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Hotels with Swimming Pool in Islamorada

130 HOTELS IN AND AROUND ISLAMORADARanking can be influenced by the commissions we receive.
Cheeca Lodge & Spa main photo
Cheeca Lodge & Spa
Resort in Islamorada FLUS flag
8.5
Very Good
From $229
$
Pool
Pool Lap Lanes
Outdoor Pool
Nestled in the heart of the Florida Keys, Cheeca Lodge offers a tranquil escape with its oceanfront pool and lush tropical surroundings. Relax in a private cabana and sip on tropical cocktails.
Summary of reviews related to the 'Pool' category
Cheeca Lodge & Spa boasts multiple pools, including beachside pools and a pool by the spa which was described as quiet and nice. Some guests had negative experiences, such as the pools closing too early or being overcrowded with loud children. However, many others enjoyed the beautiful pool areas which offered plenty of space to relax and were complemented by amenities such as poolside showers and convenient food delivery. The pools were also praised for their high quality and lovely appearance with some guests noting the breathtaking views of the beach and dock. The hotel also had a separate adult pool for those seeking a more peaceful environment. While some guests encountered issues with cleanliness, most found the pool areas to be enjoyable and relaxing. Overall, Cheeca Lodge & Spa offers a variety of pool options to suit different preferences and provides a pleasant atmosphere for guests.
Amara Cay Resort main photo
Amara Cay Resort
Hotel in Islamorada FLUS flag
7.9
Good
From $238
$
Pool
Heated Pool
Outdoor Pool
This modern resort offers luxurious accommodation with blue-and-white clad rooms and suites. It is right on the beach and features a swimming pool, excellent eateries, and a range of watersports.
Summary of reviews related to the 'Pool' category
The guests of Amara Cay Resort seem to be thoroughly impressed with the pool area of the hotel. Many described it as amazing, wonderful and beautiful. Some guests even mentioned the pool as the highlight of their stay. They loved the pool games, the tiki bar and the firepit area. The views from the pool were breathtaking and relaxing. Guests also enjoyed using the kayaks and attending the yoga classes on site. Although some guests mentioned that the pool could have been warmer, the majority spoke highly of the heated pool. The shallow end with lounge chairs that slope into the deep end was a hit among guests. The pool area was so pretty and inviting that some guests even forgave the hotel's non-smoking policy for the tiki bar and pool area. The outdoor facility and communal areas were also highly appreciated with many mentioning the grounds, the tiki bar and the firepit area. The hotel's sister property has a nice beach, although some guests described the hotel's beach as relaxing but not a real beach. Overall, the pool area made guests' stay enjoyable and memorable.
La Siesta Resort & Villas main photo
La Siesta Resort & Villas
Hotel in Islamorada FLUS flag
8.2
Very Good
From $189
$
Pool
Heated Pool
Outdoor Pool
The resort features multiple pools, including a large family pool and a smaller, quieter pool for relaxation. Guests appreciate the spacious pool areas and the lush landscaping.
Summary of reviews related to the 'Pool' category
La Siesta Resort & Villas offers a pool experience that stands out as a highlight for many guests. The swimming pool is often described as fabulous, incredible, and beautiful, with features catering to everyone, including families and kids. Its zero-entry design is particularly praised for its accessibility and suitability for younger children. The pool is not only heated but remains comfortable and inviting even in hot weather, contributing to a relaxing atmosphere.

The pool area is characterized by a clean and well-maintained environment, with a chilled atmosphere that many find inviting. Guests enjoy the convenience of amenities such as free pool towels and a tiki bar, and the friendly staff add to the overall pleasant experience. Beautiful views from the pool area enhance the enjoyment, offering opportunities to appreciate the lush landscaping and the scenic oceanfront. Although some mention occasional closures, the overall maintenance and cleanliness of the pool remain impressive.

