Hotels in Key West, Florida with Pool

Key West hotels (11 - 20 of 33)  

Southernmost on the Beach

4 stars 508 South Street
Key West, FL 33040
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The brand new and renewed Southernmost on the Beach, in historic old town, stretches out on a secluded section of the island, away from the hustle of Key West activities, but close enough to the excitement when you want it. The Southernmost on the Beach hotel's private beach and pier offer front row seats to the Atlantic Ocean's spectacular sunrises and winter sunsets. All guests take pleasure in resort amenities including the junior size Olympic swimming pool - now with an oceanfront bar, Private Pier stretching over the Atlantic, the beachfront open-air Southernmost Beach Cafe and a real sand beach with chaise lounges for relaxing. Additional inclusive amenities are: parking, wireless internet, resort activities, gym, concierge services with on-site bicycle and moped rentals and a walk-everywhere location in historic old town. The new 80 guestrooms feature dark mahogany furniture, the tranquility of blue and white decor, and ocean views that suggest a private yacht. Whether you decide on a restful ocean view, an oceanfront room, each one artfully combines a tropical modern motif with a nautical feel to make you feel right at home.

Santa Maria Suites Resort

4 stars 1401 Simonton Street
Key West, FL 33040
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Experience a truly sophisticated and contemporary Key West, Florida resort when you choose The Santa Maria Suites. Barely a block from the Atlantic Ocean and Duval Street, the elegantly refined all-suites hotel is nothing short of breathtaking. The charm of Key West along with spacious suites and gracious amenities await you at our hotel in Key West, Florida. Guest suites with private balconies and terraces enclose a secret garden sanctuary. The clever attention-to-detail extends to each of our stunning two-bedroom guest suites. The kitchen amenities alone are enough to inspire your culinary flair. Dove® candies on your pillow at turndown service, Bath & Body Works® bath products and full concierge services are other elegant perks you'll remember long after you've returned home.

Alexander Palms Court

3 stars 715 South Street
Key West, FL 33040
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Tropical setting with towering palms located only 2 blocks from the Ocean and Duval Street. Enjoy our spacious rooms and suites, pillow top mattresses, rainforest showerheads and island breakfast. Relax in our pool or courtyard.If there are more then 2 people in the room, the Alexander Palms Court charges 20 USD for each additional guest. Children over 12 will be charged as an adult.

Duval House

3 stars 815 Duval Street
Key West, FL 33040
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A romantic, quiet getaway for honeymooners and couples (children under the age of 16 are discouraged) located on Duval Street. Seven Houses, most of which are century old Victorians that have been restored, center around a lush tropical garden and swimming pool. We serve a complimentary breakfast poolside every morning. All of the rooms include private bathroom, air conditioning, cable TV, color TV and are non-smoking. We offer many additional suites and unique rooms not shown on our website. Please contact Duval House for details on those specific rooms. Located in the heart of Old Town Key West.

Almond Tree Inn

3 stars 512 Truman Ave
Key West, FL 33040
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This 22 room elegant inn is a tropical oasis in the heart of old town, just one half block off Duval Street and an easy walk to restaurants, shops, and other attractions. Exquisitely appointed guest rooms are fully equipped with 27 inch color TV with movie and sports channels, radio, air conditioning / heat, refrigerators, microwave ovens, digital safes, ceiling fans, coffee makers, hair dryers, irons, robes and two-line phones with voice-mail and computer data ports. All rooms are non-smoking. The Almond Tree has all the amenities of a B and B with complimentary continental breakfast and happy hour with free beer, wine and soft drinks. Cool off in our sparkling pool or relax in our bubbly spa. Off-Street Parking: One parking space is available for each guest room at only $5.00 per day. All guests must be 25 years or older unless accompanied by a parent. Just off Duval Street

Silver Palms Inn

3 stars 830 Truman Avenue
Key West, FL 33040
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Welcomes you with island inspired charm, inviting deals, and rates to suit your budget. Whether you are indulging in a longer luxurious Holiday or a Key West weekend getaway, come experience authentic Old Town Key West at the Silver Palms Inn, your home away from home.Key West Hotel Amenities. Enjoy the Silver Palms Inn and your Key West Vacation with complimentary amenities including: Daily continental breakfast, Wi-Fi and Wired internet, Parking, Fitness Room, and much more! View the entire list of amenities.

Pearl's Key West

3 stars 525 United Street
Key West, FL 33040
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Pearl's Guesthouse offers a relaxed and welcoming atmosphere in the American Caribbean for adults over 21.

