A beach with white lounge chairs, a covered pavilion, and palm trees.

Hotels with Swimming Pools in Islamorada

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Check availability on Islamorada Hotels with Swimming Pools

Our top choices for Islamorada hotels with a pool

View from property

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,380 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is S$248
includes taxes & fees
15 Jul - 16 Jul
Lime Tree Bay Resort
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,752 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is S$320
includes taxes & fees
5 Aug - 6 Aug
Chesapeake Beach Resort
Property grounds

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,346 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is S$337
includes taxes & fees
9 Aug - 10 Aug
Cheeca Lodge & Spa
Outdoor pool, pool umbrellas, pool loungers

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,293 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is S$346
includes taxes & fees
23 Jul - 24 Jul
Amara Cay Resort
View from property

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,777 reviews)
  • cleanliness
    Serene bay views from the outdoor pool where kayaking, snorkelling, and sunset watching create unforgettable aquatic moments.
The price is S$200
includes taxes & fees
12 Jul - 13 Jul
Bayside Inn Key Largo
Outdoor pool, pool umbrellas, pool loungers

Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (546 reviews)
  • cleanliness
    Waterside bliss with a private beach and pristine pool creates an island sanctuary at this Florida Keys retreat.
The price is S$317
includes taxes & fees
13 Jul - 14 Jul
Coconut Palm Inn
Aerial view

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.8 out of 10, Good, (1,004 reviews)
  • cleanliness
    Dive into blissful poolside relaxation at this marina-side retreat with a heated outdoor pool and hot tub.
The price is S$210
includes taxes & fees
14 Jul - 15 Jul
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (705 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is S$211
includes taxes & fees
2 Aug - 3 Aug
Breezy Palms Resort
Outdoor pool, open 7:00 AM to 7:00 PM, pool umbrellas, pool loungers

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,004 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is S$237
includes taxes & fees
10 Aug - 11 Aug
Fisher Inn Resort & Marina
Outdoor pool, open 8:00 AM to 8:00 PM, pool loungers

Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (792 reviews)
  • cleanliness
    Sparkling pool oasis on a private beach, where crystal waters meet endless horizons.
The price is S$277
includes taxes & fees
15 Jul - 16 Jul
Atlantic Bay 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, (1752)
The price is S$320
includes taxes & fees
5 Aug - 6 Aug
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, (1346)
The price is S$337
includes taxes & fees
9 Aug - 10 Aug
Cheeca Lodge & Spa
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4-star hotels with pools in Islamorada

View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1293)
The price is S$346
includes taxes & fees
23 Jul - 24 Jul
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

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"This was a nice place to get away from the urban Key West. The staff was very friendly and solved any issues regardless of the time (noisy neighbor, needed blanket) and the shore was close by. There was staff routinely monitoring the beach and property so it was very secure. The location has easy access to restaurants and shops if you have a car. The large pool had a bar / food and the property has a nice restaurant. The breakfast is cook to order pancakes and omelets, very nice! Pros Great staff everywhere! Ocean view is a real view if you select it We had a suite with a king bed and the teen had a separate fold out couch that was comfortable Microwave and mini-fridge were convenient Bathroom was very nice had a toilet in a separated section with a door A second pool was available with shade making it cooler in the summer Parking was easy and right outside, some covered by the buildings Elevator if you have the ocean view was very convenient Fresh omelet to order with a dozen ingredients, good yogurt options with toppings that were plentiful Balcony was very nice Reasonable price Cons - not much Next to a busy road. We could not hear it from outside the room door but there are two buildings and we were at the far building, so not bad at all for us Not much available without a car I recommend not going in June as the seaweed odor is unpleasant No one went to the beach but it was fine at the pool"
matthew 2-night trip
Posted 13 hours ago
Chesapeake Beach 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 150 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 150 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.

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