A beach with white lounge chairs, a covered pavilion, and palm trees.

Find Hotels with a Pool in Islamorada, FL

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Our top choices for Islamorada hotels with a pool

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,748 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
$197 nightly
The price is $221
Aug 17 - Aug 18
Total with taxes and fees
Chesapeake Beach Resort

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,342 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
$226 nightly
The price is $254
Aug 2 - Aug 3
Total with taxes and fees
Cheeca Lodge & Spa

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,076 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
$321 nightly
The price is $361
Aug 9 - Aug 10
Total with taxes and fees
Islander Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,291 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
$233 nightly
The price is $262
Aug 17 - Aug 18
Total with taxes and fees
Amara Cay Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (232 reviews)
  • cleanliness
    Sparkling pools welcome island adventurers to this oceanfront sanctuary with marina access and private beach lounging areas.
$272 nightly
The price is $306
Aug 10 - Aug 11
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
$237 nightly
The price is $266
Aug 20 - Aug 21
Total with taxes and fees
La Siesta Resort & Villas

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (452 reviews)
  • cleanliness
    Poolside paradise in the heart of Matecumbe beckons with loungers under shady umbrellas.
$316 nightly
The price is $356
Aug 13 - Aug 14
Total with taxes and fees
Bayside Villas by Islander Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,395 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
$179 nightly
The price is $201
Aug 16 - Aug 17
Total with taxes and fees
Lime Tree Bay Resort

The Caribbean Resort

The Caribbean Resort
3.5 star property
Matecumbe
10.0 out of 10, Exceptional, (174 reviews)
The Caribbean Resort

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,004 reviews)
  • cleanliness
    Dive into coastal bliss with a private beach, marina, and refreshing pool for aquatic adventures.
$145 nightly
The price is $163
Aug 2 - Aug 3
Total with taxes and fees
Hadley Resort and Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Islamorada

Hotels with pools and free breakfast in Islamorada

Hotels with pools and hot tubs in Islamorada

Top Islamorada Hotel Reviews

Frequently asked questions

How much does a hotel with outdoor pool in Islamorada cost?
Enjoy staying in a hotel in Islamorada with an outdoor pool. You can find a great deal from $135 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Islamorada that have private outdoor pools?
Cheeca Lodge & Spa is a stunning 5-star hotel located in the heart of Islamorada, offering an array of luxurious amenities that cater to travellers seeking both adventure and relaxation. With an impressive review score of 9.2, guests rave about the friendly and attentive staff, the beautiful and clean rooms, and the exceptional dining experiences.

One of the standout features of Cheeca Lodge is its private outdoor pool, which provides an exclusive retreat for guests looking to unwind. This serene environment is complemented by poolside cabanas and sun loungers, ensuring you can soak up the sun in style. Additionally, the resort's beachfront location allows for easy access to a private beach, making it superb for families and couples alike.

Whether you're enjoying a massage on the beach, indulging in 24-hour room service, or taking advantage of the resort's on-site tennis and golf facilities, Cheeca Lodge & Spa seamlessly blends luxury with the natural beauty of Florida.
What are some of the best Islamorada hotels with outdoor pools and scenic views?
The Caribbean Resort is a charming 3.5-star hotel that captivates guests with its stunning ocean views and an inviting outdoor pool, rated a great 10.0 by travellers. Families appreciate the helpful staff and beautifully clean rooms, making it a wonderful choice for those seeking both relaxation and adventure in Islamorada.

Another fantastic option is the Chesapeake Beach Resort, also rated 3.5 stars and earning an excellent score of 9.2. This hotel not only features a clean outdoor pool but also offers beautiful views of both the ocean and the beach. Guests rave about the friendly staff, comfortable rooms, and excellent complimentary breakfast, making it an ideal family getaway.

For a luxurious experience, consider the 5-star Cheeca Lodge & Spa, where you'll find an expansive outdoor pool along with private cabanas for a touch of elegance. With a review rating of 9.2, this resort is great for families looking to indulge. Guests praise the amazing amenities, beautiful rooms, and excellent dining options, ensuring a memorable stay for everyone.

The Pines & Palms Resort, a 3-star hotel with a cozy atmosphere, also boasts an outdoor pool with ocean views, rated at 9.2 by visitors. Families enjoy the beautiful location and clean rooms, great for unwinding after a day of adventure.

Lastly, the Islander Resort stands out with its 4-star rating and beautiful outdoor pool, accompanied by breathtaking ocean and beach views. With a score of 9.2, guests highlight the friendly staff and spacious, clean accommodations, making it an excellent choice for families seeking both adventure and comfort.
Are there hotels in Islamorada with outdoor pool cabanas or loungers?
The Cheeca Lodge & Spa is a renowned 5-star hotel in Islamorada, celebrated for its stunning outdoor pool area, complete with luxurious cabanas and sun loungers. Guests rave about the exceptional service, beautiful accommodations, and the serene atmosphere that makes it a great retreat for families and couples alike, earning it an impressive traveller rating of 9.2.

