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Old Town Key West offers charming boutique hotels and cozy bungalows with amenities like pools, spas, and beach access, all within walking distance to the vibrant Duval Street. These accommodations provide a blend of historic charm and modern comforts, perfect for couples seeking an intimate and authentic Key West experience under $500 a night.

Key West

Offering an outdoor pool, Duval Inn is located in Key West. Free WiFi access is available.

This Key West bed and breakfast includes both an indoor and outdoor seating area as well as a refrigerator. The private bathroom includes free toiletries. Beds are outfitted with linens.

Learn about the life and times of writer Ernest Hemingway at Ernest Hemingway Home and Museum (500 m) or view the sights and venues of Duval Street (100 m). Mallory Dock is located 12 minutes' walk away.

Duval Inn - Key West

Located less than 3 blocks from the beach and Duval Street, this classic-style Key West motel features Cuban tile floors and a beautiful rooftop sun deck. Free Wi-Fi is available.

The relaxing, tropically themed rooms of El Patio Motel are equipped with cable TV and a refrigerator. A telephone and air conditioning are included.

An outdoor pool and lush garden are open to all guests of El Patio. The hotel staff is also happy to help arrange activities or rent bicycles to travel around Key West.

El Patio Motel is a 7-minute walk from the Key West Butterfly and Nature Conservatory. The Key West Shipwreck Museum is less than 2 miles away.

El Patio Motel

This Key West Hilton Garden Inn from the The Keys Collection is 2 minutes' drive from the Key West International Airport and 10 minutes' drive from Duval Street. Features include a restaurant, tiki bar, and rooms with free WiFi.

Rooms are non-smoking and are furnished with a microwave, refrigerator, and cable TV as well as a coffee machine. Some rooms have a balcony and a sofa bed.

A hot tub is beside the outdoor pool. Guests can also take advance of an on-site business centre and fitness centre. An hourly shuttle is available to the Key West city centre and Old Town. Bicycles are available for a fee.

The Garden Grille restaurant is open for breakfast buffet and dinner. Tiki bar is located poolside and offers cocktails, drinks and snacks. Additionally, the concierge service can arrange Key West experiences.

The Ernest Hemingway Home 5.7 km from the property. Old Town Trolley Tours is less than 3.2 km from the Hilton Garden Inn Key West The Keys Collection. The Southernmost Point is 5 km from the property. Mallory Square is 6.4 km away. Stock Island Marina is 2.5 km from the Hilton Garden Inn.

Hilton Garden Inn Key West / The Keys Collection

This bed and breakfast welcomes guests to Old Town, Key West and boasts a free continental breakfast, 3 outdoor pools and a hot tub. The Ernest Hemingway Home and Museum is 15 minutes’ walk away.

Free WiFi access and a flat-screen cable TV are provided in each room at this Key West NYAH - Adult Exclusive bed and breakfast.

Guests can stroll through the garden or ask the tour desk for area recommendations. The 24-hour reception offers luggage storage.

The nightlife, shops, and art galleries of Duval Street are 9 minutes’ walk from the property. Key West Aquarium and Key West Cruise Port are each 1.2 km away.

Nyah - Adult Exclusive

Offering 2 outdoor pools, this Old Town Key West motel features high-speed WiFi access and a cable TV in each room. Duval Street is 2 minutes' walk away.

All rooms include a microwave, refrigerator, hair dryers, and plush eurotop mattresses. Extras include daily continental breakfast, convenient bicycle and e-scooter rentals on-site, beach access, and our Tipsy Rooster Bar and Liquor Store.

A concierge desk and luggage storage are available at Southwinds Motel. Parking is available on-site. A launderette is also at the property.

The Ernest Hemingway Home and Museum is 12 minutes' walk away. Guests at the property can rent bicycles to explore the area. Fort Zachary Taylor Historic State Park is less than 3.2 km away.

Southwinds Motel

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Hotels in Old Town Key West with pool near Duval Street under $500 (Oct 2025)

Parking

Restaurant

Pets allowed

Room service

Meeting/banquet facilities

24-hour front desk

Tennis court

Sauna

Fitness centre

Golf course (within 3 km)

Garden

Terrace

Non-smoking rooms

Airport shuttle

Fishing

Business centre

Babysitting/child services

Laundry

Dry cleaning

Continental breakfast

Facilities for disabled guests

Skiing

Barber/beauty shop

Family rooms

Games room

Casino

Breakfast in the room

Ironing service

Free parking

Internet services

Lift

Express check-in/check-out

Solarium

Safety deposit box

Valet parking

Currency exchange

Spa and wellness centre

Massage

Children's playground

Billiards

Table tennis

Karaoke

Windsurfing

Darts

Hot tub/Jacuzzi

Soundproof rooms

Canoeing

Hiking

Chapel/shrine

BBQ facilities

Packed lunches

Car hire

Cycling

Bowling

Tour desk

Hammam

Heating

Fax/photocopying

Diving

Horse riding

Squash

Snorkelling

Luggage storage

WiFi

Mini golf

Ski storage

Ski school

Allergy-free room

Indoor pool

Outdoor pool

Free WiFi

Non-smoking throughout

Air conditioning

Designated smoking area

ATM/cash machine on site

Private beach area

Restaurant (à la carte)

Restaurant (buffet)

Snack bar

Sun terrace

Outdoor pool (all year)

Outdoor pool (seasonal)

Indoor pool (all year)

Indoor pool (seasonal)

Concierge service

Entertainment staff

Nightclub/DJ

Private check-in/check-out

Shuttle service (free)

Shuttle service (additional charge)

Ski equipment hire on site

Ski pass vendor

Ski-to-door access

Special diet menus (on request)

Trouser press

Vending machine (drinks)

Vending machine (snacks)

Water sport facilities on site

Hot spring bath

General

Activities

Services

Room Amenities

Bathroom

Media & Technology

Food & Drink

Services & Extras

Outdoor & View

Internet

Kitchen

Outdoors

View

Living Area

Bedroom

Layout

Accessibility

Building characteristics

Pool and wellness

Transport

Reception services

Common areas

Entertainment and family services

Cleaning services

Business facilities

Shops

Miscellaneous

Bath/Hot spring

Hostel facilities

Safety & security

Your sustainability practices

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Hygiene

Physical distancing

Cleanliness & disinfecting

Food & drink safety

Self check-in

Exclusive services