Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

This weekend
Jun 26 - Jun 28
Next weekend
Jul 3 - Jul 5

Our top choices for Islamorada hotels with a pool

View from property

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,336 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is ￥20,871
￥30,750 total
includes taxes & fees
Jun 28 - Jun 29
Lime Tree Bay Resort
Property grounds

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,328 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is ￥37,099
￥53,551 total
includes taxes & fees
Jul 19 - Jul 20
Cheeca Lodge & Spa
Exterior detail

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 ￥23,579
￥26,526 total
includes taxes & fees
Jun 30 - Jul 1
Rock Reef Resort
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,742 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is ￥29,865
￥42,685 total
includes taxes & fees
Jul 5 - Jul 6
Chesapeake Beach Resort
Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (158 reviews)
The price is ￥20,550
￥45,839 total
includes taxes & fees
Jun 24 - Jun 25
Treasure Harbor
Outdoor pool, pool umbrellas, sun loungers

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 ￥24,985
￥34,460 total
includes taxes & fees
Jun 28 - Jun 29
Coconut Palm Inn
View from property

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,758 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkeling, and sunset watching create unforgettable aquatic moments.
The price is ￥19,246
￥25,691 total
includes taxes & fees
Jul 19 - Jul 20
Bayside Inn Key Largo
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (700 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is ￥18,327
￥28,980 total
includes taxes & fees
Jul 1 - Jul 2
Breezy Palms Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
The price is ￥22,686
￥31,167 total
includes taxes & fees
Jul 22 - Jul 23
Drop Anchor
Private beach, white sand, sun loungers, beach towels

Bay Harbor Lodge

Bay Harbor Lodge
3.0 star property
Rock Harbor
9.4 out of 10, Exceptional, (695 reviews)
  • cleanliness
    Soak in serenity at this pristine waterfront lodge with a quiet pool and private beach access.
The price is ￥33,067
￥37,201 total
includes taxes & fees
Jun 29 - Jun 30
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.
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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, (1742)
The price is ￥29,865
￥42,685 total
includes taxes & fees
Jul 5 - Jul 6
Chesapeake Beach Resort
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Hotels with pools and hot tubs in Islamorada

Breadfruit Suite | Terrace/patio
Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor
9.8 out of 10, Exceptional, (328)
The price is ￥30,389
￥38,733 total
includes taxes & fees
Jun 24 - Jun 25
Kona Kai Resort and Gallery - Adults Only
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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, (1292)
The price is ￥27,687
￥42,964 total
includes taxes & fees
Jul 19 - Jul 20
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

10/10 Excellent
"Love the pier where our kids can fish."
Amy 8-night trip
Posted 9 hours ago
Cheeca Lodge & Spa

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.