Top-Rated Key West Hotels with Pool

We checked thousands of reviews on and to find the best hotels for your stay
Go to Hotel List View map

Alardo Riojas

Updated: 10 January 2024 · 6 min

Key West, the southernmost point of the United States, beckons travelers with its warm, inviting climate, vibrant history, and picturesque beaches. For many, the idea of the perfect Key West experience is incomplete without a place to stay that complements the island's laid-back atmosphere and natural beauty. Hotels with pools provide an oasis of relaxation and leisure, offering a serene escape from the bustling streets and a refreshing break under the Florida sun.

Choosing the right hotel with a pool in Key West can significantly enhance your vacation experience. Imagine starting your day with a tranquil swim in a beautifully designed pool, surrounded by lush tropical gardens, or perhaps ending an afternoon of exploration by lounging poolside as the sun sets. These hotels offer more than just a place to stay; they provide a sanctuary where guests can unwind, refresh, and create lasting memories amidst the island's enchanting environment.

Our article aims to guide you through the top rated Key West hotels with pool amenities, ensuring that you find the perfect match for your stay. We've curated a list that includes a variety of options, from luxurious resorts with expansive pool complexes to quaint, boutique hotels with intimate pool settings. Whether you're planning a romantic getaway, a family vacation, or a solo retreat, discover how these Key West accommodations can add a splash of delight to your trip.
Show more + Show less -

Our Top 10

(Sorted by rating & number of reviews)

1. Casa Marina Key West, Curio Collection By Hilton Hotel
2. Pier House Resort & Spa
3. Ocean Key Resort & Spa, A Noble House Resort
4. Chelsea House Hotel - Key West
5. Orchid Key Inn - Adults Only
6. Opal Key Resort & Marina
7. Simonton Court Historic Inn & Cottages
8. The Gardens Hotel
9. Hyatt Centric Key West Resort & Spa
10. Sunset Key Cottages

Luxury Key West Hotels with Pool

Check Availability

Key West
Dec 13, 2025 - Dec 14, 2025

Casa Marina Key West, Curio Collection By Hilton Hotel

5.6

Good

(332 Reviews)

+ 140 photos
Nestled on the edge of the island, Casa Marina Key West stands as a beacon of luxury. This historic hotel combines the elegance of the early 20th century with modern sophistication, and its sprawling pools are a testament to its commitment to luxury. Guests can choose between two oceanfront pools, each offering a distinct atmosphere – one for lively family fun and the other for tranquil adult relaxation. Surrounded by private cabanas and with direct access to a private beach, the pools serve as the heart of the resort. The hotel’s emphasis on providing a serene pool experience is matched by its luxurious accommodations and exceptional service, making it a premier choice for discerning travelers seeking a top-tier Key West hotel with a pool.
Address: 1500 Reynolds Street
Rating: Good 5.6 (332 Reviews)
Rooms: 311
Price: From 440$

Pier House Resort & Spa

8.1

Good

(627 Reviews)

+ 180 photos
Pier House Resort & Spa is located at the edge of Key West Harbor, offering its guests a front-row seat to stunning sunsets and crystal-clear waters. The beachfront pool and spa provide a luxurious setting to unwind, accompanied by the sound of the waves. The resort’s unique location also allows for easy access to Key West’s vibrant nightlife and historic landmarks. With fine dining options and a private white sand beach, Pier House Resort is the quintessential destination for those desiring a Key West hotel with a pool and captivating ocean views.
Address: One Duval Street
Rating: Good 8.1 (627 Reviews)
Rooms: 142
Price: From 471$

Family-Friendly Key West Hotels with Pool

Family vacations in Key West are made unforgettable with stays at hotels that cater to the needs and entertainment of all ages. In this section, we dive into hotels that not only feature magnificent pools but also ensure a family-friendly environment. These hotels offer pools with varying depths, lifeguard services, and engaging activities, making them ideal for children and adults alike. Additionally, with amenities like kid's clubs, adjacent water parks, or poolside snack bars, they promise a hassle-free and enjoyable stay for the whole family. Embrace the warmth of Key West and the joy of family time with these select hotels that serve as a perfect base for a memorable vacation.

Ocean Key Resort & Spa, A Noble House Resort

8.4

Good

(143 Reviews)

+ 327 photos
Ocean Key Resort & Spa stands as a beacon of romance on the edge of Key West, where the Gulf of Mexico meets the Atlantic Ocean. The hotel’s waterfront pool offers an idyllic setting for couples to reconnect, featuring magnificent views, private cabanas, and a lively yet intimate atmosphere. Ocean Key’s emphasis on providing a romantic escape is evident in its luxuriously appointed suites, spa services designed for two, and dining experiences that cater to lovebirds. The pool area, with its breathtaking sunset views, becomes a nightly spectacle, creating unforgettable moments under the sky’s changing hues. For couples seeking both adventure and relaxation, Ocean Key Resort & Spa offers a romantic Key West hotel with a pool that truly captures the essence of a lovers' paradise.
Address: Zero Duval Street
Rating: Good 8.4 (143 Reviews)
Rooms: 100
Price: From 904$

