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Hotels with Outdoor Pool in Islamorada

94 HOTELS IN AND AROUND ISLAMORADARanking can be influenced by the commissions we receive.
Islander Resort main photo
Islander Resort
Resort in Islamorada FLUS flag
8.8
Excellent
From $252
$
+4
Outdoor Pool
Islander Resort blends coastal charm with sleek interiors, offering beachfront dining and saltwater pools. Guests can enjoy activities ranging from snorkeling to bocce ball, with beachfront access and a fishing pier for year-round enjoyment.
Cheeca Lodge & Spa main photo
Cheeca Lodge & Spa
Resort in Islamorada FLUS flag
8.5
Very Good
From $229
$
+1
Outdoor Pool
Cheeca Lodge & Spa offers a luxurious experience with 27 acres of oceanfront property. It features multiple pools, a 9-hole golf course, a spa, and diverse activities like fishing from a 525-foot pier, kayaking, and various water sports, ensuring a comprehensive resort experience.
Summary of reviews related to the 'Outdoor Pool' category
Cheeca Lodge & Spa boasts multiple outdoor pool areas that guests have raved about in their reviews. The pool areas are all stunning and offer beautiful views of the dock and beach while providing a relaxing atmosphere. Many guests have enjoyed their comfortable and spacious rooms which include necessary appliances and stunning bathrooms, such as ones with soaking tubs on private patios. The hotel also offers a range of amenities that guests can take advantage of even after checking out. Among the many pools, there is an adult pool, ensuring guests can enjoy a quiet and peaceful swim. Overall, guests have enjoyed a wonderful stay at the hotel and the nice pools and amenities have only enhanced their experience.
Amara Cay Resort main photo
Amara Cay Resort
Hotel in Islamorada FLUS flag
8.0
Very Good
From $238
$
+4
Info
Summary of reviews
Amara Cay Resort is a beautiful and tropical getaway located in Islamorada with a stunning beachfront location that offers breathtaking views and a perfect spot to watch the sunrise. The resort is close to everything with plenty of great places to eat and explore in the area and it offers a free shuttle to get around Islamorada. The pool, beach, dock and outdoor activities like diving and fishing make Amara Cay Resort a popular choice. The breakfast is excellent with guests raving about the quality and taste of the morning meal and the dinner is also highly recommended with the fish tacos being particularly flavorful. The hotel rooms are modern, updated and spacious with beautiful ocean views and the hotel interior is immaculately clean. The staff is exceptional, providing excellent customer service and making guests feel welcome. The pool area is amazing with a heated pool, pool games, tiki bar and firepit area and the beach area is nice with available rentals and recommendations for outdoor activities like kayaking. Amara Cay Resort is a great option for families looking for a fun and relaxing vacation and it offers a very nice and relaxing atmosphere with pleasant facilities. While some guests found the prices to be a bit expensive, overall the stay was worth it.
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Beachfront
La Siesta Resort & Villas main photo
La Siesta Resort & Villas
Hotel in Islamorada FLUS flag
8.2
Very Good
From $189
$
+6
Info
Summary of reviews
La Siesta Resort & Villas in Islamorada is highly praised for its extraordinary location, nestled amidst the breathtaking surroundings of the Florida Keys. Guests enjoy the resort's stunning beachfront setting with direct access to water activities, making it an ideal retreat for both relaxation and adventure. The property is conveniently close to local attractions, restaurants, and shops, ensuring a perfect balance of tranquility and accessibility.

The resort stands out for its warm, family-friendly atmosphere, with spacious, clean accommodations that cater to families and large groups. Guests appreciate the layout, which often includes separate living areas, kitchenettes, and beautiful ocean or garden views. The staff are commended for their exceptional service, known for their friendliness and willingness to make guests feel at home.

The resort's amenities contribute significantly to the relaxing experience, especially the incredible pool area, which is perfect for families with its zero-entry design and comfortable environment. Although the breakfast offerings are basic, they are convenient, and guests often supplement with visits to local eateries like the Midway Café. The beach, while smaller, is clean and peaceful, providing a serene spot for sunbathing and kayaking.

La Siesta Resort & Villas takes pride in its cleanliness, with well-maintained grounds and inviting poolside amenities. Although there are minor issues with WiFi consistency and room updates, these do not overshadow the positive experience overall. Parking is easy and convenient, especially for those with boats.