La Siesta Resort & Villas complements the excellent pool with access to exciting ocean activities like kayaking and biking, adding to the recreational options available. While the beach area is primarily a boat dock, the stunning property with its great amenities more than compensates, making it a wonderful destination for relaxation and leisure.
Islander Resort main photo
Islander Resort
Resort in Islamorada FLUS flag
8.8
Excellent
From $252
$
Pool
Heated Pool
Outdoor Pool
The Islander Resort offers two distinct pool areas: a family-friendly pool with activities and a more secluded pool for quiet relaxation. Both pools are well-maintained and offer ample seating.
Summary of reviews related to the 'Pool' category
The pools at the Islander Resort are a standout feature that guests rave about. With a mix of saltwater and heated pools, guests can enjoy a variety of options. The pools are in close proximity to the ocean, providing beautiful views and beach access. The area surrounding the two pools is recently renovated with plenty of beach chairs and comfortable seating for guests to enjoy. Some reviewers note that supervision of the pool area could be improved. However, those seeking an adults-only experience can enjoy a separate pool. The pool side amenities and pool bars add to the experience. Overall, the pools are a well-loved aspect of this sprawling resort with beautiful views and beach area.
Chesapeake Beach Resort main photo
Chesapeake Beach Resort
Resort in Islamorada FLUS flag
8.5
Very Good
From $213
$
Pool
Heated Pool
Outdoor Pool
This resort features a large, heated pool with plenty of space for swimming and lounging. The pool area is surrounded by tropical foliage, creating a relaxing atmosphere.
Summary of reviews related to the 'Pool' category
At Chesapeake Beach Resort, guests frequently praise the presence of two fantastic swimming pools and a hot tub, which add to the appeal of this seaside haven. The pools are described as very nice, beautiful and appealing, offering a satisfactory depth suitable for children aged six and up. Many visitors appreciate the cleanliness and maintenance of the pools, noting that they are well-looked after and inviting. Free sun loungers enhance the poolside experience, providing a comfortable space for relaxation. While some reviews suggest the pools could be cleaner, the general consensus is overwhelmingly positive. A saltwater pool is an added bonus, heightening the unique amenities available. The pool areas, combined with ocean frontage and a charming little beach, make for a delightful stay. Additional facilities, such as a tiki bar and heated tub, contribute to the overall great experience. Despite some minor criticisms, the pools at Chesapeake Beach Resort remain a standout feature for many guests.
Pines & Palms Resort main photo
Pines & Palms Resort
Resort in Islamorada FLUS flag
9.3
Excellent
From $198
$
Pool
Heated Pool
Outdoor Pool
The resort offers a pool with ocean views and a private beach. Guests enjoy the tranquility and the well-kept pool area.
Summary of reviews related to the 'Pool' category
The pool at Pines & Palms Resort is a highlight for many guests with numerous positive comments about its warm water, cleanliness and well-maintained grounds. Guests appreciate the natural shade surrounding the pool and the opportunity to enjoy both kayaking and live music at the poolside bar. The pool overlooks the ocean, offering a great view and there are multiple docks and a sun lounge area for guests to enjoy. Some guests note that the pool is small or the poolside furniture is plastic, but overall guests enjoy spending time at this relaxed, key-feeling resort with a nice pool and friendly staff.
Questionnaire
Location of the pool:Outdoor pool
Is it a pool of special type?
Heated pool
When is the pool open?All year
Lime Tree Bay Resort main photo
Lime Tree Bay Resort
Resort in Islamorada FLUS flag
8.7
Very Good
From $195
$
Pool
Outdoor Pool
Lime Tree Bay Resort includes a relaxing pool area surrounded by native trees. The pool provides a serene escape for guests.
Summary of reviews related to the 'Pool' category
The pool area at Lime Tree Bay Resort receives high praise from guests, particularly for its cleanliness, aesthetic appeal and amenities. Described as amazing, wonderful and beautiful, the pool areas are clean, well-maintained and expansive, offering plenty of loungers and hammocks for relaxation. Several reviews highlight the pleasant and stunning nature of the pool area, often emphasizing features like heated options and picturesque views by the sea. The pools are noted for their kid-friendly aspects and come with added conveniences like snack services and nearby activities such as kayaking.

Despite these positives, some guests did comment on the smaller size of the pools with suggestions for more seating and larger towels. A few reviews mentioned maintenance issues, such as the pool heater not working and occasional cleanliness concerns, but overall, guests found the pool experience to be enjoyable and even described it as the best outdoor pool experience ever. The pool area also offers a tranquil setting with some areas being newly renovated and exclusive pools available for private use.

