Hotels with Pool & Resorts in Islamorada from NZ$361

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Check availability on Islamorada Hotels with Pool

Our top choices for Islamorada hotels with a pool

Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (125 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,076 reviews)
"Nice place to spend some time in the Keys conveniently located,clean rooms and helpful staff with excellent views of Bay."
United States
Harry
Rock Reef Resort
Aerial view

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.6 out of 10, Good, (1,004 reviews)
"Staff was courteous, room was clean & ready when we arrived. "
United States
Kathy
The price is NZ$361
includes taxes & fees
27 Jan - 28 Jan
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Beach/ocean view

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,649 reviews)
"Wonderful breakfast with omelettes cooked to order, great pancakes, fresh fruit, etc. very pleasant staff and beautiful beach area."
United States
Kurt
The price is NZ$428
includes taxes & fees
29 Jan - 30 Jan
Chesapeake Beach Resort
Terrace/patio

Bahia Bay Resort

Bahia Bay Resort
2.5 star property
Rock Harbor
8.8 out of 10, Excellent, (132 reviews)
"Very clean and roomy rooms. The pool is warmest pool in Florida. Will be back every year. Thank You Mike!"
United States
Mark
Bahia Bay 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, (1,005 reviews)
"Great"
United States
Kelly
The price is NZ$363
includes taxes & fees
29 Jan - 30 Jan
Drop Anchor
Outdoor pool, pool loungers

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
"This place is amazing "
United States
cindy
La Jolla Resort
Exterior

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 NZ$423
includes taxes & fees
3 Feb - 4 Feb
Bayside Inn Key Largo
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, (1,138 reviews)
"Beautiful resort on the beach and everything was perfect ."
United States
Vinatha
Lime Tree Bay Resort
Private beach, white sand, sun-loungers, beach towels

Bay Harbor Lodge

Bay Harbor Lodge
3.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (664 reviews)
"Staff and Cleanliness - outstanding!"
United States
Jon
The price is NZ$376
includes taxes & fees
26 Jan - 27 Jan
Bay Harbor Lodge
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
Ocean view

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, (1649)
The price is NZ$428
includes taxes & fees
29 Jan - 30 Jan
Chesapeake Beach Resort
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Hotels with pools and ocean views 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, (1649)
The price is NZ$428
includes taxes & fees
29 Jan - 30 Jan
Chesapeake Beach Resort
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Hotels with pools and spa pools in Islamorada

Exterior
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1000)
The price is NZ$1,064
includes taxes & fees
8 Feb - 9 Feb
Playa Largo Resort & Spa, Autograph Collection
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

La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Nice, spacious suite with an amazing waterfront view. The staff was incredibly warm and welcoming. Beautiful heated pool; I didn’t want to get out. The drinks at the tiki bar could’ve been improved. Lovely beachfront and walkable to several restaurants. "
Kalee 1-night trip
Posted 2 days ago
La Siesta Resort & Villas

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.