A beach with white lounge chairs, a covered pavilion, and palm trees.

Hotels with Swimming Pool in Islamorada, Florida

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Check availability on Islamorada Hotels with Swimming Pool

This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

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, (1,355 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is P7,903
P11,644 total
includes taxes & fees
Jul 5 - Jul 6
Lime Tree Bay Resort
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (704 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is P5,899
P9,816 total
includes taxes & fees
Jul 6 - Jul 7
Breezy Palms Resort
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 P10,956
P12,326 total
includes taxes & fees
Jul 13 - Jul 14
Rock Reef Resort
Water view

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 P8,604
P11,820 total
includes taxes & fees
Jul 2 - Jul 3
Drop Anchor
Property grounds

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 P12,207
P18,219 total
includes taxes & fees
Jul 8 - Jul 9
Cheeca Lodge & Spa
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, (1,746 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is P12,146
P17,106 total
includes taxes & fees
Jul 14 - Jul 15
Chesapeake Beach Resort
Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (161 reviews)
The price is P8,271
P17,907 total
includes taxes & fees
Jul 8 - Jul 9
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 P11,238
P15,058 total
includes taxes & fees
Jul 5 - Jul 6
Coconut Palm Inn
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, (329 reviews)
  • cleanliness
    Oceanfront pool sanctuary with sunset views makes this adults-only haven a serene Florida Keys retreat.
The price is P17,108
P20,967 total
includes taxes & fees
Jul 2 - Jul 3
Kona Kai Resort and Gallery - Adults Only
Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,290 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is P11,521
P17,435 total
includes taxes & fees
Jul 12 - Jul 13
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, (1746)
The price is P12,146
P17,106 total
includes taxes & fees
Jul 14 - Jul 15
Chesapeake Beach Resort
View all properties

Hotels with pools and hot tubs in Islamorada

Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1331)
The price is P12,207
P18,219 total
includes taxes & fees
Jul 8 - Jul 9
Cheeca Lodge & Spa
View all properties

4-star hotels with pools in Islamorada

Exterior
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1002)
The price is P18,536
P24,226 total
includes taxes & fees
Jul 22 - Jul 23
Playa Largo Resort & Spa, Autograph Collection
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
"Very nicely put together and well maintained. Staff are great and the views are stunning. We will go back again."
Tony 2-night trip
Posted 13 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 150 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 150 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.

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