Guests find the beds particularly comfortable, contributing to restful stays. The resort is also celebrated for being dog-friendly, making it an inclusive destination for those traveling with pets. With its blend of luxury, charming atmosphere, and access to facilities across sister properties, La Siesta offers a subtle yet luxurious experience.

Guests often leave with fond memories, looking forward to returning, making it a cherished destination for families, couples, and individuals seeking relaxation in a picturesque tropical setting.
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Luxury
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort main photo
From $408
$
+2
Outdoor Pool
Three Waters Resort and Marina offers a reimagined island escape with oceanfront access. It provides multiple pools and dining options, focusing on unparalleled service and a perfect Florida Keys getaway.
Summary of reviews related to the 'Outdoor Pool' category
The outdoor pool area at Postcard Inn Beach Resort & Marina receives high praise for its inviting ambiance and well-maintained facilities. Guests highlight the beautiful and relaxing environment, complemented by plenty of palm trees and ample pool chairs. The pool is often described as clean and secluded, providing a perfect spot for relaxation. The swim-up bar and pool bar receive particular commendation, adding to the overall enjoyment with amazing service and a pleasant atmosphere. Live music at the pool site enhances the experience. Though there are mixed mentions about the heating of the pool with some indicating it's heated and others noting it is not, the setting remains delightful overall. The outdoor area's beauty and the quality of the pool are frequently mentioned, making it a standout feature of the resort.
Pines & Palms Resort main photo
Pines & Palms Resort
Resort in Islamorada FLUS flag
9.3
Excellent
From $198
$
+3
Outdoor Pool
Questionnaire
Location of the pool:Outdoor pool
Is it a pool of special type?
Heated pool
When is the pool open?All year
Coconut Cove Resort & Marina main photo
Coconut Cove Resort & Marina
Inn in Islamorada FLUS flag
8.3
Very Good
From $186
$
+3
Info
Summary of reviews
Coconut Cove Resort & Marina, situated at the heart of the Florida Keys, offers an idyllic retreat characterized by its breathtaking ocean vistas and serene surroundings. Its strategic location allows guests to enjoy stunning waterfront views while remaining conveniently close to local restaurants, bars, and attractions. Despite a lack of direct beach access, the resort's sandy areas provide ample relaxation opportunities, and its proximity to Key West adds to its appeal as a base for exploring the region.

While the grab-and-go breakfast could benefit from a broader range of choices, the resort excels in offering charming accommodations in its clean and cozy cottages. These rooms are well-appointed with kitchenettes and are generally praised for their comfort and cleanliness, though some parts of the facilities could use updating. The grounds of the resort are meticulously maintained, creating a picturesque and welcoming environment that enhances the overall experience. Beautiful views, especially at sunrise, coupled with the fresh aroma throughout the property, are frequently highlighted by guests.

The standout feature of Coconut Cove is its dedicated and friendly staff, who are often lauded for their helpfulness and warm hospitality. The front desk receives particular praise for its excellent service, contributing significantly to the positive guest experience.

Another highlight of the resort is its pool, open 24/7, which combined with the beach area, offers an inviting atmosphere for relaxation. Guests frequently comment on the pool's unique charm and the range of amenities, including a fire pit, ping-pong table, and gym, that enhance the resort’s appeal. With easy access to the Atlantic Ocean, the pool area is considered a key highlight for visitors seeking leisure and enjoyment.

