Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a 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, (1,235 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is NT$5,539
NT$7,663 total
includes taxes & fees
Apr 28 - Apr 29
Lime Tree Bay Resort
Beach/ocean view

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,701 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is NT$6,618
NT$9,235 total
includes taxes & fees
May 7 - May 8
Chesapeake Beach Resort
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,127 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 NT$6,270
NT$7,054 total
includes taxes & fees
Apr 28 - Apr 29
Rock Reef Resort
Exterior

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1,010 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is NT$4,838
NT$6,481 total
includes taxes & fees
May 6 - May 7
Fisher Inn Resort & Marina
Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (148 reviews)
The price is NT$4,552
NT$9,595 total
includes taxes & fees
Apr 21 - Apr 22
Treasure Harbor
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 NT$8,627
NT$12,032 total
includes taxes & fees
Apr 29 - Apr 30
Cheeca Lodge & Spa
Exterior

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,712 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkeling, and sunset watching create unforgettable aquatic moments.
The price is NT$4,896
NT$6,303 total
includes taxes & fees
May 10 - May 11
Bayside Inn Key Largo
Exterior

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (242 reviews)
  • cleanliness
    Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
The price is NT$7,054
NT$7,936 total
includes taxes & fees
Apr 14 - Apr 15
Ragged Edge Resort & Marina
Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,276 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is NT$9,641
NT$13,173 total
includes taxes & fees
Apr 27 - Apr 28
Amara Cay Resort
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (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 NT$10,689
NT$14,172 total
includes taxes & fees
May 10 - May 11
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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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, (1701)
The price is NT$6,618
NT$9,235 total
includes taxes & fees
May 7 - May 8
Chesapeake Beach Resort
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Hotels with pools and hot tubs in Islamorada

Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1316)
The price is NT$8,627
NT$12,032 total
includes taxes & fees
Apr 29 - Apr 30
Cheeca Lodge & Spa
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4-star hotels with pools in Islamorada

Property grounds
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1034)
The price is NT$11,200
NT$14,354 total
includes taxes & fees
May 13 - May 14
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Breakfast was great, views were awesome, nice little private beach (rare in the keys) perfect location with plenty of night life walking distance and near by! Would stay again for sure!"
Kenneth 3-night trip
Posted 1 hour ago
Chesapeake Beach Resort

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 152 places to stay with pools. During your trip, you can explore sights such as Everglades National Park and Bud n' Mary's Dive Center, 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 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 should I expect 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 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.

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