In summary, while there are a few minor concerns, the pool facilities at
Lime Tree Bay Resort largely contribute to a relaxing and enjoyable stay, characterized by clean, lovely and well-kept swimming spaces perfect for both adults and children.
Ragged Edge Resort & Marina main photo
Ragged Edge Resort & Marina
Resort in Islamorada FLUS flag
9.0
Excellent
From $191
$
Pool
Heated Pool
Outdoor Pool
The resort has a waterfront pool with views of the marina. It's a great spot for enjoying the scenery while taking a dip.
Caloosa Cove Resort by CoolVacay main photo
Caloosa Cove Resort by CoolVacay
Hotel in Islamorada FLUS flag
8.8
Excellent
From $253
$
Pool
Heated Pool
Outdoor Pool
Caloosa Cove Resort provides an outdoor pool for guests to enjoy. The pool area is well-maintained and offers a comfortable place to unwind.
Summary of reviews related to the 'Pool' category
Caloosa Cove Resort offers an impressive pool experience that consistently delights its guests. Strategically positioned overlooking the beach, the pool area presents a magnificent setting with stunning views. Guests rave about the pool's cleanliness and warmth, emphasizing how well-maintained and inviting it is. The size of the pool is adequate for a comfortable swim, accommodating both families and children who particularly enjoy the space. The adjacent deck complements the area perfectly, providing an ideal spot for relaxation and taking in the seaside scenery.

Guests frequently highlight the direct beach access, making it effortless to transition from the pool to the oceanfront. The resort ensures the pool remains open until midnight, which is a pleasant surprise for night owls wanting a late swim under a starlit sky. Parents appreciate the child-friendly features, making the pool an enjoyable destination for the entire family. The pool is consistently praised as outstanding, with its beautiful surroundings and fantastic views contributing greatly to the overall resort experience.
Fisher Inn Resort & Marina main photo
Fisher Inn Resort & Marina
Hotel in Islamorada FLUS flag
7.8
Good
From $135
$
Pool
Heated Pool
Outdoor Pool
This resort features a pool and a private beach, providing options for water activities. The pool area is clean and inviting.
Summary of reviews related to the 'Pool' category
Set against a backdrop of the sea, the swimming pool at Fisher Inn Resort & Marina offers mixed experiences for guests. On the positive side, the pool is praised for its nice location and modern appearance, benefiting from sea views and an array of clean beach towels available at all times. Families appreciate the heated pool, kayak rentals nearby and outdoor amenities that engage children.

However, some aspects leave room for improvement. Several guests have noted that the pool is small, which can lead to overcrowding, especially when larger groups gather. Maintenance and cleanliness seem inconsistent with reports of a cloudy, dirty and outdated pool that sometimes required more chemical balancing. On hotter days, the heated pool can become uncomfortably warm, adding to discomfort.

While the outdoor area is appreciated and the pool itself is generally liked for its convenience and temperature, addressing these maintenance and size issues could significantly enhance the overall guest experience.
Breezy Palms Resort main photo
Breezy Palms Resort
Hotel in Islamorada FLUS flag
8.2
Very Good
From $119
$
Pool
Outdoor Pool
Breezy Palms Resort has an outdoor pool for guests. The pool is a great place to cool off and relax during your stay.
Summary of reviews related to the 'Pool' category
Visitors to the Breezy Palms Resort have consistently praised the pool facilities, noting their cleanliness and well-maintained condition. Despite being on the smaller side, the pool is described as extremely nice and decently sized, making it accessible and convenient for guests. Families, particularly those with children, found the pool area enjoyable and comfortable for lounging. The pool temperature was often mentioned as perfect, further enhancing the overall experience.

The resort offers prompt and responsive service around the pool areas, which are equipped with necessary amenities such as loungers and towels. Additionally, the poolside is highly maintained with some guests highlighting it as one of the best in the region.

While the pool closes relatively early and some guests felt that the area could use a bit of modernizing, these points did not detract significantly from their positive experiences. The pool's location is also convenient, situated near open spaces and providing access to the resort’s marina and beach, which adds to the overall appeal of this tranquil setting.

