Best Key West Hotels with a Pool
Key West sits at the end of the Overseas Highway, and most of its hotels with a pool are small inns set among the wooden houses of Old Town rather than large resorts. That shapes what you get: a garden pool a few steps from your room, often with a hot tub and breakfast served nearby, within walking distance of Duval Street and the Ernest Hemingway Home and Museum. The bigger pool decks sit further out, at The Capitana Key West with its private beach area or at Coconut Mallory Resort and Marina, which has two pools. This list covers both styles, with heated pools for winter trips and adults-only inns for a quieter swim.
Key West is the last island on the Overseas Highway, closer to Havana than to Miami. Its Old Town is a grid of wooden houses, guesthouses and gardens, where Duval Street concentrates bars and restaurants and Mallory Square draws a crowd for the sunset each evening. The Ernest Hemingway Home and Museum, the Southernmost Point marker and the Historic Seaport are all within walking or cycling distance of one another.
Where to stay
Garden pools, heated pools and resort decks
A pool matters more in Key West than a first look at the map suggests. The island's beaches are small and the water off them is shallow, so many visitors end the afternoon in their hotel pool instead. In the Old Town inns, the pool is also where breakfast or the evening drinks happen, which means choosing a hotel here is largely choosing a pool atmosphere: lively on Duval Street, calm in an adults-only garden, or roomy at a waterfront resort.
In Old Town, the pool is usually the centre of a historic inn rather than one feature among many in a large hotel. Simonton Court Historic Inn & Cottages is the standout here: an adults-only property with four outdoor pools spread through its gardens, rated 9.1 from nearly a thousand reviews. Winslow's Bungalows has three pools and accepts pets, a short walk from Duval Street. The Gardens Hotel, also adults-only, has two outdoor pools and hosts live jazz in its gardens on Sunday evenings. If you want more than one place to swim without leaving the old town grid, these three are where I would start looking.
Winter in Key West is mild, but a cold front can make an unheated pool feel brisk on some evenings between December and February. Several hotels on this list heat theirs. Orchid Key Inn on Duval Street pairs a heated pool with a hot tub and an on-site bar, and holds a 9.4 rating as an adults-only inn. Ella's Cottages serves its continental breakfast beside a heated pool, and The Palms Hotel adds a picnic area with barbecue facilities and accepts pets. Lighthouse Hotel, opposite the Ernest Hemingway Home and Museum, has a heated pool with a poolside bar. For a winter trip, I would filter on this first.
If you prefer a larger pool deck and space to spread out, look beyond the inns of the old town. The Capitana Key West is beachfront, with a private beach area, a year-round outdoor pool and a hot tub, and with close to 3,000 reviews it is the most reviewed property on this page. Courtyard by Marriott Key West Waterfront sits on the Gulf of Mexico with a heated pool and a hot tub. Hampton Inn Key West FL has a heated pool with ocean views, a poolside restaurant and a shuttle to Key West Airport. Coconut Mallory Resort and Marina offers two pools and apartments with full kitchens.
Adults-only inns make up a large share of this list, and they change the feel of a pool more than any amenity does. Almond Tree Inn, rated 9.4, includes breakfast and a complimentary happy hour around its pool and hot tub. Paradise Inn surrounds its pool, which has a fountain, with brick paths and a lotus pond, and hosts a wine and cheese hour. Eden House is not adults-only but is a non-smoking Art Deco hotel, family-owned since 1975, with a pool, hot tub and sundeck in tropical gardens. For families, the family rooms at The Capitana or the apartments at Hyatt Vacation Club at Windward Pointe are a better fit.
A traveler's perspectiveMy recommendation depends on how you plan to spend the day. If you will explore Old Town on foot, from Mallory Square at sunset to the Southernmost Point, I would choose an inn inside that grid: Simonton Court for its four pools, or Orchid Key Inn for a heated pool on Duval Street itself. If the pool is the main event of your trip, The Capitana Key West or Coconut Mallory Resort and Marina give you more room. Bicycles are the easiest way around the island, and several of these hotels rent them.
Almond Tree Inn - Adults Only
Key West
298 reviews
Historic adults-only inn with a pool, hot tub, and daily breakfast
Check availabilityWhy guests love itThis is an adults-only inn, so I would not recommend it for a family trip with children, and I say so plainly. For couples and friends it makes sense: guests rate it 9.4 across 298 reviews, and it is a short walk from the Ernest Hemingway House and Museum. The outdoor pool, hot tub and sun deck are on site, a continental breakfast is included, and a happy hour offers free drinks.
