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

Search Hotels with Swimming Pool in Islamorada

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Islamorada Hotels with Swimming Pool

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Islamorada hotels with a pool

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, (1,744 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is ₹14,447
₹21,633 total
includes taxes & fees
3 Aug - 4 Aug
Chesapeake Beach Resort
Property grounds

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,364 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is ₹14,063
₹22,815 total
includes taxes & fees
12 Aug - 13 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, (1,313 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is ₹14,950
₹23,814 total
includes taxes & fees
19 Aug - 20 Aug
Amara Cay Resort
Outdoor pool, pool loungers

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
The price is ₹11,965
₹16,152 total
includes taxes & fees
3 Aug - 4 Aug
La Jolla Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,014 reviews)
  • cleanliness
    Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
The price is ₹11,159
₹15,909 total
includes taxes & fees
5 Aug - 6 Aug
Drop Anchor
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,088 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is ₹24,964
₹34,540 total
includes taxes & fees
18 Aug - 19 Aug
Islander Resort
View from property

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,435 reviews)
  • cleanliness
    A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
The price is ₹11,484
₹17,233 total
includes taxes & fees
17 Aug - 18 Aug
Lime Tree Bay Resort
Outdoor pool, pool loungers

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
The price is ₹14,785
₹23,627 total
includes taxes & fees
26 Aug - 27 Aug
La Siesta Resort & Villas
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (713 reviews)
  • cleanliness
    Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
The price is ₹9,727
₹12,469 total
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, (1,001 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is ₹10,488
₹14,920 total
includes taxes & fees
13 Aug - 14 Aug
Fisher Inn 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.
View all properties

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, (1744)
The price is ₹14,447
₹21,633 total
includes taxes & fees
3 Aug - 4 Aug
Chesapeake Beach Resort
View all properties

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, (1364)
The price is ₹14,063
₹22,815 total
includes taxes & fees
12 Aug - 13 Aug
Cheeca Lodge & Spa
View all properties

4-star hotels with pools in Islamorada

Room, 1 King Bed with Sofa bed, Oceanfront (Alligator Reef, Lanai) | View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1313)
The price is ₹14,950
₹23,814 total
includes taxes & fees
19 Aug - 20 Aug
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.
View all properties

Top Islamorada Hotel Reviews

Drop Anchor

Drop Anchor

10/10 Excellent
"Fue una experience inolvidable gracias a todos el equipo de trabajo en especial a quien me recibio no recuerdo su nombre pero fue muy agradable y me ayudo en todo lo que necesitaba 10/10"
Cesarina 3-night trip
Posted 15 hours ago
Drop Anchor

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 Islamorada Brewery & Distillery and Florida Keys Brewing Co., 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?
Make a point to visit attractions such as Founders Park and MoradaWay Arts & Cultural District. Discover sights such as Islamorada Brewery & Distillery, Florida Keys Brewing Co. and Bud n' Mary's Dive Center during your stay. 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.