Islamorada Hotels with Swimming Pool

  • 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 Pools

Our top choices for Islamorada hotels with a pool

Terrace/patio
Lime Tree Bay Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,136 reviews)
"Great sunsets, convenient restaurant next door, great staff."
United States
Kris
Lime Tree Bay Resort
Aerial view
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, (1,005 reviews)
"Staff was courteous, room was clean & ready when we arrived. "
United States
Kathy
The price is RM550
RM747 total
includes taxes & fees
25 Jan - 26 Jan
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior detail
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,077 reviews)
"Would stay here again!"
United States
James
Rock Reef Resort
Terrace/patio
Bahia Bay Resort

Bahia Bay Resort

Bahia Bay Resort
2.5 star property
Rock Harbor
8.8 out of 10, Excellent, (130 reviews)
"Friendly, communicative and helpful staff. Clean and organized and peaceful. No jets but relaxing hot tub and lovely view of ocean. "
United States
Andrew
Bahia Bay Resort
Beach/ocean view
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,631 reviews)
"Clean, gorgeous view, amazing free breakfast, loved the robes!"
United States
Devon
The price is RM768
RM1,093 total
includes taxes & fees
28 Jan - 29 Jan
Chesapeake Beach Resort
Outdoor pool
Treasure Harbor

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (124 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor
Exterior
Key Largo Inn

Key Largo Inn

Key Largo Inn
3.0 star property
Key Largo
6.6 out of 10, (1,001 reviews)
"Parking easy safe"
United States
Victoria
Key Largo Inn
Exterior
Bayside Inn Key Largo

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,656 reviews)
"Spotless rooms, staff is so friendly and helpful! Amazing place to stay."
Canada
Jeannie
The price is RM648
RM830 total
includes taxes & fees
15 Jan - 16 Jan
Bayside Inn Key Largo
Outdoor pool, pool loungers
La Jolla Resort

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (1,009 reviews)
"This place is amazing "
United States
cindy
La Jolla Resort
Outdoor pool, open 8:00 AM to 11:00 PM, pool loungers
Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1,011 reviews)
"Affordable nice ocean view from living room and master bedroom nice pool and pickle ball courts great service "
United States
Tong
The price is RM659
RM815 total
includes taxes & fees
20 Jan - 21 Jan
Ocean Pointe Suites at Key Largo
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

Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Balcony view was spectacular! Quite and beautiful Room good! Mattresses could use upgrade and no oven but cook top"
Christine 5-night trip
Posted 3 days ago
Hadley Resort and Marina

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 136 places to stay with pools. During your visit, you can explore sights such as Everglades National Park 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. 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 will I be able to find in Islamorada?
Expedia's 136 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.

Explore a world of travel with Expedia