Hotels with Pool & Resorts in Islamorada from NZ$246

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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, (1,307 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is NZ$328
includes taxes & fees
14 June - 15 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, (1,746 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is NZ$466
includes taxes & fees
22 June - 23 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 NZ$312
includes taxes & fees
16 June - 17 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 NZ$298
includes taxes & fees
10 June - 11 June
Drop Anchor
Property grounds

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,321 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is NZ$651
includes taxes & fees
22 June - 23 June
Cheeca Lodge & Spa
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (692 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is NZ$231
includes taxes & fees
14 June - 15 June
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, (1,298 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is NZ$482
includes taxes & fees
30 June - 1 July
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 NZ$378
includes taxes & fees
10 June - 11 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, (157 reviews)
The price is NZ$474
includes taxes & fees
10 June - 11 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, (1,758 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkelling, and sunset watching create unforgettable aquatic moments.
The price is NZ$302
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, (1746)
The price is NZ$466
includes taxes & fees
22 June - 23 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, (1321)
The price is NZ$651
includes taxes & fees
22 June - 23 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, (1298)
The price is NZ$482
includes taxes & fees
30 June - 1 July
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

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"We had a wonderful stay! The staff were friendly and welcoming. Our room was clean, spacious, and very comfortable, with everything we needed for a relaxing visit. The hotel amenities were excellent and really added to the overall experience. We would definitely stay here again and highly recommend it to others."
Samantha 2-night trip
Posted 10 hours ago
Fisher Inn Resort & Marina

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.