In sum, the
Breezy Palms Resort's pool area has garnered favorable feedback for being clean, family-friendly and well-maintained, making it a significant highlight for guests staying at the resort.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort main photo
From $408
$
Pool
Heated Pool
Outdoor Pool
Summary of reviews related to the 'Pool' category
The pool experience at Postcard Inn Beach Resort & Marina has received mixed feedback from guests. Positively noted features include the pool's cleanliness at times, its oceanfront setting and the ample sunshine and plenty of pool chairs. Guests appreciated the well-maintained pool, beautiful swimming area and the convenience of multiple pools, along with the presence of a swim-up bar and tiki bar, although service at the pool bar was reported to be slow.

However, several areas were highlighted for improvement. Cleanliness was a recurring issue with some guests mentioning mold, leaves and insects in the pool. There were also reports of broken umbrellas, pool chairs and tiles falling. The need for pool renovations and the presence of cloudy and murky water were noted. Additionally, pool closures for repairs and maintenance disrupted the guest experience. The lack of pool towels and a non-functional pool lift chair were also points of concern.

Overall, while the pool area is considered lovely and enjoyable by many, some aspects clearly require attention to enhance the overall guest experience.
Coconut Cove Resort & Marina main photo
Coconut Cove Resort & Marina
Inn in Islamorada FLUS flag
8.1
Very Good
From $186
$
Pool
Outdoor Pool
The resort offers an outdoor swimming pool, fitness center and a shared lounge. The location is perfect and the pool is loved by the guests.
Summary of reviews related to the 'Pool' category
The pool at Coconut Cove Resort & Marina has garnered rave reviews from guests who appreciate both its aesthetic appeal and convenience. Open 24/7, the pool stands out for offering flexibility that few other resorts match, making it ideal for late-night or early-morning swims. Visitors frequently comment on its lovely shape and ample size, contributing to the overall positive poolside experience. The combination of beach and pool areas is consistently praised, creating an inviting atmosphere that complements its beachfront location. Various amenities surrounding the pool—such as a fire pit, ping-pong table, and gym—enhance the resort experience, while easy access to the Atlantic Ocean adds yet another dimension of allure. Overall, guests describe the pool as great, fabulous, and super spectacular, reinforcing its status as a key highlight of any stay at the resort.
Sunset Inn main photo
Sunset Inn
Hotel in Islamorada FLUS flag
8.5
Very Good
From $118
$
Pool
Outdoor Pool
This Inn features an outdoor pool. Guests enjoy the relaxed atmosphere of the pool area.
Summary of reviews related to the 'Pool' category
Sunset Inn boasts a truly beautiful pool area that receives consistent praise from guests. The pool itself is described as amazing, delightful and particularly inviting, making it a perfect spot for relaxation. Visitors appreciate the spaciousness of both the rooms and the outdoor areas, noting that the pool is clean and well-maintained.

The heated aspect of the pool is frequently highlighted, providing a warm and refreshing experience. It's large, lovely and enjoys great sunlight, which makes lounging by the pool a comfortable and pleasant activity. Families especially value the pool, finding it both entertaining and suitable for children. The pool area stays open late, adding to its convenience and appeal.

The surrounding courtyard and outdoor areas are equally well-received, offering a picturesque and relaxing environment. The location of
Sunset Inn is advantageous for those looking to explore the Keys with notable attractions like the restaurant Lorelei within walking distance.

