Islamorada Hotel with Pool

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Our top choices for Islamorada hotels with a pool

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,206 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
Lime Tree Bay Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,673 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is HK$1,677
HK$2,328 total
includes taxes & fees
14 Apr - 15 Apr
Chesapeake Beach Resort

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (146 reviews)
The price is HK$1,211
HK$2,464 total
includes taxes & fees
24 Mar - 25 Mar
Treasure Harbor

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,106 reviews)
  • cleanliness
    Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views.
Rock Reef Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,258 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is HK$1,727
HK$2,516 total
includes taxes & fees
20 Apr - 21 Apr
Amara Cay Resort

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Tranquil poolside paradise in Key Largo where warm waters meet a private beachfront setting and stunning ocean vistas await.
The price is HK$1,359
HK$1,670 total
includes taxes & fees
20 Apr - 21 Apr
Ocean Pointe Suites at Key Largo

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (234 reviews)
  • cleanliness
    Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
Ragged Edge Resort & Marina

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,299 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is HK$2,311
HK$3,173 total
includes taxes & fees
12 Apr - 13 Apr
Cheeca Lodge & Spa

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,693 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkelling, and sunset watching create unforgettable aquatic moments.
The price is HK$1,558
HK$1,949 total
includes taxes & fees
21 Apr - 22 Apr
Bayside Inn Key Largo

Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (402 reviews)
  • cleanliness
    Splash into the sunrise at this oceanside retreat with a sparkling pool for your island escape.
The price is HK$1,574
HK$1,877 total
includes taxes & fees
24 Mar - 25 Mar
Sands of Islamorada
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

4-star hotels with pools in Islamorada

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.

Top Islamorada Hotel Reviews

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 152 places to stay with pools. During your visit, you can explore sights such as Everglades National Park and Florida Keys Brewing Co., 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. Drop Anchor: Provides free self parking, an outdoor pool and complimentary bicycles. Bayside Villas by Islander Resort: Features 3 restaurants, an outdoor pool and free self parking. Sands of Islamorada: Offers free self parking, a pool and complimentary wireless Internet access.
How many pool hotels will I be able to find in Islamorada?
Expedia's 152 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.

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