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

Find Hotels with a Pool in Islamorada, FL from CA $132

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Check availability on Islamorada Hotels with a Pool

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Islamorada hotels with a pool

A tropical resort with a swimming pool, palm trees, and a waterfall.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,491 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is CA $225
CA $356 total
includes taxes & fees
Nov 1 - Nov 2
Cheeca Lodge & Spa
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,811 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is CA $197
CA $300 total
includes taxes & fees
Nov 9 - Nov 10
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,156 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is CA $262
CA $398 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
A resort pool with palm trees, beach chairs, and umbrellas.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,327 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is CA $221
CA $352 total
includes taxes & fees
Nov 18 - Nov 19
Amara Cay Resort
A resort with a pool, beach, and ocean view.

5. 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
9.2 out of 10, Wonderful, (303 reviews)
  • cleanliness
    Sparkling pools welcome island adventurers to this oceanfront sanctuary with marina access and private beach lounging areas.
The price is CA $335
CA $480 total
includes taxes & fees
Nov 3 - Nov 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A resort with a swimming pool, lounge chairs, and palm trees.

6. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,557 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is CA $174
CA $258 total
includes taxes & fees
Nov 2 - Nov 3
Lime Tree Bay Resort
A nighttime swimming pool with a blue tint, surrounded by palm trees and a fenced area with lounge chairs.

7. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is CA $97
CA $182 total
includes taxes & fees
Nov 3 - Nov 4
Breezy Palms Resort
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

8. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,004 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is CA $170
CA $237 total
includes taxes & fees
Oct 29 - Oct 30
Fisher Inn Resort & Marina
Exterior

9. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
  • cleanliness
    Poolside paradise in the heart of Matecumbe beckons with loungers under shady umbrellas.
The price is CA $309
CA $451 total
includes taxes & fees
Nov 4 - Nov 5
Bayside Villas by Islander Resort
A resort with a pool surrounded by palm trees and a view of the ocean.

10. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
The price is CA $217
CA $346 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
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.
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Choose what matters most at hotels with a pool in Islamorada

Breakfast included
4 stars

Hotels with pools and free breakfast in Islamorada

A beach with palm trees and lounge chairs.
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1811)
The price is CA $197
CA $300 total
includes taxes & fees
Nov 9 - Nov 10
Chesapeake Beach Resort
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4-star hotels with pools in Islamorada

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1156)
The price is CA $262
CA $398 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
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.
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Find out more about Islamorada

Discover top Islamorada attractions

Islamorada, known as the Fishing Capital of the World, offers travellers a blend of adventure and relaxation. Start your day by casting a line in the crystal-clear waters, where you can catch everything from tarpon to snapper—perfect for both novice and seasoned anglers alike. For those who prefer to stay dry, the vibrant coral reefs surrounding the area invite you to snorkel or dive among colorful marine life, providing an unforgettable underwater experience. As the sun sets, take a scenic drive along the stunning Overseas Highway, where panoramic views of the ocean and lush islands will leave you in awe. Don’t miss the opportunity to explore the local arts scene, with galleries showcasing the unique works of talented artists inspired by the beautiful surroundings. Finally, indulge in the local culinary delights, from fresh seafood to innovative cuisine, at charming eateries that resonate with the island's laid-back vibe. After a day of exploration, unwind in one of the area’s luxurious accommodations, where attentive service and quality amenities will ensure a pampering experience, making it easy for you to plan your next adventure in this tropical paradise.

Find the best pool hotels in Islamorada

For travellers seeking a refreshing escape in Islamorada, these hotels boast outstanding pool facilities, perfect for relaxation and fun in the sun. Dive into these top picks that cater to your love for pools.

