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

Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

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, (1,757 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is NT$4,898
NT$7,334 total
includes taxes & fees
Aug 16 - Aug 17
Chesapeake Beach Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (711 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is NT$2,101
NT$4,045 total
includes taxes & fees
Aug 23 - Aug 24
Breezy Palms Resort

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,346 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is NT$6,453
NT$9,631 total
includes taxes & fees
Aug 9 - Aug 10
Cheeca Lodge & Spa

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,296 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is NT$6,107
NT$9,242 total
includes taxes & fees
Jul 27 - Jul 28
Amara Cay Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,409 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is NT$3,940
NT$5,890 total
includes taxes & fees
Aug 16 - Aug 17
Lime Tree Bay Resort

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
The price is NT$4,640
NT$6,133 total
includes taxes & fees
Aug 5 - Aug 6
La Jolla Resort

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 NT$5,012
NT$8,010 total
includes taxes & fees
Aug 20 - Aug 21
La Siesta Resort & Villas

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is NT$3,831
NT$5,368 total
includes taxes & fees
Aug 9 - Aug 10
Fisher Inn Resort & Marina

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,001 reviews)
  • cleanliness
    Dive into coastal bliss with a private beach, marina, and refreshing pool for aquatic adventures.
The price is NT$3,280
NT$4,748 total
includes taxes & fees
Aug 6 - Aug 7
Hadley Resort and Marina

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,078 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is NT$8,463
NT$11,710 total
includes taxes & fees
Aug 12 - Aug 13
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.

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 taking it easy 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 trip, you can explore sights such as Islamorada Brewery & Distillery and Florida Keys Brewing Co., and then relax and unwind poolside at one of the accommodations in Islamorada that guests like for their pools.
What are some accommodations with pools in Islamorada?
Chesapeake Beach Resort: Features a private beach, 2 outdoor 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 should I expect 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?
Make a point to visit attractions like Founders Park and MoradaWay Arts & Cultural District. Discover sights such as Islamorada Brewery & Distillery, Florida Keys Brewing Co., and Bud n' Mary's Dive Center during your stay. 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 into account the local weather in Islamorada is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.

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