Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

Tonight
May 6 - May 7
Tomorrow
May 7 - May 8
This weekend
May 8 - May 10
Next weekend
May 15 - May 17

Our top choices for Islamorada hotels with a pool

3 outdoor pools, open 7:30 AM to 6:00 PM, sun loungers

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,271 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is ￥22,939
￥32,904 total
includes taxes & fees
May 31 - Jun 1
Lime Tree Bay Resort
Private beach, beach towels, kayaking

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,127 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 ￥24,292
￥27,328 total
includes taxes & fees
May 26 - May 27
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, (1,720 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is ￥26,931
￥39,169 total
includes taxes & fees
May 28 - May 29
Chesapeake Beach Resort
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (671 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is ￥19,524
￥24,482 total
includes taxes & fees
May 26 - May 27
Breezy Palms Resort
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is ￥28,200
￥42,371 total
includes taxes & fees
May 17 - May 18
Islander Resort
Exterior

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1,004 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is ￥21,315
￥29,126 total
includes taxes & fees
Jun 3 - Jun 4
Fisher Inn Resort & Marina
Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
The price is ￥25,409
￥50,766 total
includes taxes & fees
May 11 - May 12
Treasure Harbor
Outdoor pool, free cabanas

Sunset Inn

Sunset Inn
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Sunset island escape beckons with a heated pool, free cabanas, and beachfront tranquility along the Matecumbe shores.
The price is ￥25,934
￥30,950 total
includes taxes & fees
May 10 - May 11
Sunset Inn
Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,269 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is ￥28,967
￥44,122 total
includes taxes & fees
May 27 - May 28
Amara Cay Resort
Exterior

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, (312 reviews)
  • cleanliness
    Oceanfront pool sanctuary with sunset views makes this adults-only haven a serene Florida Keys retreat.
The price is ￥32,506
￥41,006 total
includes taxes & fees
May 7 - May 8
Kona Kai Resort and Gallery - Adults Only
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, (1720)
The price is ￥26,931
￥39,169 total
includes taxes & fees
May 28 - May 29
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, (312)
The price is ￥32,506
￥41,006 total
includes taxes & fees
May 7 - May 8
Kona Kai Resort and Gallery - Adults Only
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4-star hotels with pools in Islamorada

Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1005)
The price is ￥28,200
￥42,371 total
includes taxes & fees
May 17 - May 18
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.
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Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"The property was beautiful and the room was great. We had a double queen room with partial ocean view, but we couldn't see one bit of water. The bathroom was pretty small but the shower was amazing. Unfortunately it rained quite a bit so we were in the room and found that the TV was awful. But we will definitely be staying there again!"
Michelle 1-night trip
Posted 6 hours ago
Islander Resort

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 152 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. 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 should I expect 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 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.