80 times today

The Christner family invites you to join them at Orlando's favorite steakhouse. Opened in 1993, Christner's is truly a family business "we have very little turnover because our employees are part of the family"! Our customers are locals...business people... travelers...vacationers and sports stars...including many celebrities. Everyone agrees...outstanding menu...professional staff and America's Most Award Winning Steakhouse! The Christners maintain an informal flavor of warm, hands-on, personal hospitality. As Russ said, "Hey, we're just a humble little steakhouse" Enter a guest, leave a friend. Reservations for Private Rooms must be made in advance by calling the restaurant directly at 407.645.4443.Bread: Baked fresh daily and served piping hot to your table. Rip it. Break it. Just don't cut it with a knife.Beef: USDA Prime, aged corn-fed straight from the Midwest and cut to order.Lobster: Cold Water Australian

A photo of Antonio's - Maitland - Upstairs restaurant

8. Antonio's - Maitland - Upstairs

4.6

Exceptional(1805)

Price: Expensive

• Italian • Maitland

Booked 23 times today

Antonio's has built a reputation for high quality, great value and friendly service. Our menu features authentic Northern and Coastal Italian cuisine. We prepare a wide variety of original seafood, veal, steaks and pastas with the freshest ingredients, at competitive prices. To complete your experience we offer an extensive bottle wine list, a full liquor bar and warm, gracious service in a comfortable and elegant atmosphere overlooking Lake Lily.

A photo of Boca - Winter Park restaurant

9. Boca - Winter Park

4.5

Awesome(1256)

Price: Moderate

• American • Winter Park

Booked 67 times today

Boca - Winter Park is a perfect spot for a date night. With a cozy and comfortable neighborhood ambiance, it's described as a 'great date night spot' by a reviewer. The food and service are consistently rated highly, making it a great choice for a romantic evening out. The creative and well-executed menu, beautiful space, and laid-back atmosphere only add to the appeal.

A photo of The Tap Room at Dubsdread restaurant

10. The Tap Room at Dubsdread

4.8

Exceptional(3161)

Price: Expensive

• American • Downtown Orlando

Booked 82 times today

Our spectacular setting and award-winning food have made us a favorite in Central Florida. Join us for lunch, dinner or happy hour inside or out on the verandah. We proudly offer fresh fish, hand-cut prime steaks, homemade desserts and Orlando’s best burger!

‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

See what locals rave about

From verified diners like you

L
LuisVIP
Orlando / Central Florida East •10 reviews
5.0
Dined 3 days ago
The experience is always amazing! The food is outstanding every time. The service comes by every couple minutes for table bread, water, and drinks. The location and people are great, eye worthy, and outgoing. The only ouch to the night, is the Bill. My 17 yr old daughter and myself: 2 apps 3 meals (Seabass, Risotto, Filet) 1 Creme Brulee 2 wines by the glass $320.00 with 18% included. The Ouch!
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AVA MediterrAegeanPrice: Expensive• Mediterranean• Winter Park
•
4.7
C
Connie
Orlando / Central Florida East •2 reviews
5.0
Dined 4 days ago
Beautiful evening spent at Jazz Tastings. They got it all right - food, lighting, volume of live music, and most importantly, outstanding service. We will be back soon!
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Jazz TastingsPrice: Expensive• American• Maitland
•
4.8
S
Shannon
Orlando / Central Florida East •1 review
5.0
Dined 4 days ago
Bar Italia never disappoints! Our server Audrey pays close attention to detail, is very friendly and kind- and the manager Braden is always welcoming!
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Bar Italia Winter ParkPrice: Expensive• Italian• Winter Park
•
4.7
M
Mariana
San Diego •2 reviews
5.0
Dined 5 days ago
I absolutely loved Bulla Gastrobar! I would rate it a 10/10 for the ambiance, service, and food. Everything we ordered was delicious, and the overall experience was amazing. I highly recommend making a reservation, as the place gets quite busy. Definitely a must-visit!
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Bulla Gastrobar - Winter ParkPrice: Moderate• Spanish• Winter Park
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4.8
A
Amanda
Orlando / Central Florida East •1 review
5.0
Dined 7 days ago
The Pumbaa is excellent. The Christmas overlay was great—funny and festive and yummy. Our second trip and we will definitely be back.
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Permanent VacationPrice: Moderate• American• Maitland
•
4.9

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Maitland

Best Date Night Restaurants in Maitland

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52 restaurants available nearby

1. Jazz Tastings

2. AVA MediterrAegean

3. Permanent Vacation

4. AJ CHOCOLATE HOUSE

5. Fleming's Steakhouse - Winter Park

6. Bar Italia Winter Park

7. Christner's Prime Steak and Lobster

8. Antonio's - Maitland - Upstairs

9. Boca - Winter Park

10. The Tap Room at Dubsdread

See what locals rave about

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