The Islands of Islamorada

  • Why it's great: The Islands of Islamorada is a luxurious retreat that features an outdoor pool with a poolside bar, making it an excellent choice for pool lovers. With a perfect review rating of 10 out of 10 and a prestigious 5-star rating, travelers can indulge in an upscale experience that focuses on relaxation and enjoyment.
  • Other amenities: In addition to the beautiful pool area, the hotel offers a variety of amenities, including on-site spa services and massage options. Guests can enjoy beach access, complimentary beach towels, and a range of nearby water activities such as snorkeling and parasailing. The hotel also features free self-parking, air conditioning, and a concierge service for a seamless stay.
  • Neighborhood: Matecumbe
  • Nearby attractions: Keys History & Discovery Center - 1 km, History of Diving Museum - 1 km, Matecumbe United Methodist Church - 2 km

The Ocean View Inn & Pub

  • Why it's great: The Ocean View Inn & Pub is a charming option for those who appreciate poolside relaxation. This budget-friendly hotel boasts an accessible outdoor pool and has earned a review rating of 9 out of 10, making it a solid choice for travellers on a budget.
  • Other amenities: Guests will find daily housekeeping and complimentary toiletries to enhance their stay. The hotel also provides free Wi-Fi and self-parking for added convenience. With air conditioning and a patio for outdoor enjoyment, this inn offers a cozy atmosphere for a refreshing getaway.
  • Nearby attractions: History of Diving Museum - 3 km, Rain Barrel Village - 5.3 km

Sands of Islamorada

  • Why it's great: At Sands of Islamorada, travelers can enjoy a delightful outdoor pool that is perfect for soaking up the sun. This budget-friendly hotel, with a review rating of 9 out of 10, has a welcoming atmosphere for those looking to relax by the water.
  • Other amenities: Along with the refreshing pool, the hotel provides free toiletries and Wi-Fi for added convenience. Guests can also benefit from kitchenettes in their rooms, beach towels, and self-parking. Located near the sea, the hotel features a lovely garden, ensuring a peaceful stay amidst nature.
  • Neighborhood: Matecumbe
  • Nearby attractions: Indian Key Historic State Park - 1 km, Florida Keys Brewing Co. - 2.7 km

Drop Anchor

  • Why it's great: Drop Anchor is an ideal choice for pool enthusiasts, featuring a stunning outdoor pool and sun loungers that invite relaxation. With a solid review rating of 9 out of 10 and a comfortable 3-star rating, travelers can enjoy a rejuvenating stay that focuses on leisure and comfort.
  • Other amenities: The hotel also offers convenient amenities such as complimentary toiletries and free Wi-Fi. Guests can take advantage of nearby ocean activities, including sailing and kayaking, as well as a walkway to the water. With a kitchen in each room, beach towels provided, and daily housekeeping, travellers will find everything they need for a comfortable stay.
  • Nearby attractions: Windley Key Fossil Reef Geological State Park - 0.7 km, Rain Barrel Village - 4 km, Islamorada County Park - 4.3 km

Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"Quiet and beautiful"
Mark 4-night trip
Posted 2 hours ago
Islander Resort

Frequently asked questions

What are the best hotels in Islamorada with outdoor pools?
The Caribbean Resort in Islamorada is a charming 3.5-star hotel that boasts an impressive outdoor pool, great for families seeking relaxation and fun. Guests rave about the beautiful and clean rooms, as well as the helpful staff who go above and beyond to ensure a great stay. With ocean views and easy access to nearby beaches, this resort offers a delightful blend of comfort and convenience.

Another fantastic option is the Sunset Inn, a cozy 3-star hotel known for its warm outdoor pool and spacious rooms. Travellers appreciate the friendly and helpful staff, as well as the central location that makes exploring Islamorada a breeze. With free bicycle rentals and self-parking, it's an excellent value for families wanting to make the most of their adventure.

For a more upscale experience, consider Casa Morada, also a 3.5-star hotel, which features an inviting outdoor pool alongside a poolside bar. Guests enjoy complimentary breakfast and praise the excellent reception and helpful staff. The comfortable rooms and good facilities make it a popular choice among travellers who value quality.

Chesapeake Beach Resort, another 3.5-star gem, offers a clean and well-maintained outdoor pool, along with friendly service and a beautiful location. Guests love the complimentary breakfast and the comfortable, clean rooms that enhance their stay in this picturesque destination.