***Please note..All guests booking during Spring Break must be 25yrs old to checkin with a valid drivers license.***

The award winning property features historic buildings (including a renovated cigar factory), lush landscaping, two heated pools, two hot tubs and Pearl's Patio bar and grill. We combine guesthouse ambience with resort amenities that include concierge service, free Wi-Fi, on-site massage and the Strand restaurant, which serves cooked to order breakfast daily. Our 38 rooms and suites range from the simple to the deluxe to satisfy a variety of budgets. All rooms are Non-Smoking. Pearl's, as an all-welcoming, mostly adult, gay-friendly, straight-friendly resort,embodies the true One Human Family spirit that makes Key West Key West.Pearl's Guesthouse is ideally located in America's southernmost city, just a half block from Duval Street and two blocks from the Atlantic Ocean. All the major attractions of Key West are within walking or biking distance and biking is a great way to get around on our small island. Friendly staff can arrange for all kinds of excursions: fishing, snorkeling, kayaking, even sky-diving and more to complete your Keys experience. Behind the gates of Pearl's is the place to catch the spirit of Key West - Pearl's Patio, Key West's Cozy Tropical Bar. Open daily starting at noon, the bar offers happy hour on weekdays, daily activities and frequent special events.

Courtyard by Marriott Key West Waterfront

3 stars 3031-41 North Roosevelt Boulevard
Key West, FL 33040
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Get FREE high-speed Internet access at the Courtyard Key West Waterfront. This Key West hotel is located on the Gulf of Mexico in the "New Town" section of Key West. The Courtyard Key West is located within a 10 minute drive of any attraction on the island and features spacious guest rooms and suites. It features a large outdoor junior olympic size heated swimming pool and nearby hot tub, a Tiki Bar located adjacent to the pool, a private sunbathing beach, a 300 foot observation boardwalk, a free computer workstation in the lobby, complimentary in-room refrigerators and laptop size safes, and a concierge agent to help you plan your Key West vacation. Look for our Advance Purchase packages for our "Suite" deals including breakfast!Complimentary shuttle service is available to and from the downtown Key West area from 8am to 11pm.

Doubletree' Grand Key Resort

3 stars 3990 S. Roosevelt Blvd
Key West, FL 33040
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Welcome to DoubleTree by Hilton Hotel Grand Key Resort – Key West, where a friendly staff member is waiting to welcome you with a freshly baked chocolate chip cookie. Everything you need is available in the hotel, from a 24-hour business center to three meals a day served in the full-service Palm Haven Restaurant.Relax in luxury at our first-class Key West, Florida resort. The DoubleTree by Hilton Hotel Grand Key Resort - Key West is perfect for your next tropical getaway to the Florida Keys.Start your day with a delicious Wake Up DoubleTree Breakfast and enjoy complimentary high-speed internet access in your guest room. Upgrade to a superior room and enjoy a superb balcony view that overlooks lush tropical landscaping. The pool features a waterfall, whirlpool, and large sunbathing decks ideal for lounging while sipping a refreshing cocktail from the Tiki Bar. Hold your business meeting or social event for up to 300 guests in one of our seven venues.Stay at our Key West, Florida resort, just 1 mile from Key West International Airport, and take advantage of the complimentary hotel shuttle service to the beaches, the marinas, and downtown Key Wes

Sunrise Suites Resort

3 stars 3685 Seaside Drive
Key West, FL 33040
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Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom, 2 bath condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse Museum, Discovery Undersea Tours (glass-bottom boat), Dry Tortugas National Park Ferry, Wrecker's Museum (oldest residence), Old Town, Mallory Square, Audubon House and Tropical Gardens, and Truman's Little White House. Many species of birds inhabit the salt ponds preserve that borders this property.
These suites are considered vacation rentals and offer 2 bedroom 2 bathroom condos for the price of a hotel. All suites include 900 square feet of comfortable space and private balcony fully equipped kitchens, spacious living rooms, wireless internet and hair dryers. Each suite is individually owned and decorated to the owners taste.
Guests enjoy hotel amenities include the lagoon-shaped heated swimming pool, jacuzzi, tennis court, gym facilities, laundry facilities, concierge service, internet, fax and copy service, and bike rentals.
Maid service is optional and available on a daily basis for $10 per day. Guests interested in this service can inquire at time of check-in. Free towel exchange is available upon request.
Well trained pets under 20 pounds are welcome at the hotel with a $35 fee plus tax charged for each night they stay. Please note the resort must be given prior notification to qualify pet for your stay and no more than one pet is allowed in a suite. Only certain units allow pets.
Please note the hours of the front desk: 9am - 8pm M-F
All fees subject to change without notice. Minimum check-in age is 25. All guests must be at least 25 years of age except children accompanied by a legal guardian.