Overall,
Coconut Cove Resort & Marina offers a tranquil and beautiful setting for a relaxing getaway, with minor areas for improvement overshadowed by its strengths in location, service, and amenities.
Categories
Outdoor Pool
Pool
Outdoor Pool
Accessible
Breezy Palms Resort main photo
Breezy Palms Resort
Hotel in Islamorada FLUS flag
8.2
Very Good
From $119
$
+1
Outdoor Pool
Breezy Palms Resort offers beachfront accommodation with an outdoor swimming pool and a private beach area. Guests can enjoy the terrace and the convenience of being located on the beachfront.
Summary of reviews related to the 'Outdoor Pool' category
The outdoor pool at Breezy Palms Resort is a highlight for guests, consistently described as clean and well-maintained. It offers open spaces and is accessible 24/7, making it convenient for any time of day. The pool area is nicely landscaped and provides a comfortable and relaxing environment. It's evident that families particularly enjoy the pool, which is noted to be of a decent size with a perfect temperature for swimming. Guests appreciate having rooms with direct pool access, enhancing the convenience and enjoyment of their stay. Despite occasional weather-related usability issues, the pool remains a remarkable feature of the resort with its heated option ensuring comfort in cooler conditions. Overall, the pool, along with the attractive pier and pleasant beach area, contributes significantly to the positive experience at Breezy Palms Resort.
Lime Tree Bay Resort main photo
Lime Tree Bay Resort
Resort in Islamorada FLUS flag
8.7
Very Good
From $195
$
Outdoor Pool
Lime Tree Bay Resort is a relaxing resort with comfortable accommodations. It provides access to an outdoor pool and nearby water activities, ensuring a pleasant stay.
Summary of reviews related to the 'Outdoor Pool' category
Lime Tree Bay Resort offers a welcoming outdoor pool that guests consistently praise for being clean and spacious. Descriptions of the pool area highlight its beauty and well-maintained condition. Many guests found lounging by the pool magical, enhanced by plenty of loungers and hammocks available for relaxation. The pool is conveniently situated with a view of the ocean, which adds to the serene atmosphere.

While some mentioned that the pool is small, others noted its spaciousness, reflecting varied perspectives. The pool area is also described as lovely and public spaces are commended for their pleasant setup. The heated pools are appreciated, though a few guests pointed out occasional maintenance needs.

In addition to the pool, the resort provides a variety of water sports equipment, including paddleboards, kayaks and bicycles, at no extra cost, adding to the outdoor fun. There's also a dock and a beautiful open beach that contribute to the resort’s charm.

Overall, the outdoor pool at
Lime Tree Bay Resort is seen as a wonderful and refreshing amenity that significantly enhances the guest experience.
Chesapeake Beach Resort main photo
Chesapeake Beach Resort
Resort in Islamorada FLUS flag
8.5
Very Good
From $213
$
+2
Outdoor Pool
Chesapeake Beach Resort provides a beachfront location with an outdoor pool. It offers a comfortable and relaxing stay with easy access to the beach.
Fisher Inn Resort & Marina main photo
Fisher Inn Resort & Marina
Hotel in Islamorada FLUS flag
7.7
Good
From $135
$
+1
Outdoor Pool
Summary of reviews related to the 'Outdoor Pool' category
Fisher Inn Resort & Marina offers a host of amenities centered around its outdoor pool, making it a standout feature for many guests. The pool is universally praised for being well-maintained and clean and its heated feature ensures that it remains enjoyable even on colder days. The surrounding area is equipped with a variety of recreational options such as kayaks, biking amenities and a playground, catering to both adults and children.

Guests appreciate the organized availability of these activities, adding to the convenience and enjoyment of their stay. The pool area, while sometimes crowded and accompanied by loud music, still receives commendations for its overall appeal. Though a few visitors noted that the area seemed a bit dilapidated at times and experienced issues such as algae on weekends, the general consensus remains positive.

This older yet seemingly recently updated resort manages to maintain a pleasant, clean and inviting atmosphere. The pool and hot tub area, in particular, are repeatedly described as great, lovely and wonderful. However, for those looking for a quieter experience, the crowd may be a minor drawback. Overall,
Fisher Inn Resort & Marina's outdoor pool continues to be a highlight for many of its visitors.
Sunset Inn main photo
Sunset Inn
Hotel in Islamorada FLUS flag
8.5
Very Good
From $118
$
+1
Outdoor Pool
Summary of reviews related to the 'Outdoor Pool' category
The Sunset Inn's outdoor pool consistently garners praise for its pleasant and inviting ambiance. Guests describe the pool as delightful, nicely heated and visually appealing. The surrounding facilities enhance the experience, featuring tables and chairs for dining, a ping pong table and a giant chess board. This creates a versatile and enjoyable environment for relaxation and activity. Access to an array of amenities, including the pool and bicycles, adds to the charm of this updated and fresh lodging choice.
La Jolla Resort main photo
La Jolla Resort
Inn in Islamorada FLUS flag
8.8
Excellent
From $154
$
Outdoor Pool
Summary of reviews related to the 'Outdoor Pool' category
Located in a prime spot, La Jolla Resort features an outdoor pool that, while small, is well-kept and perfect for cooling off. The pool's water temperature is often cited as just right. Though it might not accommodate many guests simultaneously, it is seen as adequate for children and provides a refreshing dip amidst the resort's well-maintained outdoor facilities. Seating around the pool is limited, so planning ahead might be necessary for lounging. For those seeking more extensive aquatic adventures, the resort offers free kayaks, allowing guests to enjoy paddling right from the property's dock.
Hadley Resort and Marina main photo
Hadley Resort and Marina
Hotel in Islamorada FLUS flag
7.2
Good
From $150
$
Outdoor Pool
Summary of reviews related to the 'Outdoor Pool' category
The outdoor pool at Hadley Resort and Marina stands out in a multitude of ways, offering a mix of experiences to guests. Many reviews highlight the pool as being nice, clean and well-maintained. The location of guest accommodations is conveniently close to the pool, making it easy to enjoy a refreshing dip or relax in the pleasant surroundings. The pool is described as a large outdoor area with a generally clean atmosphere and guests appreciate that it usually isn't crowded, providing a private pool experience.

