Hotels with Pool & Resorts in Islamorada from NZ$287

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Check availability on Islamorada Hotels with Pool

Tonight
19 Apr - 20 Apr
Tomorrow
20 Apr - 21 Apr
Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May

Our top choices for Islamorada hotels with a pool

Beach/ocean view

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,690 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is NZ$422
includes taxes & fees
10 May - 11 May
Chesapeake Beach Resort
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, (1,237 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$386
includes taxes & fees
3 May - 4 May
Lime Tree Bay 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 NZ$394
includes taxes & fees
20 Apr - 21 Apr
Drop Anchor
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is NZ$624
includes taxes & fees
17 May - 18 May
Islander Resort
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (660 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$287
includes taxes & fees
27 Apr - 28 Apr
Breezy Palms Resort
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,118 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$332
includes taxes & fees
10 May - 11 May
Rock Reef Resort
Exterior

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,004 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is NZ$330
includes taxes & fees
6 May - 7 May
Fisher Inn Resort & Marina
Property grounds

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,316 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is NZ$576
includes taxes & fees
3 May - 4 May
Cheeca Lodge & Spa
Exterior

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,713 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkelling, and sunset watching create unforgettable aquatic moments.
The price is NZ$337
includes taxes & fees
10 May - 11 May
Bayside Inn Key Largo
Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (150 reviews)
The price is NZ$566
includes taxes & fees
25 Apr - 26 Apr
Treasure Harbor
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, (1690)
The price is NZ$422
includes taxes & fees
10 May - 11 May
Chesapeake Beach Resort
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Hotels with pools and spa 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
8.8 out of 10, Excellent, (1003)
The price is NZ$780
includes taxes & fees
4 May - 5 May
Playa Largo Resort & Spa, Autograph Collection
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4-star hotels with pools in Islamorada

Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1002)
The price is NZ$624
includes taxes & fees
17 May - 18 May
Islander 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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

4/10 Poor
"Definitely not a 4-star experience and far from worth $1,000+ per night. The room lacked basic amenities—there was no shampoo provided, and I had to use shower gel instead. The hair dryer was also broken, and despite reporting it, no replacement was offered. The beach conditions were disappointing as well, with significant seaweed both on the shore and in the water, making it far from enjoyable. Overall, this stay did not meet expectations for the price point, and I would not recommend it."
Fatema 1-night trip
Posted 8 hours ago
Cheeca Lodge & Spa

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.