Orchid Key Inn - Adults Only
Key West
285 reviews
Historic adults-only inn with a heated pool and a lively bar on Duval Street
Check availabilityWhy guests love itOrchid Key Inn is adults only, so I would not suggest it for a stay with children, whatever its labels say. For couples or friends traveling without kids, it is a strong choice on historic Duval Street: a heated pool with a hot tub, an on-site bar and a continental breakfast every morning. Rooms have a flat-screen TV and a Keurig coffee machine, and some suites add a spa bath. Guests rate it 9.4 out of 10 over 285 reviews.
The Mermaid & The Alligator
Key West
166 reviews
Garden oasis with a pool, hot tub, and sun terrace in Key West
Check availabilityWhy guests love itThe Mermaid & the Alligator is listed as adults-only, so families with children should look elsewhere in Key West. For couples, it scores 9.3 out of 10 across 166 reviews. The year-round outdoor pool, the hot tub, the sun terrace and the garden make a calm base, and rooms are air-conditioned with garden views. South Beach, the Ernest Hemingway Home and Museum and Duval Street are close by. I recommend it to adults who want a garden-focused stay near Old Town.
The Gardens Hotel
Key West
98 reviews
Adults-only oasis with two pools and live jazz in the gardens
Check availabilityWhy guests love itThe Gardens Hotel is adults-only, so families traveling with children will need another base in Key West. For adults, it offers two outdoor pools and rooms with private balconies or patios, plus free Wi-Fi, bicycle hire and massage services. Live jazz plays in the gardens every Sunday evening, and Duval Street is about a minute's walk away, so the town is right there without the noise coming in. The 9.1 score across 98 reviews is strong.
Simonton Court Historic Inn & Cottages
Key West
993 reviews
Historic adult-only inn with four pools and charming cottages
Check availabilityWhy guests love itSimonton Court is an adults-only inn, so I would not suggest it to families with children; it suits couples and friends looking for calm in Key West. Four outdoor pools spread through the property and its garden, a light continental breakfast is included, and bicycles can be hired for exploring the island. Rooms have a refrigerator and a balcony or patio, and WiFi is free. Duval Street and the Ernest Hemingway Home and Museum are close by. A 9.1 from 993 reviews is an outstanding score.
La Te Da - Adult Only, 21 or older
Key West
179 reviews
Adults-only hotel on Duval Street with a pool and entertainment
Check availabilityWhy guests love itLa Te Da is an adults-only hotel for guests aged 21 or older, on Duval Street in Key West, so it is not a choice for a family with children. A restaurant, a bar and an outdoor swimming pool are on site, with evening entertainment and a concierge service. Rooms have a flat-screen TV, free toiletries and a hairdryer. Guests rate it 9.1 from 179 reviews.
Island City House
Key West
778 reviews
Historic Key West hotel with outdoor pool and Victorian-inspired rooms
Check availabilityWhy guests love itI would choose Island City House for a Key West stay that wants Victorian character with a kitchen. Rooms are Victorian-inspired with hardwood floors, a seating area and a kitchen, and guests rate the hotel 9.0 across 778 reviews, a score I trust. An outdoor pool, a garden and free WiFi are on site, and the Key West seaport is a short walk away.
The Capitana Key West
Key West
2,942 reviews
Beachfront property with a pool, hot tub, and family-friendly amenities
Check availabilityWhy guests love itThe Capitana Key West sits on the beach with a private beach area, so families can spend the morning on the sand without leaving the property. The year-round outdoor pool is there for the afternoon, and family rooms and kitchenettes are available for those who need more space or want to prepare simple meals. Rooms have air-conditioning and balconies with sea views, and the restaurant, bar and coffee shop cover every meal.
Hyatt Vacation Club at Windward Pointe
Key West
925 reviews
Apartments with kitchens, balconies, and a year-round pool in Key West
Check availabilityWhy guests love itApartments with full kitchens, separate living rooms and private balconies make Windward Pointe an easy Key West base for families: children can nap while parents sit outside. The outdoor pool is open year-round, there is a hot tub, and the barbecue area makes a relaxed dinner simple. Bicycle hire is available on site, and fishing, scuba diving and parasailing are close by for older kids. A 9.0 score is excellent.
Douglas House Adult Only
Key West
2,291 reviews
Adults-only inn with a pool, tropical garden, and historic charm
Check availabilityWhy guests love itDouglas House accepts adults only, so I would not send families with children here; it suits couples or friends looking for a quiet base in Key West. The shared outdoor pool sits in a tropical garden, and rooms have a microwave, a refrigerator and coffee-making facilities for simple breakfasts. The Ernest Hemingway Home and Museum and the Southernmost Point are a short walk away, and pets are accepted. A score of 9 from 2,291 reviews is excellent.
Truman Hotel
Key West
3,466 reviews
Boutique hotel with an outdoor pool and modern rooms, some with patios
Check availabilityWhy guests love itTruman Hotel is a boutique hotel close to South Beach and Duval Street in Key West, so families can walk to the water and the main street. The outdoor pool and sun deck with poolside seating make an easy afternoon break from the Florida sun. Rooms have wood floors and private patios, some with a refrigerator, and a continental breakfast is served daily. WiFi is free. Guests rate it 8.9 from 3,466 reviews.