Overall, the pool at
Sunset Inn is an appreciated and well-loved feature, offering guests a clean, inviting and relaxing retreat.
The Islands of Islamorada main photo
The Islands of Islamorada
Hotel in Islamorada FLUS flag
9.2
Excellent
$
Pool
Outdoor Pool
This hotel features an outdoor pool. Guests enjoy the relaxed atmosphere of the pool area.
Matecumbe Resort main photo
Matecumbe Resort
Aparthotel in Islamorada FLUS flag
8.5
Very Good
From $141
$
Pool
Heated Pool
Outdoor Pool
This aparthotel features an outdoor pool. Guests enjoy the relaxed atmosphere of the pool area.
Summary of reviews related to the 'Pool' category
Matecumbe Resort offers a variety of appealing features, particularly when it comes to its pool area. Guests consistently highlight the pool as a central attraction, noting its cleanliness and the availability of plenty of water toys. The heated pool is praised for being large, accommodating, and suitable for children, with an array of floats and noodles available for added fun. The pool area is well-maintained and provides great access to the sea, offering a tranquil environment that is both quiet and inviting. The resort's provision of additional amenities such as kayaks, bikes, and shuffleboard enhances the experience, making it a popular spot for families and individuals seeking both relaxation and a bit of adventure. Although some guests have mentioned the pool being crowded at times, the atmosphere remains pleasant and respectful. Overall, the pool at Matecumbe Resort stands out as a significant draw, contributing to the resort's appeal located in a serene and beautiful setting.
Drop Anchor Resort & Marina main photo
Drop Anchor Resort & Marina
Resort in Islamorada FLUS flag
7.9
Good
From $135
$
Pool
Heated Pool
Outdoor Pool
This resort features an outdoor pool. Guests enjoy the relaxed atmosphere of the pool area.
Summary of reviews related to the 'Pool' category
At Drop Anchor Resort & Marina, guests consistently highlight the delightful swimming pool as a standout feature of their stay. Described as both awesome and fantastic, the pool is praised for its warmth, offering the perfect respite from the sweltering heat. The resort's location enhances the pool experience, with loungers and hammocks providing a tranquil setting by the sea. Visitors are charmed by the pool area's cute design, complemented by hammocks and beach chairs that foster relaxation. The pool is located to offer stunning views, enabling guests to bask in the beauty of sunsets while enjoying the comfortable lawn furniture. Additionally, the availability of kayaks adds to the appeal, offering guests a chance for adventure right from the hotel's waterfront. Though some mention a language barrier with the staff, the friendliness and helpfulness of the team enhance the overall poolside experience.
Casa Morada main photo
Casa Morada
Hotel in Islamorada FLUS flag
8.9
Excellent
$
Pool
Casa Morada offers a serene pool area with lush landscaping, providing a tranquil escape for guests.
Hadley Resort and Marina main photo
Hadley Resort and Marina
Hotel in Islamorada FLUS flag
7.3
Good
From $150
$
Pool
Outdoor Pool
This resort features an outdoor pool. Guests enjoy the relaxed atmosphere of the pool area.
Summary of reviews related to the 'Pool' category
Nestled in a prime location, Hadley Resort and Marina offers a pool area that receives mixed reviews from guests. Visitors frequently highlight the pool area for being clean and well-maintained with a comfortable setting that many find enjoyable and pleasant. The pool's proximity to guest accommodations is another positive feature, making it easily accessible for those wishing to take a quick dip.

However, the pool is often mentioned as being very small, which can be a disappointment, especially given the more spacious appearance in promotional photos. Some guests also noted variability in water temperature, at times finding it very cold, while others described it as warm. There were also occasional comments about cleanliness issues, including floating bugs and clumps of hair, which some found off-putting.

Despite these points, the pool area remains a quiet and relaxing place for guests to unwind, often found to be empty or sparsely populated, offering a bit of solitude. The lack of additional poolside amenities such as a jacuzzi, bar or plentiful lounge chairs could be a downside for those looking for a more comprehensive poolside experience.

Overall, while the pool area at
Hadley Resort and Marina has some drawbacks, particularly regarding size and occasional cleanliness, many guests appreciate its cleanliness, convenience and the comfortable setting it offers.
La Jolla Resort main photo
La Jolla Resort
Inn in Islamorada FLUS flag
8.8
Excellent
From $154
$
Pool
Outdoor Pool
This resort features an outdoor pool. Guests enjoy the relaxed atmosphere of the pool area.
Summary of reviews related to the 'Pool' category
Guests at La Jolla Resort give mixed reviews about the pool with many appreciating its cleanliness and the beautiful surroundings, including lovely grounds filled with palm trees and tropical plants. Despite its small size, several guests found the pool sufficient and enjoyable for a quick dip, particularly as a fun alternative for children when the sea is rough. The availability of poolside activities like kayaks and paddleboards also added to the positive experience for some visitors.

However, there were a few critiques. The pool's location near the highway was frequently mentioned, leading to noise and a less relaxing atmosphere for those seeking tranquility. Additionally, some guests noted that the pool was cold or too warm and occasionally cloudy or dirty, which detracted from their enjoyment. The absence of heating and issues like weeds at the bottom as one dips in seemed to affect the overall satisfaction for some guests. Despite these drawbacks, many visitors still considered the pool a usable and nice facility amidst their stay.
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 130 hotels in and around Islamorada
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