Find Hotels with a Pool in Islamorada, FL

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Pick from 31 Islamorada Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Amara Cay Resort
Outdoor pool, pool umbrellas, sun loungers
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1211)
"My family truly enjoyed this resort. Extremely satisfied. We are your customers from now on. Thank you. "
The price is NT$5,410
NT$8,247 total
includes taxes & fees
Dec 3 - Dec 4
Amara Cay Resort
Islander Resort
2 outdoor pools, cabanas (surcharge), pool umbrellas
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1003)
"They had much construction going on When finished should be excellent place to stay"
The price is NT$7,253
NT$9,951 total
includes taxes & fees
Dec 1 - Dec 2
Islander Resort
La Siesta Resort & Villas
Outdoor pool, sun loungers
La Siesta Resort & Villas
4.0 star property
8.6 out of 10, Excellent, (1001)
"Very roomy Great access to wonderful water activities Clean and beautiful Lots of parking Friendly staff Beds and pillows could be more comfortable. "
The price is NT$9,733
NT$13,110 total
includes taxes & fees
Nov 30 - Dec 1
La Siesta Resort & Villas
Cheeca Lodge & Spa
Property grounds
Cheeca Lodge & Spa
5.0 star property
9.0 out of 10, Wonderful, (1007)
"Property was lovely. Staff was amazing. Breathtaking views, great restaurants and awesome tiki bar. Highly recommended."
The price is NT$9,683
NT$13,086 total
includes taxes & fees
Nov 24 - Nov 25
Cheeca Lodge & Spa
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor
3.0 star property
8.8 out of 10, Excellent, (1000)
"Nice cute quiet place. "
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Outdoor pool, a heated pool, pool umbrellas, sun loungers
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3.0 star property
8.0 out of 10, Very Good, (1004)
"The hotel and stAffwereamazing. Two of restaurants were being redone so our dinner choices on site were limited. Setting that aside, this place is unbelievably good for the price. A marina with boardwalk, live entertainment, a real Tiki bar, two perfect beach areas and great salt water swimming pools. Even an ice cream shop and a beachwear store on site."
The price is NT$10,366
NT$13,819 total
includes taxes & fees
Nov 26 - Nov 27
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort
Outdoor pool, a heated pool, pool umbrellas, sun loungers
Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (974)
"Place was under heavy construction, when booking stay know one mentioned the whole resort is under reconstruction. Besides the construction the location was beautiful setting "
Pines & Palms Resort
Fisher Inn Resort & Marina
Outdoor pool, a heated pool, open 7:00 AM to 7:00 PM, pool umbrellas
Fisher Inn Resort & Marina
3.5 star property
7.6 out of 10, Good, (1002)
"Good, clean"
The price is NT$4,527
NT$6,153 total
includes taxes & fees
Dec 3 - Dec 4
Fisher Inn Resort & Marina
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers
Islander Bayside Villas and Boatslips
3.5 star property
8.8 out of 10, Excellent, (354)
"Amazing location and place"
The price is NT$7,773
NT$10,536 total
includes taxes & fees
Dec 1 - Dec 2
Islander Bayside Villas and Boatslips
Coconut Cove Resort and Marina
Outdoor pool, sun loungers
Coconut Cove Resort and Marina
2.5 star property
7.4 out of 10, Good, (682)
"Great spot. Beautiful views. Great pool. Staff friendly "
The price is NT$7,441
NT$8,372 total
includes taxes & fees
Nov 23 - Nov 24
Coconut Cove Resort and Marina
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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Frequently asked questions

What's it like visiting Islamorada?
If taking it easy by the pool is your idea of the perfect getaway, you might want to think about relaxing Islamorada, which offers 21 places to stay with pools. During your trip, you can explore sights such as Everglades National Park and Florida Keys Brewing Co., and then relax and unwind poolside at one of the accommodations in Islamorada that guests like for their pools.
What are some accommodations with pools in Islamorada?
Chesapeake Beach Resort: Features a private beach, 2 outdoor pools, and sun loungers. Drop Anchor: Offers free self parking, an outdoor pool, and complimentary bicycles. Fisher Inn Resort & Marina: Provides a private beach, a pool, and daily. Sands of Islamorada: Features free self parking, a pool, and complimentary wireless internet access. Islander Bayside Villas and Boatslips: Offers free self parking, an outdoor pool, and complimentary wireless internet access.
How many pool hotels should I expect to find in Islamorada?
Expedia’s 21 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Explore places like 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 into account the local weather in Islamorada is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.