Paradise Inn - Adult Exclusive
Key West
768 reviews
Adults-only inn with a pool, hot tub, and complimentary wine and cheese hour
Check availabilityWhy guests love itParadise Inn is adults-only, so I would not suggest it to families travelling with children: they cannot stay here. It does suit parents on a trip without the kids, or adult children travelling with older parents. The landscaped grounds with brick paths and a lotus pond feel calm, the outdoor pool has a fountain and there is a hot tub. The free continental breakfast and the wine and cheese hour add to that. An 8.8 score from 768 reviews is very good.
Silver Palms Inn & Historic Homes
Key West
3,354 reviews
Historic Key West inn with an outdoor pool and private balconies
Check availabilityWhy guests love itSilver Palms Inn & Historic Homes sits in historic Key West, a short walk from the Ernest Hemingway Museum, so families can explore Old Town on foot. The outdoor pool is a cool break between outings, and every room has a private balcony, a microwave and a refrigerator, practical for snacks and simple meals. A complimentary continental breakfast is served, and covered parking spares families the search for a space.
Eden House
Key West
595 reviews
Art Deco charm with a pool and hot tub in Old Town Key West
Check availabilityWhy guests love itEden House is an Art Deco hotel in Old Town Key West, family-owned since 1975, and I find its calm, non-smoking setting suits families who want a quieter base. The pool, hot tub and sundeck sit among tropical gardens, a pleasant spot for children between outings. Duval Street is within walking distance, and bicycle rentals make it easy to explore the island together. An 8.8 score from 595 reviews is very good for an independent hotel.
Ella's Cottages - Key West Historic Inns
Key West
238 reviews
Historic boutique inn with a heated pool and tropical garden in Old Town
Check availabilityWhy guests love itElla's Cottages is a boutique historic inn in Old Town Key West, and its tropical garden and heated outdoor pool give it a quiet center after a day on foot. Rooms and suites have hardwood floors, a flat-screen cable TV and a mini-fridge, WiFi is free and a continental breakfast is served by the pool. Pets are welcome and the property has spa and wellness facilities. Guests rate it 8.6 from 238 reviews.
Ridley House - Key West Historic Inns
Key West
248 reviews
Historic boutique hotel with a pool, close to Duval Street
Check availabilityWhy guests love itWalking distance to Duval Street, museums and water sports is what I would highlight for families at Ridley House, part of Key West Historic Inns. The outdoor pool gives children a break between outings, a continental breakfast is served every morning, and pets are welcome. Rooms are air-conditioned with free WiFi. As a small historic boutique inn, it feels more intimate than a large resort, so it suits calm families best. Guests rate it 8.6 out of 10 over 248 reviews.
The Palms Hotel
Key West
2,386 reviews
Historic Key West hotel with a heated pool and pet-friendly amenities
Check availabilityWhy guests love itThe heated pool and the daily continental breakfast are why I would put The Palms Hotel on a family list for Key West. Some rooms add a kitchenette and a seating area, which helps with younger children, and there is a picnic area with barbecue facilities for an easy dinner outdoors. Bicycles can be rented on site, a good way to explore the island together, and pets are welcome. WiFi is free. An 8.5 from 2,386 reviews is a very good score.
Creme Brulee Suite
Key West
27 reviews
Pet-friendly inn with a pool and private entrances in downtown Key West
Check availabilityWhy guests love itI would pick Creme Brulee Suite for a family that wants a small inn in central Key West. Guests rate it 8.5 across 27 reviews. Rooms have private entrances, city views, a refrigerator, a microwave and a tea and coffee maker, and there is an outdoor pool, a garden and a patio with a barbecue. Simonton Street Beach and Mallory Square are close by, and pets are welcome.
Coconut Mallory Resort and Marina
Key West
135 reviews
Apartments with kitchens, two pools, and marina access in Key West
Check availabilityWhy guests love itCoconut Mallory Resort and Marina is built for families who need more room than a standard hotel room gives. The apartments come with fully equipped kitchens and private balconies, so breakfast and quiet evenings stay simple. Two outdoor pools and a hot tub keep the downtime varied, and the on-site bicycle and water sports rentals make it easy to get moving without arranging anything beforehand. Direct access to Coconut Mallory Marina is a plus for anyone drawn to the water around Key West.
