Hotels with Pool & Resorts in Islamorada from AU$230

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Check availability on Islamorada Hotels with Pool

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, (1,310 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is AU$270
includes taxes & fees
17 June - 18 June
Lime Tree Bay Resort
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,747 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is AU$376
includes taxes & fees
14 June - 15 June
Chesapeake Beach Resort
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,148 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 AU$273
includes taxes & fees
24 June - 25 June
Rock Reef Resort
Exterior

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,007 reviews)
  • cleanliness
    Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
The price is AU$230
includes taxes & fees
14 June - 15 June
Drop Anchor
Property grounds

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,322 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is AU$537
includes taxes & fees
28 June - 29 June
Cheeca Lodge & Spa
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (694 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is AU$267
includes taxes & fees
1 July - 2 July
Breezy Palms Resort
Outdoor pool, pool umbrellas, pool loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,300 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is AU$395
includes taxes & fees
23 June - 24 June
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, (325 reviews)
  • cleanliness
    Oceanfront pool sanctuary with sunset views makes this adults-only haven a serene Florida Keys retreat.
The price is AU$313
includes taxes & fees
11 June - 12 June
Kona Kai Resort and Gallery - Adults Only
Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (158 reviews)
The price is AU$404
includes taxes & fees
21 June - 22 June
Treasure Harbor
View from property

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,762 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkelling, and sunset watching create unforgettable aquatic moments.
The price is AU$249
includes taxes & fees
14 June - 15 June
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
Spa pool

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, (1747)
The price is AU$376
includes taxes & fees
14 June - 15 June
Chesapeake Beach Resort
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Hotels with pools and spa pools in Islamorada

Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1322)
The price is AU$537
includes taxes & fees
28 June - 29 June
Cheeca Lodge & Spa
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4-star hotels with pools in Islamorada

Room, 1 King Bed with Sofa bed, Oceanfront (Alligator Reef, Lanai) | View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1300)
The price is AU$395
includes taxes & fees
23 June - 24 June
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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Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"This resort was absolutely amazing and exceeded all of my expectations. We originally booked just one night on our way to Key West, but after experiencing everything the property had to offer, we wished we had stayed much longer. If we have the opportunity to make this trip again, we would choose to stay here for our entire vacation and simply take a day trip or two to Key West. The resort offers everything you need for a relaxing and enjoyable stay, with beautiful surroundings, excellent amenities, and a welcoming atmosphere. Our only regret is that we didn't spend more time here. This was one of the highlights of our trip, and we would not hesitate to return or recommend it to others looking for the perfect Florida Keys getaway. The extra special touch was the gift for our anniversary. Breakfast."
Amanda 1-night trip
Posted 4 hours ago
Islander Resort

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 146 places to stay with pools. During your visit, you can explore sights such as Everglades National Park and Founders Park, 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. 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 will I be able to find in Islamorada?
Expedia's 146 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.