Chelsea House Hotel - Key West

8.5

Good

(1453 Reviews)

+ 51 photos
Chelsea House Hotel offers a quaint, charming setting perfect for families wanting a quieter stay without sacrificing the joys of a great pool. This historic boutique hotel features a large, heated outdoor pool nestled within its beautifully landscaped gardens, providing a tranquil retreat for families. The pool area, with its ample lounging opportunities and gentle waters, becomes a gathering spot where memories are made. Chelsea House also prides itself on providing family-friendly accommodations within easy reach of Key West’s most beloved child-friendly attractions. With its combination of historic charm, modern comfort, and a commitment to ensuring guests of all ages have a splendid time, Chelsea House is a delightful choice for families exploring Key West hotels with pools.
Address: 709 Truman Ave
Rating: Good 8.5 (1453 Reviews)
Rooms: 37
Price: From 168$

Romantic Key West Hotels with Pool

For couples seeking a romantic getaway in Key West, hotels with intimate pools create the perfect backdrop for love and connection. In this section, we highlight hotels known for their serene pool areas, breathtaking views, and attention to detail, all of which contribute to an unforgettable romantic escape. These accommodations offer secluded poolside spots, luxurious amenities, and settings that inspire romance under the Florida sun. From private cabanas to evening poolside cocktails, every element is designed to enhance the couple’s experience. Dive into the romance of Key West with these selected hotels, where poolside moments are just the beginning of the magic.

Orchid Key Inn - Adults Only

9.4

Good

(260 Reviews)

+ 102 photos
Orchid Key Inn presents an exquisite boutique hotel experience where luxury meets the laid-back Key West lifestyle. Located on Duval Street, this hotel offers an escape within the heart of the city. The pool area, a tranquil oasis, is surrounded by lush tropical landscaping, offering a peaceful retreat. The Orchid Bar, adjacent to the pool, serves up signature cocktails in this serene setting. Guests can immerse themselves in the quiet sophistication of their rooms after a refreshing swim. Orchid Key Inn is the perfect blend of modern amenities and classic charm, making it an ideal choice for travelers seeking a boutique hotel in Key West with a pool.
Address: 1004 Duval Street
Rating: Good 9.4 (260 Reviews)
Rooms: 24
Price: From 156$

Opal Key Resort & Marina

8.6

Good

(1440 Reviews)

+ 60 photos
Margaritaville Key West Resort & Marina captures the essence of a laid-back family vacation with its delightful pool area that invites guests of all ages to soak up the sun. The pool, with its shallow areas for kids and comfortable seating for adults, is the perfect place to unwind after a day of Key West adventures. Themed daily activities keep the young ones entertained, while the poolside bar serves up refreshing concoctions that can be enjoyed by the whole family. The resort’s airy rooms, some of which offer stunning views of the Gulf of Mexico, combine comfort with the island's tropical flair. With its prime location and family-oriented amenities, Margaritaville stands out as a captivating Key West hotel with a pool for families seeking both relaxation and adventure.
Address: 245 Front Street
Rating: Good 8.6 (1440 Reviews)
Rooms: 194
Price: From 505$

Budget-Friendly Key West Hotels with Pool

Discover the charm of Key West without breaking the bank at these budget-friendly hotels, where great value meets tropical relaxation. This section showcases accommodations that provide affordable options without compromising on the pool experience. Guests can enjoy well-maintained pools, comfortable rooms, and convenient locations close to Key West's attractions. These hotels prove that you don’t have to spend a fortune to enjoy the beautiful pools and sunny climate of Key West. Whether you're a solo traveler, a couple, or a family, these selections offer a welcoming base for exploring the island's delights while staying within budget.

Simonton Court Historic Inn & Cottages

9.2

Good

(1090 Reviews)

+ 248 photos
Simonton Court Historic Inn & Cottages is a quaint hideaway set in the heart of Old Town Key West. This adults-only hotel is comprised of restored conch houses and cottages, offering a unique historical ambiance. The property features four pools, each tucked away in different sections of the lushly landscaped grounds, providing plenty of private alcoves for guests. The inn’s commitment to preserving the charm of Key West while offering modern luxuries makes it a standout. Simonton Court is an inviting option for travelers seeking a historic, boutique hotel with pool facilities that promise a peaceful retreat.
Address: 320 Simonton St
Rating: Good 9.2 (1090 Reviews)
Rooms: 30
Price: From 434$

The Gardens Hotel

9.6

Good

(142 Reviews)

