Find Hotels with a Pool in Islamorada, FL

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Islamorada Hotels with a Pool

This weekend
Next weekend

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, (1,338 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is AED 445
AED 666 total
includes taxes & fees
1 Jul - 2 Jul
Lime Tree Bay Resort

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,331 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is AED 843
AED 1,217 total
includes taxes & fees
20 Jul - 21 Jul
Cheeca Lodge & Spa

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,158 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 AED 536
AED 603 total
includes taxes & fees
25 Jun - 26 Jun
Rock Reef Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,744 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is AED 679
AED 970 total
includes taxes & fees
2 Jul - 3 Jul
Chesapeake Beach Resort

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (159 reviews)
The price is AED 467
AED 1,042 total
includes taxes & fees
28 Jun - 29 Jun
Treasure Harbor

Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (545 reviews)
  • cleanliness
    Waterside bliss with a private beach and pristine pool creates an island sanctuary at this Florida Keys retreat.
The price is AED 575
AED 792 total
includes taxes & fees
28 Jun - 29 Jun
Coconut Palm Inn

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,753 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkeling, and sunset watching create unforgettable aquatic moments.
The price is AED 424
AED 568 total
includes taxes & fees
25 Jun - 26 Jun
Bayside Inn Key Largo

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (701 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is AED 386
AED 624 total
includes taxes & fees
6 Jul - 7 Jul
Breezy Palms Resort

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
The price is AED 517
AED 710 total
includes taxes & fees
12 Jul - 13 Jul
Drop Anchor

Bay Harbor Lodge

Bay Harbor Lodge
3.0 star property
Rock Harbor
9.4 out of 10, Exceptional, (696 reviews)
  • cleanliness
    Soak in serenity at this pristine waterfront lodge with a quiet pool and private beach access.
The price is AED 753
AED 847 total
includes taxes & fees
29 Jun - 30 Jun
Bay Harbor Lodge
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

Explore a world of travel with Expedia

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 154 places to stay with pools. During your trip, you can explore sights such as Everglades National Park and Bud n' Mary's Dive Center, 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 154 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Explore places like 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 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.