Islamorada Hotel Guide - Hotels with Pool in Islamorada, Florida

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Check availability on Islamorada Hotels with Pool

Our top choices for Islamorada hotels with a pool

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, (1,300 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is €156
includes taxes & fees
26 May - 27 May
Lime Tree Bay Resort
Beach/ocean view

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,724 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is €241
includes taxes & fees
9 Jun - 10 Jun
Chesapeake Beach Resort
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,135 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 €173
includes taxes & fees
27 May - 28 May
Rock Reef Resort
Outdoor pool, open 8:00 AM to 11:00 PM, pool loungers

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Tranquil poolside paradise in Key Largo where warm waters meet a private beachfront setting and stunning ocean vistas await.
The price is €162
includes taxes & fees
7 Jun - 8 Jun
Ocean Pointe Suites at Key Largo
Outdoor pool, pool umbrellas, pool loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,272 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is €278
includes taxes & fees
7 Jun - 8 Jun
Amara Cay Resort
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,014 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is €315
includes taxes & fees
14 Jun - 15 Jun
Islander Resort
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (679 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is €176
includes taxes & fees
25 May - 26 May
Breezy Palms Resort
Exterior

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is €167
includes taxes & fees
7 Jun - 8 Jun
Fisher Inn Resort & Marina
Exterior

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (250 reviews)
  • cleanliness
    Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
The price is €180
includes taxes & fees
25 May - 26 May
Ragged Edge Resort & Marina
Outdoor pool, pool loungers

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
The price is €265
includes taxes & fees
2 Jun - 3 Jun
La Siesta Resort & Villas
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, (1724)
The price is €241
includes taxes & fees
9 Jun - 10 Jun
Chesapeake Beach Resort
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Hotels with pools and hot tubs in Islamorada

Exterior
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (263)
The price is €202
includes taxes & fees
21 Jun - 22 Jun
Coconut Cove Resort and Marina
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4-star hotels with pools in Islamorada

Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1272)
The price is €278
includes taxes & fees
7 Jun - 8 Jun
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

Amara Cay Resort

Amara Cay Resort

2/10 Terrible
"Didn't like the seclusion cleanliness set up"
Danette 4-night trip
Posted 12 hours ago
Amara Cay 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 149 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. 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 149 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.