Lastly, for those looking for a luxurious escape, Cheeca Lodge & Spa stands out with its stunning outdoor pool and resort-style amenities. This 5-star hotel features a poolside bar, cabanas, and even private beach access, ensuring a lavish experience. Guests frequently highlight the exceptional service, beautiful accommodations, and delicious food, making it a top choice for those wishing to indulge during their family getaway.
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 CA $132 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 retreat in Islamorada that offers an exceptional experience for travellers seeking luxury and privacy. With its private outdoor pools, guests can enjoy a serene atmosphere, lounging in poolside cabanas or taking a refreshing dip while savoring the beautiful surroundings.

This resort is highly rated, boasting a traveller review score of 9.2, and it's no surprise why. Guests rave about the friendly and amazing staff, the beautiful and clean rooms, and the overall excellent service. The amenities are designed for relaxation and indulgence, featuring options like a private hot tub, deep-soaking bathtubs, and even massages on the beach for those looking to unwind.

In addition to the luxurious pools, Cheeca Lodge & Spa provides a range of activities, including onsite tennis and golf, ensuring that families and couples alike can find something to enjoy. The beachfront restaurant offers delicious dining options, superb for a sunset meal after a day filled with adventure.
What are some of the best Islamorada hotels with outdoor pools and scenic views?
The Caribbean Resort is a delightful 3.5-star hotel that offers an unforgettable stay with its outdoor pool and breathtaking ocean views. Guests have praised the staff for being incredibly helpful, while the rooms are noted for their beautiful and clean designs. The resort features convenient amenities like pool sun loungers and easy access for those with mobility needs, making it a wonderful option for families seeking both relaxation and adventure.

For those looking for a mix of comfort and great service, the Chesapeake Beach Resort, also rated at 3.5 stars, is another excellent choice. Its outdoor pool is well-maintained, and the complimentary continental breakfast is a hit among travellers, who describe the staff as friendly and the location as beautifully scenic. The resort boasts lovely beach views, creating an inclusive setting for families wanting to soak up the sun.

If luxury is on your agenda, Cheeca Lodge & Spa stands out as a 5-star gem. It features a stunning outdoor pool surrounded by cabanas, a poolside bar, and a private beach area, making it great for those who enjoy upscale relaxation. Guests rave about the friendly and amazing staff, coupled with the beautifully clean rooms and excellent dining options, ensuring a memorable experience for everyone.

For a more laid-back vibe, the Islander Resort, rated 4 stars, provides an inviting outdoor pool, poolside bar, and stunning beach views. Families will appreciate the spacious rooms and the attentive service, which travellers have highlighted as both friendly and accommodating.

Lastly, the Pines & Palms Resort offers a cozy atmosphere with its outdoor pool and beautiful ocean views, great for families looking to enjoy a peaceful retreat. With clean rooms and a welcoming location, it's an ideal spot to unwind after a day of adventure in the scenic surroundings of Islamorada.
Are there hotels in Islamorada with outdoor pool cabanas or loungers?
The Cheeca Lodge & Spa is a luxurious 5-star retreat in Islamorada that offers an exquisite experience with its outdoor pool, complete with inviting cabanas and sun loungers. Guests rave about the stunning amenities and exceptional service, making it a top choice for those seeking relaxation and adventure alike.

Another excellent option is the Islander Resort, rated 9.2 by travellers. This 4-star hotel features spacious outdoor pool cabanas and sun loungers, great for families looking to unwind after a day of exploring. The pool area is described as beautiful and expansive, providing a serene atmosphere for both adults and children.

For those seeking a charming stay, the Sunset Inn offers a cozy 3-star experience. With free pool cabanas and a warm, welcoming pool environment, this hotel boasts a stellar review rating of 9.4, where guests appreciate the cleanliness and helpful staff.

Lastly, Casa Morada, a 3.5-star hotel, offers resort-inclusive amenities including outdoor pool sun loungers and a poolside bar, ensuring a delightful day in the sun. With a rating of 9.4, guests praise the comfort of the rooms and the excellent reception service.
Which Islamorada hotels offer poolside service for food and drinks?
Casa Morada is a charming 3.5-star hotel that offers an inviting outdoor pool experience alongside a delightful poolside bar. Guests have praised the hotel for its comfortable and excellent rooms, along with the helpful staff that make your stay even more enjoyable. With a traveller review score of 9.4, it's clear that visitors appreciate the quality of service and amenities available.

