Islamorada Hotels with Swimming Pool

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Check availability on Islamorada Hotels with Swimming Pools

Our top choices for Islamorada hotels with a pool

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,695 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is RM786
RM1,107 total
includes taxes & fees
10 May - 11 May
Chesapeake Beach Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,240 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is RM688
RM952 total
includes taxes & fees
19 Apr - 20 Apr
Lime Tree Bay Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,131 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 RM779
RM876 total
includes taxes & fees
28 Apr - 29 Apr
Rock Reef Resort

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,319 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is RM1,183
RM1,621 total
includes taxes & fees
3 May - 4 May
Cheeca Lodge & Spa

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (149 reviews)
The price is RM566
RM1,194 total
includes taxes & fees
21 Apr - 22 Apr
Treasure Harbor

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,710 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkelling, and sunset watching create unforgettable aquatic moments.
The price is RM609
RM784 total
includes taxes & fees
10 May - 11 May
Bayside Inn Key Largo

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,003 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is RM568
RM768 total
includes taxes & fees
6 May - 7 May
Fisher Inn Resort & Marina

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (658 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is RM529
RM800 total
includes taxes & fees
26 Apr - 27 Apr
Breezy Palms Resort

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1,022 reviews)
  • cleanliness
    Tranquil poolside paradise in Key Largo where warm waters meet a private beachfront setting and stunning ocean vistas await.
The price is RM658
RM811 total
includes taxes & fees
13 May - 14 May
Ocean Pointe Suites at Key Largo

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,278 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is RM1,199
RM1,639 total
includes taxes & fees
30 Apr - 1 May
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.

Choose what matters most at hotels with a pool in Islamorada

Hotels with pools and free breakfast in Islamorada

Hotels with pools and hot tubs in Islamorada

4-star hotels with pools in Islamorada

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.

Top Islamorada Hotel Reviews

Frequently asked questions

What's it like visiting Islamorada?
If spending time 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 visit, you can explore sights such as Everglades National Park and Bud n' Mary's Dive Center, and then take it easy poolside at one of the accommodation options in Islamorada that guests like for their pools.
What are some accommodation options with pools in Islamorada?
Chesapeake Beach Resort: Features a private beach, 2 outdoor swimming 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 will I be able 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 such as 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 the local weather in Islamorada into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.

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