Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

Tonight
Feb 28 - Mar 1
Tomorrow
Mar 1 - Mar 2
Next weekend
Mar 6 - Mar 8
In two weeks
Mar 13 - Mar 15

Our top choices for Islamorada hotels with a pool

Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (136 reviews)
The price is ₩269,387
₩504,456 total
includes taxes & fees
Mar 1 - Mar 2
Treasure Harbor
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, (1,174 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
Lime Tree Bay Resort
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (624 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is ₩248,251
₩353,916 total
includes taxes & fees
Mar 25 - Mar 26
Breezy Palms Resort
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,097 reviews)
  • cleanliness
    Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views.
Rock Reef 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, (1,001 reviews)
  • cleanliness
    Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
The price is ₩303,114
₩391,128 total
includes taxes & fees
Mar 1 - Mar 2
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, (669 reviews)
  • cleanliness
    Soak in serenity at this pristine waterfront lodge with a quiet pool and private beach access.
The price is ₩379,520
₩426,967 total
includes taxes & fees
Mar 3 - Mar 4
Bay Harbor Lodge
Exterior

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,679 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkeling, and sunset watching create unforgettable aquatic moments.
The price is ₩334,693
₩412,333 total
includes taxes & fees
Mar 8 - Mar 9
Bayside Inn Key Largo
Beach/ocean view

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,659 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is ₩422,703
₩556,534 total
includes taxes & fees
Mar 3 - Mar 4
Chesapeake Beach Resort
Outdoor pool, sun loungers

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
La Jolla Resort
Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,254 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is ₩443,716
₩603,914 total
includes taxes & fees
Mar 8 - Mar 9
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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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, (1659)
The price is ₩422,703
₩556,534 total
includes taxes & fees
Mar 3 - Mar 4
Chesapeake Beach Resort
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4-star hotels with pools in Islamorada

Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1254)
The price is ₩443,716
₩603,914 total
includes taxes & fees
Mar 8 - Mar 9
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.
View all properties

Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance. "
James 2-night trip
Posted 2 days 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 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.