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

Islamorada Hotel Guide - Hotels with Pool in Islamorada, Florida

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Check availability on Islamorada Hotels with Pool

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Islamorada hotels with a pool

Poolside bar

Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
Key Largo
9.4 out of 10, Exceptional, (1,480 reviews)
  • cleanliness
    Dive into coastal bliss with a splashy pool scene and beachfront perks for aquatic adventures.
The price is €241
includes taxes & fees
26 Jul - 27 Jul
Reefhouse Resort & Marina
Suite, Multiple Beds, Bay View

Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys
3.0 star property
Marathon
9.2 out of 10, Wonderful, (1,176 reviews)
  • cleanliness
    Float away in a paradise with two outdoor pools, poolside dining, and marina views.
The price is €156
includes taxes & fees
12 Jul - 13 Jul
Fairfield Inn & Suites by Marriott Marathon Florida Keys
View from property

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,366 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is €158
includes taxes & fees
8 Jul - 9 Jul
Lime Tree Bay Resort
Outdoor pool, open 8 AM to 10 PM, pool loungers

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1,014 reviews)
  • cleanliness
    Pool paradise awaits with breathtaking bay views and a pristine private beach just steps away.
The price is €133
includes taxes & fees
19 Jul - 20 Jul
Hampton Inn Key Largo Manatee Bay
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,737 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is €216
includes taxes & fees
3 Aug - 4 Aug
Chesapeake Beach Resort
Outdoor pool, pool cabanas (surcharge), pool umbrellas

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Vibrant poolside retreat beckons with 24-hour access and luxurious cabanas for ultimate relaxation.
The price is €346
includes taxes & fees
19 Jul - 20 Jul
Playa Largo Resort & Spa, Autograph Collection
Property grounds

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,332 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is €260
includes taxes & fees
16 Jul - 17 Jul
Cheeca Lodge & Spa
Outdoor pool, pool umbrellas, pool loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,287 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is €229
includes taxes & fees
19 Jul - 20 Jul
Amara Cay Resort
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,157 reviews)
  • cleanliness
    Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views.
The price is €176
includes taxes & fees
9 Jul - 10 Jul
Rock Reef Resort
2 outdoor pools, pool umbrellas, pool loungers

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1,128 reviews)
  • cleanliness
    Escape to a beachside oasis with two outdoor pools, a hot tub, and poolside dining and cocktails.
The price is €345
includes taxes & fees
3 Aug - 4 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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
Hot tub

Hotels with pools and free breakfast in Islamorada

Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1737)
The price is €216
includes taxes & fees
3 Aug - 4 Aug
Chesapeake Beach Resort
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Hotels with pools and hot tubs in Islamorada

Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1332)
The price is €260
includes taxes & fees
16 Jul - 17 Jul
Cheeca Lodge & Spa
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4-star hotels with pools in Islamorada

Room, 1 King Bed with Sofa bed, Oceanfront (Alligator Reef, Lanai) | View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1287)
The price is €229
includes taxes & fees
19 Jul - 20 Jul
Amara Cay 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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Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

8/10 Good
"I recently stayed at Cheeca Lodge in Suite 730. Overall, I enjoyed my stay and would return, but there were a few things worth noting. The suite was spacious, comfortable, and well designed. The only cleanliness issue I noticed was a few hairs left in the bathtub. There were several maintenance issues. The elevator was extremely hot and made concerning noises, the ice machine at the bottom of our building was out of service, and the ice maker in the suite’s kitchen freezer didn’t work, so we had to go to another building for ice. The resort grounds are beautiful, but the two main pools were packed during our stay. The beach was also covered in seaweed, and the smell made it less enjoyable. We spent most of our time at the adult pool, which was much more relaxing, though seating is limited and many chairs are reserved for cabanas, so get there early. Food and drinks were a highlight. The adult pool bar serves food, and the turkey club sandwich was excellent. The main bar had a great atmosphere and stayed open late, which we appreciated. The par-3 golf course was a fun bonus, and free club rentals are included in the daily resort fee. Just don’t expect a traditional golf experience. The greens are not greens lol. One of the best parts of the resort is its location. It’s close to everything, and the complimentary shuttle within a 2-mile radius is a great perk. Despite a few maintenance issues and crowded amenities, we had a great stay overall and would definitely return."
Kyle 3-night trip
Posted 8 hours ago
Cheeca Lodge & Spa

Frequently asked questions

What's it like visiting Islamorada?
If spending time by the pool is your idea of the perfect getaway, you might want to think about relaxing Islamorada, which offers 150 places to stay with pools. During your visit, you can explore sights such as Everglades National Park and Bud n' Mary's Dive Center, and then take it easy poolside at one of the accommodation options in Islamorada that guests like for their pools.
What are some accommodation options with pools in Islamorada?
Chesapeake Beach Resort: Features a private beach, 2 outdoor swimming pools and daily. Fisher Inn Resort & Marina: Offers a private beach, a pool and daily. Bayside Villas by Islander Resort: Provides 3 restaurants, an outdoor pool and free self parking. Drop Anchor: Features free self parking, an outdoor pool and complimentary bicycles.
How many pool hotels will I be able to find in Islamorada?
Expedia's 150 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Explore places such as Everglades National Park while you're in Islamorada. Enjoy a stroll along the shore at Anne's Beach and Sunset Drive Beach. Islamorada appeals to visitors with its beautiful ocean views and top seafood restaurants.
When is the best time to book a hotel with a pool in Islamorada?
Taking the local weather in Islamorada into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.