However, it’s worth noting that some reviews mention the pool can be chilly and a few guests found it too cold for their liking. Despite the debate on water temperature, it appears that the pool is heated, which is a positive aspect for those who prefer a warmer experience. The size of the pool area receives mixed feedback with several guests describing it as small or very small.

Additional amenities around the pool, such as bean bags and pool towels, enhance the comfort of the space, though some guests have pointed out the absence of a shower. While there's no beach access directly from the resort, the pool area provides a nice spot to soak up some sunshine and enjoy the outdoor setting.

Overall, the pool at
Hadley Resort and Marina offers a predominantly positive experience with its cleanliness and convenience, despite some varying opinions on its size and temperature.
Drop Anchor Resort & Marina main photo
Drop Anchor Resort & Marina
Resort in Islamorada FLUS flag
7.9
Good
From $135
$
+6
Outdoor Pool
Drop Anchor Resort & Marina features an ocean-side outdoor swimming pool and is located near Windley Key Fossil Reef Geological State Park. It offers a convenient and relaxing stay.
The Islands of Islamorada main photo
The Islands of Islamorada
Hotel in Islamorada FLUS flag
9.2
Excellent
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Luxury
Caloosa Cove Resort by CoolVacay main photo
Caloosa Cove Resort by CoolVacay
Hotel in Islamorada FLUS flag
8.8
Excellent
From $253
$
+1
Outdoor Pool
Caloosa Cove Resort features an outdoor pool and sun terrace. It offers a peaceful stay with comfortable accommodations and friendly staff.
Ragged Edge Resort & Marina main photo
Ragged Edge Resort & Marina
Resort in Islamorada FLUS flag
9.1
Excellent
From $191
$
+3
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Parking
Bayside Villas by Islander Resort main photo
Bayside Villas by Islander Resort
Resort in Islamorada FLUS flag
8.6
Very Good
From $288
$
+9
Info
Categories
Outdoor Pool
Pool
Heated Pool
Panoramic View Pool
Outdoor Pool
Sustainability Journey
The Ocean View Inn main photo
The Ocean View Inn
Hotel in Islamorada FLUS flag
8.4
Very Good
$
+4
Info
Summary of reviews
The Ocean View Inn, located in the heart of Isla Morada, is a favored destination for travelers exploring the Florida Keys due to its convenient proximity to local attractions and the added bonus of a private dock for boaters. The hotel's atmosphere is elevated by friendly and professional staff, with particular praise for the manager, Cindy, and the bartenders, all of whom contribute to the welcoming and enjoyable environment.

Guests consistently laud the inn for its comfortable and well-appointed rooms, highlighting their cleanliness, spaciousness, and island-inspired decor. Many rooms offer private patios that connect to the inviting pool and bar area, providing a seamless blend of relaxation and local charm. The overall ambiance is one that promotes tranquility, making it an excellent choice for both short and extended stays.

The Inn's standout feature is its beautifully maintained pool, which guests often describe as a refreshing oasis. The pool area is thoughtfully equipped with lounge chairs, tables, and umbrellas, providing a perfect setting for relaxation. An outdoor shower adds convenience for beachgoers. Families especially appreciate the charming pool setting and the friendly service that enhances their stay.

While the cleanliness of the bar area could see improvement, the Inn consistently receives high marks for overall room cleanliness and maintenance.
The Ocean View Inn continues to be a popular choice for its inviting accommodations and warm hospitality, offering a delightful blend of natural beauty and attentive service to ensure a memorable visit.
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Beach
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 94 hotels in and around Islamorada
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