Winslow's Bungalows - Key West Historic Inns
Key West
1,236 reviews
Historic bungalows with three pools and lush gardens in Key West
Check availabilityWhy guests love itWinslow's Bungalows has three swimming pools, so children rarely have to share a busy one, and the landscaped gardens are full of hammocks and swings. A continental breakfast is included each morning, and every room has a small refrigerator for drinks and snacks. Duval Street and the Southernmost Point are within walking distance, which makes evenings and photo stops easy without a car. Pets are welcome, so the family dog can join the trip.
Lighthouse Hotel - Key West Historic Inns
Key West
630 reviews
Historic Key West hotel with a heated pool and poolside bar
Check availabilityWhy guests love itI would choose the Lighthouse Hotel for a Key West stay in a historic building with a pool. It sits opposite the Ernest Hemingway Home and Museum, and guests rate it 8.4 across 630 reviews, a score I trust. An outdoor heated pool and a poolside bar are on site, a complimentary continental breakfast is included, and rooms have free WiFi and private bathrooms. Bicycle rentals are available, and pets are welcome.
Hampton Inn Key West FL
Key West
1,240 reviews
Heated pool with ocean views and a complimentary breakfast
Check availabilityWhy guests love itI would point families here for the heated pool with ocean views, which keeps children happy on days when the beach feels like too much effort. The free buffet breakfast each morning and the shuttle to Key West Airport remove two small logistical headaches. Rooms come with a microwave and a small refrigerator, handy for snacks and milk, and some have a balcony. Pets are accepted, and the poolside restaurant keeps dinner simple.
The Saint Hotel Key West, Autograph Collection, Adult Only
Key West
40 reviews
Adult-only hotel with balconies, a pool, and free bikes in Key West
Check availabilityWhy guests love itI have to be clear for families: The Saint Hotel is an adults-only property in central Key West, so it does not take children. For a couples' trip or an adult family getaway, guests rate it 8.3 across 40 reviews. Rooms are air-conditioned with balconies, the outdoor swimming pool is open all year beside a sun terrace, and bicycles are free to borrow. An American restaurant, a bar and a fitness centre are on site.
Courtyard by Marriott Key West Waterfront
Key West
372 reviews
Beachfront hotel with a heated pool and hot tub on the Gulf of Mexico
Check availabilityWhy guests love itIts waterfront setting on the Gulf side of Key West is what families will notice first, along with an outdoor heated pool and a hot tub for evenings back at the hotel. Laundry facilities help after beach days, the 24-hour reception handles late arrivals, and rooms include free WiFi, cable TV and coffee facilities. A fitness center is on site. Guests rate it 8.2 out of 10 from 372 reviews, and I would book it for a relaxed island stay.
Classic King Balcony at the James House
Key West
18 reviews
City-centre inn with balconies, a pool, and pet-friendly rooms
Check availabilityWhy guests love itI would choose this Classic King Balcony room at The James House for a couple or a small family that wants a central inn in Key West. Guests rate it 7.9 across 18 reviews. Rooms have private entrances, city-view balconies, air-conditioning, a refrigerator and a washing machine, which is handy after beach days. An outdoor swimming pool and a garden are on site, and local attractions are close by.
Green Room at the Grand Maloney
Key West
13 reviews
Air-conditioned rooms with private patios and an outdoor pool in Key West
Check availabilityWhy guests love itI would pick The Green Room at the Grand Maloney for a couple or a small family that wants to walk everywhere in Key West. Guests rate it 7.8 across 13 reviews. Rooms are air-conditioned with private entrances, a patio and city views, and the inn has an outdoor swimming pool and a garden. Simonton Street Beach and Mallory Square are within walking distance, and WiFi is free throughout.
Curry House- 3rd Floor, King Bed, & Balcony Room 8
Key West
9 reviews
King bed aparthotel with balcony, pool, and sun terrace in Key West
Check availabilityWhy guests love itAn outdoor swimming pool, a sun terrace and a garden are the shared spaces at Curry House in Key West, where Room 8 sits on the third floor with a king bed and a private balcony. Free WiFi, air conditioning and a private entrance are included. With one king bed, the room suits a couple or a parent with a small child rather than a family of four, and the 7.4 rating from only nine reviews gives little to go on, so I would keep expectations simple.
Local tips
- 1For a December to February trip, choose a heated pool, such as those at Orchid Key Inn, Ella's Cottages or Lighthouse Hotel.
- 2Want several pools on site? Simonton Court has four, Winslow's Bungalows three, and The Gardens Hotel and Coconut Mallory two each.
- 3Many Old Town inns on this list are adults-only, so check the age policy before booking with children.
- 4Travelling with a dog? Winslow's Bungalows, The Palms Hotel, Ella's Cottages and Lighthouse Hotel are listed as pet-friendly.
- 5Arriving by air? Hampton Inn Key West FL runs a shuttle to Key West Airport.
- 6For an apartment with a full kitchen, look at Coconut Mallory Resort and Marina or Hyatt Vacation Club at Windward Pointe.