+ 158 photos
Nestled in the center of Key West is often described as a romantic paradise, perfect for couples seeking a serene and intimate experience. The hotel’s lavish pool area feels like a secluded sanctuary, with lush tropical gardens enveloping the pool and creating an atmosphere of privacy and exclusivity. Couples can unwind in the serenity of the garden pool, savoring the peace and quiet or enjoying a romantic poolside drink. The attention to detail extends to every corner of The Gardens Hotel, from the elegantly appointed rooms to the personalized service, ensuring a romantic getaway that is both luxurious and heartfelt. With its enchanting setting and dedication to creating memorable experiences, The Gardens Hotel stands out as a premier Key West hotel with a pool for couples.
Address: 526 Angela Street
Rating: Good 9.6 (142 Reviews)
Rooms: 22
Price: From 539$

Boutique Key West Hotels with Pool

Discover the charm and personalized service of boutique hotels in Key West, where smaller scale does not mean compromising on quality or comfort. These hotels offer unique, sophisticated settings with pools that provide an intimate ambiance away from the crowd. Enjoy the blend of personalized attention, distinctive design, and tranquil poolside relaxation that these boutique accommodations have to offer.

Hyatt Centric Key West Resort & Spa

8.2

Good

(619 Reviews)

+ 196 photos
Hyatt Centric Key West Resort and Spa presents a family-friendly sanctuary where every member can find their slice of paradise. The hotel’s pool is a gem, featuring a shallow entry point suitable for younger swimmers and ample lounging space for parents to relax while keeping an eye out. Poolside activities designed for families ensure that the fun extends beyond swimming, making every day a new adventure. Beyond the pool, the resort offers spacious family rooms, direct beach access, and a range of water sports that cater to all ages. Its central location also means that Key West’s top attractions are just a short stroll away, providing ease and convenience for family explorations.
Address: 601 Front Street
Rating: Good 8.2 (619 Reviews)
Rooms: 118
Price: From 608$

Sunset Key Cottages

9.2

Good

(108 Reviews)

+ 186 photos
Isolated on its own 27-acre island, Sunset Key Cottages offers an exclusive escape with a pool experience that is both intimate and unparalleled. The centerpiece is a stunning, zero-entry pool that seems to merge into the surrounding ocean, offering panoramic views of the Gulf of Mexico. Accompanied by a whirlpool spa and flanked by elegant cottages, the pool area provides a secluded haven for guests. Each cottage at Sunset Key is designed to provide a serene, luxurious stay, complete with gourmet kitchens, private porches, and unmatched privacy. This resort epitomizes the blend of luxury and relaxation, making it a quintessential choice for those seeking a Key West hotel with a pool that offers both privacy and prestige.
Address: 245 Front St
Rating: Good 9.2 (108 Reviews)
Rooms: 40
Price: From 760$

Key West Hotels with Pool and Ocean Views

Maximize your Key West experience with hotels that offer breathtaking ocean views alongside inviting pool facilities. There’s nothing quite like enjoying a refreshing swim with the backdrop of the Atlantic Ocean or the Gulf of Mexico. These hotels provide the ultimate in scenic relaxation, combining the best of water-based leisure with stunning vistas.

The Mermaid & The Alligator

9.3

Good

(178 Reviews)

+ 71 photos
The Mermaid & The Alligator offers a home away from home in a historic 1904 Victorian mansion. This bed and breakfast provides an intimate setting with beautiful gardens and a heated plunge pool that is perfect for a relaxing soak after a day of exploring Key West. Each room is uniquely decorated, reflecting the island’s eclectic charm. The personalized service and attention to detail ensure a special stay. This property exemplifies the essence of a secluded, boutique experience in a Key West hotel with a pool, ideal for those seeking tranquility and personalized hospitality.
Address: 729 Truman Avenue
Rating: Good 9.3 (178 Reviews)
Rooms: 9
Price: From 719$

Nestled among the lively streets and serene beaches of Key West, the allure of luxury hotels Key West offers an unparalleled experience for those seeking indulgence and relaxation. These prestigious accommodations are not just about opulent rooms and exceptional service; their pool amenities stand out as a haven of tranquility. Imagine diving into the crystalline waters of an infinity pool, with the backdrop of a golden sunset painting the sky, or enjoying a leisurely swim in a pool surrounded by the lush flora that typifies Key West's tropical landscape. These luxury hotels have mastered the art of creating a serene environment where every moment is a retreat, promising a stay that's as refreshing as it is memorable.

For travelers eager to immerse themselves in the vibrant pulse of Key West while enjoying the comfort of nearby, high-quality accommodations, the best hotels in Key West near Duval Street offer an ideal solution. Duval Street is the heart of Key West’s entertainment district, brimming with lively bars, quaint shops, and historic sites. Having a hotel with a pool near this area means you can explore the bustling streets and then retreat to your peaceful oasis, taking a rejuvenating dip in a pool that provides a cool respite from the Florida heat. These hotels perfectly blend convenience with luxury, allowing guests to effortlessly transition from adventure to relaxation, ensuring a vacation experience that is both dynamic and restful.