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Our top choices for Islamorada hotels with a pool

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,284 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
"Great waterfront view rooms, great pool and beach area."
United States
Jen
The price is ฿3,955
฿5,920 total
includes taxes & fees
26 May - 27 May
Lime Tree Bay Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,726 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
"Outdoor pool was nice as was the ocean beach."
United States
Jerry
The price is ฿6,487
฿9,135 total
includes taxes & fees
26 May - 27 May
Chesapeake Beach Resort

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,312 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
"We took the bikes and went for a long ride, played tennis swam and drink by the pool."
United States
Theodora
The price is ฿6,502
฿9,703 total
includes taxes & fees
31 May - 1 Jun
Cheeca Lodge & Spa

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 pool was impeccable"
United States
Michelle
The price is ฿5,851
฿6,583 total
includes taxes & fees
4 Jun - 5 Jun
Rock Reef Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,274 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
"Absolutely loved this resort! Amazing service and Happy Hour at the Pool! Excellent Transportation options and within walking distance to some really nice restaurants. Great stay after 3 nights in Key West for our Anniversary. Hotel staff communicated with us to plan our arrival and was able to accommodate an early check in. It was a wonderful stay, just book it!"
United States
Crystal
The price is ฿7,255
฿10,552 total
includes taxes & fees
31 May - 1 Jun
Amara Cay Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (681 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
"Very relaxed property, nice warm pool, pleasant hosts, view out into the Atlantic (small marina, no beach to access), very spacious, comfortable room, screened deck overlooking the ocean, nice shower and ample parking."
United States
Steven
The price is ฿3,254
฿4,182 total
includes taxes & fees
26 May - 27 May
Breezy Palms Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,016 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
"We enjoyed the pool and played some golf and relaxed."
United States
Linda
The price is ฿7,798
฿10,978 total
includes taxes & fees
31 May - 1 Jun
Islander Resort

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 kids loved the included kayaking and the pool."
United States
Mohammed
The price is ฿6,153
฿9,311 total
includes taxes & fees
27 May - 28 May
La Siesta Resort & Villas

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.0 out of 10, Wonderful, (2 reviews)
"La propiedad me encantó se las recomiendo 100/100%"
United States
Marta
The price is ฿5,293
฿7,057 total
includes taxes & fees
26 May - 27 May
Caloosa Cove Resort by CoolVacay

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 pool was very nice"
United States
Mark
The price is ฿6,087
฿6,847 total
includes taxes & fees
25 May - 26 May
Ragged Edge Resort & 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.

Choose what matters most at hotels with a pool in Islamorada

Hotels with pools and free breakfast in Islamorada

Hotels with pools and hot tubs in Islamorada

4-star hotels with pools in 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.

Top Islamorada Hotel Reviews

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.