The Best Hotels in Uptown - Upper Duval, Key West - 2026 Updated Prices

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Compare popular hotels in Uptown - Upper Duval

Property	Property class	Guest rating
Orchid Key Inn - Adults Only	3.5 star property	9.8 Exceptional 1,006 reviews	View
Douglas House - Adults Only	3.0 star property	9.6 Exceptional 512 reviews	View
H2O Suites - Adults Only	3.5 star property	9.8 Exceptional 650 reviews	View
Southernmost House - Adult Exclusive	4.0 star property	9.4 Exceptional 1,001 reviews	View
Santa Maria Suites	4.0 star property	9.6 Exceptional 1,001 reviews	View

Where to stay in Uptown - Upper Duval

Find the best Uptown - Upper Duval areas for the activities you enjoy most.

A white lighthouse with a small adjacent building, surrounded by lush green trees and a clear blue sky.

Old Town Key West

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

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A sunset over a coastal landscape with a small island surrounded by water.

Stock Island

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A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

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A two-story house with green shutters and a wooden balcony.

Key West Historic District

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.

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A row of pastel-colored houses with white railings and a clear blue sky.

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Key West Tropical Forest and Botanical Garden.

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Top Uptown - Upper Duval Hotel Reviews

Southwinds Motel

10/10 Excellent

"Southwinds Motel has to be the absolute best spot I’ve stayed at when it comes to conveniences on site along with an awesome location and proximity to sites and activities. Perfectly located around the Southernmost part of Key West, Southwinds gives you fully stocked bar WITH a built-in liquor store. Super convenient off rip. Bar has live music in the afternoon and evening, a pretty nice pool and deck area and, what I really found most convenient, access to rentals for any means of transportation you need for Key West from bicycles to scooters to full sized golf carts. Rentals are provided by Bone Island rentals who also deliver your mode of moving around to the property and picks it up from the property. A totally ‘Key West’ luxury in my mind. So you’re not staying in the fanciest of shindigs, but you rented a motel because you probably plan to be out and about in beautiful Key West and not cooped up, so you most definitely shouldn’t have grand expectations, but you definitely won’t be disappointed with the digs either. Another thing I really appreciated was after check-in, we were also gifted 2 vouchers for free specialty cocktails from their bar. It was small drinks and only their specialty drinks but still complimentary, so we say thank you and enjoy. They let us combine both tickets for one full sized rum runner my wife enjoyed. Overall 10/10 for comfort, convenience, location and it’s vibe. Will absolutely be going back and 100 percent recommend to all staying in KW"

Douglas House - Adults Only

10/10 Excellent

"Loved this property. Have been coming to KW for last 40+ years and never stayed here? Great location. Our room was more like and apartment. We were down from Miami for rum festival and were close to all of the different events at Douglas. The property was meticulously kept. The staff was helpful. Plenty of parking on street and close to the moondog cafe and so many other places to eat and drink. Highly recommend this property. Will be back."

Beachside Resort & Residences

8/10 Good

"Hot tub wasn’t working. It was just warm water. Gym was very hot. Beach wasn’t great. Elevator in my building wasn’t working g but you can use the one from the building next to it and walk over. So not that bad. Pool was great. Never crowded. Room was excellent. We had a suite with pool access. There was plenty of parking at the hotel and no charge to park We would still go back again."

Frequently asked questions

What is Uptown - Upper Duval like?

Travellers will be sure to find plenty to entertain them in Key West's Uptown - Upper Duval neighbourhood. Experience the best of Uptown - Upper Duval with a visit to Duval Street and Florida Keys Beaches during your trip.

Where is the best place to stay in Uptown - Upper Duval?

Based on our traveller data, Southernmost Beach Resort and Guesthouses is one of the top choices for your stay in Uptown - Upper Duval. This hotel is steps from South Beach, and offers 3 outdoor pools and a full-service spa. Other good choices for your stay in the neighbourhood include The Reach Key West, Curio Collection by Hilton and Southwinds Motel.

How many hotels will I find in the Uptown - Upper Duval area?

If you're searching for places to stay in Key West, Expedia has something to meet your needs with 242 Uptown - Upper Duval hotels and other accommodation options to choose from.

If I need to cancel my hotel reservation in Uptown - Upper Duval, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable provided that you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of your booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to view the top deals on offer in Uptown - Upper Duval.

What are the top things to see and do in Uptown - Upper Duval?

Florida Keys Beaches, South Beach and Simonton Beach are great spots if you want to spend some time by the water during your stay in Uptown - Upper Duval. You could also plan a visit to Duval Street or Key West Butterfly and Nature Conservatory while you're in the neighbourhood. A few places to visit in the area around Uptown - Upper Duval include City Zoo Gallery, Southernmost Point and Tennessee Williams Key West Exhibit. While you're out sightseeing in Key West, make sure that you visit other sights such as Key West Lighthouse and Keeper's Quarters Museum or Ernest Hemingway Home and Museum.

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Our top choices for Uptown - Upper Duval hotels

1. Santa Maria Suites

2. The Southernmost Inn - Adults Only

3. Southernmost Beach Resort and Guesthouses

4. H2O Suites - Adults Only

5. Southwinds Motel

6. Orchid Key Inn - Adults Only

7. Douglas House - Adults Only

8. Southernmost House - Adult Exclusive

9. The Reach Key West, Curio Collection by Hilton

10. Kona Kai Oasis

11. Sea Breeze by Brightwild Off-street Parking

12. Keys Please by Brightwild Pool Steps to Duval

13. Almond Tree Inn Hotel - Adults Only

14. Lighthouse Hotel - Key West Historic Inns

15. Paradise Inn Key West - Adults Only

16. Winslow's Bungalows - Key West Historic Inns

17. Silver Palms Inn & Historic Homes

18. Island City House Hotel

19. Duval House

20. The Marquesa Hotel

Compare popular hotels in Uptown - Upper Duval

Where to stay in Uptown - Upper Duval

Old Town Key West

Stock Island

Downtown Key West

Key West Historic District

New Town

Top Uptown - Upper Duval Hotel Reviews

Southwinds Motel

Frequently asked questions

Explore a world of travel with Expedia