Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

Tonight
25 Mar - 26 Mar
Tomorrow
26 Mar - 27 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

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, (1,208 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
Lime Tree Bay Resort
Beach/ocean view

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,675 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is AED 804
AED 1,112 total
includes taxes & fees
14 Apr - 15 Apr
Chesapeake Beach Resort
Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (146 reviews)
The price is AED 574
AED 1,162 total
includes taxes & fees
26 Mar - 27 Mar
Treasure Harbor
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,109 reviews)
  • cleanliness
    Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views.
Rock Reef Resort
Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,260 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is AED 837
AED 1,210 total
includes taxes & fees
20 Apr - 21 Apr
Amara Cay Resort
Outdoor pool, open 8:00 AM to 11:00 PM, sun 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, (1,007 reviews)
  • cleanliness
    Tranquil poolside paradise in Key Largo where warm waters meet a private beachfront setting and stunning ocean vistas await.
The price is AED 623
AED 768 total
includes taxes & fees
20 Apr - 21 Apr
Ocean Pointe Suites at Key Largo
Exterior

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (237 reviews)
  • cleanliness
    Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
Ragged Edge Resort & Marina
Property grounds

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,301 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is AED 1,290
AED 1,720 total
includes taxes & fees
13 Apr - 14 Apr
Cheeca Lodge & Spa
Exterior

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,687 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkeling, and sunset watching create unforgettable aquatic moments.
The price is AED 731
AED 914 total
includes taxes & fees
15 Apr - 16 Apr
Bayside Inn Key Largo
Outdoor pool, open 9 AM to 9 PM, sun loungers

Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (403 reviews)
  • cleanliness
    Splash into the sunrise at this oceanside retreat with a sparkling pool for your island escape.
The price is AED 753
AED 897 total
includes taxes & fees
30 Mar - 31 Mar
Sands of Islamorada
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, (1675)
The price is AED 804
AED 1,112 total
includes taxes & fees
14 Apr - 15 Apr
Chesapeake Beach Resort
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Hotels with pools and hot tubs in Islamorada

Exterior
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.6 out of 10, Good, (1000)
The price is AED 625
AED 819 total
includes taxes & fees
21 Apr - 22 Apr
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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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, (1010)
The price is AED 1,355
AED 1,727 total
includes taxes & fees
20 Apr - 21 Apr
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

Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Clean room, great location, friendly staff."
Ashley 1-night trip
Posted 4 hours ago
Hadley Resort and Marina

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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 152 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 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.