Another top choice is the luxurious Cheeca Lodge & Spa, a 5-star gem that features an expansive outdoor pool, complete with poolside cabanas and a bar serving refreshing drinks. Guests rave about the beautiful and clean rooms, as well as the amazing service provided by the friendly staff. With a stellar review score of 9.2, this hotel not only caters to your relaxation needs but also offers a range of amenities, including a beachfront restaurant and spa services.

For a well-rounded stay, the Islander Resort stands out with its outdoor pool and poolside bar, superb for cooling off and enjoying a drink in the sun. Rated at 9.2, guests love the beautiful and spacious pool area, along with the friendly staff that enhance the overall experience.

If you're looking for a more intimate setting, consider the Pines & Palms Resort, a 3-star option that also provides an inviting outdoor pool with a poolside bar. With a review score of 9.2, it's noted for its beautiful location and clean rooms, making it a cozy retreat for families and couples alike.

Lastly, Amara Cay Resort, a 4-star hotel, features a lovely outdoor pool with poolside service for food and drinks. Guests have appreciated the beautiful location and comfortable accommodations, giving it a rating of 8.8. The friendly staff and the beachside restaurant add to the hotel's appeal, ensuring a delightful experience during your stay in Islamorada.
Are there hotels with outdoor pools that are close to MoradaWay Arts & Cultural District?
The Caribbean Resort in Islamorada offers a delightful experience for travellers, featuring a stunning outdoor pool that promises relaxation and enjoyment. With a great review score of 10.0, guests rave about the helpful staff and beautiful, clean rooms, making it an ideal choice for those seeking quality and convenience.

Just a short distance from the MoradaWay Arts & Cultural District, the Sunset Inn is another fantastic option. This 3-star hotel boasts a warm outdoor pool and spacious, clean rooms. Rated at 9.4, travellers appreciate the friendly service and excellent central location, along with free bicycle rentals that make exploring the area even easier.

For a more upscale experience, Casa Morada, also rated 9.4, provides a resort-style outdoor pool complemented by a poolside bar and free breakfast options. Guests love the comfortable accommodations and attentive staff, making it a great spot for families looking to unwind after a day of adventure.

Finally, if you're in search of a luxurious retreat, Cheeca Lodge & Spa stands out with its expansive outdoor pool, poolside cabanas, and a host of amenities including a beachfront restaurant and a wellness spa. With a rating of 9.2, it's renowned for its exceptional service and beautiful surroundings, creating a memorable getaway for those who wish to indulge.
Are there hotels in Islamorada with outdoor pool activities or events?
Islamorada, Florida, is a tropical paradise famed for its stunning beaches and crystal-clear waters, making it a fantastic destination for those seeking relaxation and adventure alike. Notably, several hotels in this charming area offer inviting outdoor pools that enhance the guest experience with a blend of leisure and excitement.

For families looking for a fun-filled getaway, the Cheeca Lodge & Spa stands out with its luxurious family pool area, complemented by a full-service watersports facility nearby. This allows for a mix of poolside relaxation and thrilling aquatic adventures, ensuring there's something for everyone. The option to reserve private cabanas by the spa pool or infinity pool adds an extra touch of luxury, superb for parents wanting a serene escape while kids enjoy the water.

Couples seeking a romantic retreat will love the Chesapeake Beach Resort, which features two outdoor pools with breathtaking ocean views. The resort's oceanfront event venue creates opportunities for intimate gatherings or sunset celebrations, providing a picturesque backdrop for unforgettable moments together.

For those who appreciate a more laid-back atmosphere, the Fisher Inn Resort & Marina offers an outdoor heated pool surrounded by sun loungers and outdoor furniture. This setting is ideal for leisurely days spent soaking up the sun, with easy access to the beach for a refreshing dip in the ocean.

With a variety of hotels that blend outdoor pool activities with great experiences, Islamorada promises a delightful stay for all types of travellers.
Is it cheaper to book flights and a hotel in Islamorada 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 travel 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 with an outdoor pool in Islamorada for you.
How can I save on a hotel in Islamorada with Expedia?
Before booking your Islamorada hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access instant discounts with Member Prices as well as member-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

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