Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

Tonight
May 4 - May 5
Tomorrow
May 5 - May 6
This weekend
May 8 - May 10
Next weekend
May 15 - May 17

Our top choices for Islamorada hotels with a pool

Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,263 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is ￥22,835
￥32,754 total
includes taxes & fees
May 31 - Jun 1
Lime Tree Bay Resort
Beach/ocean view

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,711 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is ￥27,433
￥39,694 total
includes taxes & fees
May 12 - May 13
Chesapeake Beach Resort
Exterior detail

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 ￥20,447
￥23,002 total
includes taxes & fees
May 7 - May 8
Rock Reef Resort
Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
The price is ￥19,642
￥44,176 total
includes taxes & fees
May 7 - May 8
Treasure Harbor
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is ￥32,030
￥46,631 total
includes taxes & fees
Jun 1 - Jun 2
Islander Resort
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (669 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is ￥13,424
￥17,606 total
includes taxes & fees
May 18 - May 19
Breezy Palms Resort
Exterior

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 ￥21,220
￥28,995 total
includes taxes & fees
Jun 3 - Jun 4
Fisher Inn Resort & Marina
Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,264 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is ￥28,519
￥43,566 total
includes taxes & fees
May 21 - May 22
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 ￥26,708
￥34,464 total
includes taxes & fees
May 7 - May 8
Kona Kai Resort and Gallery - Adults Only
Exterior

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,731 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkeling, and sunset watching create unforgettable aquatic moments.
The price is ￥23,599
￥30,474 total
includes taxes & fees
Jun 3 - Jun 4
Bayside Inn Key Largo
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, (1711)
The price is ￥27,433
￥39,694 total
includes taxes & fees
May 12 - May 13
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 ￥26,708
￥34,464 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, (1002)
The price is ￥32,030
￥46,631 total
includes taxes & fees
Jun 1 - Jun 2
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

Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"Wonderful place to stay. Quiet, private, close to everything. We will stay again"
Angelina 5-night trip
Posted 5 hours ago
Pines & Palms 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.