For a more casual vibe, the Sunset Inn, a charming 3-star option, offers an inviting outdoor pool with complimentary pool cabanas. Travellers appreciate its central location and friendly, helpful staff, making it a great choice for those seeking a warm and welcoming environment, reflected in its stellar review score of 9.4.

Another fantastic option is the Islander Resort, a 4-star property featuring both pool cabanas and sun loungers by the pool, which is described as beautiful and spacious. Guests enjoy the incredible service and well-kept facilities, securing a traveller rating of 9.2.

Lastly, Casa Morada, a 3.5-star hotel, boasts a lovely outdoor pool where you can relax on sun loungers, complemented by a poolside bar and complimentary breakfast options. With a review score of 9.4, this hotel is known for its excellent staff and comfortable accommodations, great for families seeking both fun and relaxation.
Which Islamorada hotels offer poolside service for food and drinks?
Casa Morada, a charming 3.5-star hotel, offers a delightful poolside bar that enhances your relaxation by serving refreshing drinks while you soak up the sun. Guests consistently rave about the comfortable rooms and the excellent service from the helpful staff, making it a top choice for those seeking a tranquil escape.

For a bit of luxury, Cheeca Lodge & Spa stands out as a 5-star gem in Islamorada. Not only does it feature an inviting poolside bar, but it also boasts private cabanas and a stunning beachfront location. With a stellar rating of 9.2, visitors appreciate the beautiful clean rooms and the friendly, attentive staff who go above and beyond to ensure a memorable stay.

Another great option is the Pines & Palms Resort, rated 9.2 by travellers. This 3-star resort also provides a poolside bar, allowing guests to enjoy snacks and beverages as they lounge by the outdoor pool. The beautiful surroundings and clean accommodations make it a lovely spot for travellers.

Islander Resort, a 4-star hotel, also features a poolside bar, where you can indulge in drinks while enjoying the beautiful ocean view. Guests frequently compliment the friendly service and the spacious, well-maintained pool area, contributing to a great family-friendly atmosphere.

Lastly, Amara Cay Resort, with an 8.8 rating, offers a welcoming poolside bar as well. Known for its beautiful outdoor pool and comfortable rooms, this 4-star resort provides a relaxing environment superb for unwinding after a day of exploration.
Are there hotels with outdoor pools that are close to MoradaWay Arts & Cultural District?
The Caribbean Resort is a charming 3.5-star hotel that features an inviting outdoor pool, great for families looking to unwind after a day of exploring. Guests rave about the beautiful, clean rooms and the helpful staff, earning this hotel a stellar rating of 10.0. Located nearby MoradaWay Arts & Cultural District, it provides easy access to local art and culture, making it an ideal choice for those who appreciate both leisure and exploration.

Another excellent option is the Sunset Inn, a cozy 3-star hotel boasting a warm outdoor pool and spacious, clean rooms. With a review rating of 9.4, travellers appreciate the friendly staff and the central location, which is great for venturing out to nearby attractions. Plus, the complimentary self-parking adds to the convenience for families traveling by car.

For a more upscale experience, Casa Morada, also a 3.5-star hotel, offers a resort-style outdoor pool along with free continental breakfast. Guests have praised the excellent and comfortable rooms, as well as the attentive staff, securing a review score of 9.4. Its proximity to the cultural district makes it a wonderful base for exploring the local art scene.

Lastly, if you're seeking a luxurious stay, consider Cheeca Lodge & Spa, a stunning 5-star resort that features a spectacular outdoor pool, private beach access, and a range of amenities including a poolside bar and tennis courts. With a review score of 9.2, guests consistently highlight the friendly service, beautiful accommodations, and delicious food, ensuring a memorable family getaway.
Are there hotels in Islamorada with outdoor pool activities or events?
Islamorada, known as the "Sport Fishing Capital of the World," is an idyllic destination that offers a variety of hotels with outdoor pool activities and events. This charming area is great for travellers looking to enjoy the sun, sea, and leisure in a tropical paradise.

Chesapeake Beach Resort stands out with its two inviting outdoor pools that boast breathtaking ocean views, setting the stage for both relaxation and social gatherings. The resort also features an oceanfront event venue, allowing guests to enjoy poolside events while soaking up the stunning scenery.

For families seeking a luxurious experience, Cheeca Lodge & Spa is an excellent choice. The resort offers a family-friendly pool area complete with a full-service watersports facility just a stone's throw away. Guests can reserve private cabanas at either the spa pool or infinity pool, creating a serene personal oasis where you can unwind and take in the beautiful surroundings.

Fisher Inn Resort & Marina is another fantastic option, featuring a heated outdoor pool that caters to comfort and enjoyment. With poolside amenities, including sun loungers and outdoor furniture, this resort encourages guests to bask in the warm Florida sun while enjoying a leisurely day by the water.
Is it cheaper to book flights and a Islamorada hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Islamorada for you.

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