Hotels with Swimming Pool, Islamorada Florida

Q: What are some accommodations with pools in Islamorada?

Chesapeake Beach Resort : Features a private beach, 2 outdoor 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.

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Our top choices for Islamorada hotels with a pool

Lime Tree Bay Resort

Long Key

A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.

P14,508 total

includes taxes & fees

May 3 - May 4

Chesapeake Beach Resort

Matecumbe

Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.

P20,059 total

includes taxes & fees

Apr 28 - Apr 29

Cheeca Lodge & Spa

Matecumbe

Tropical paradise swim experience awaits with three refreshing pools and poolside service.

P24,664 total

includes taxes & fees

Apr 29 - Apr 30

Rock Reef Resort

Rock Harbor

Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views.

P13,355 total

includes taxes & fees

Apr 30 - May 1

Ragged Edge Resort & Marina

Islamorada

Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.

P16,329 total

includes taxes & fees

Apr 14 - Apr 15

Treasure Harbor

Islamorada

P21,396 total

includes taxes & fees

Apr 16 - Apr 17

Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Matecumbe

Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.

P22,386 total

includes taxes & fees

Apr 19 - Apr 20

Outdoor pool, open 8:00 AM to 11:00 PM, sun loungers

Ocean Pointe Suites at Key Largo

Tavernier

Tranquil poolside paradise in Key Largo where warm waters meet a private beachfront setting and stunning ocean vistas await.

P13,280 total

includes taxes & fees

Apr 30 - May 1

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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

Matecumbe

P20,059 total

includes taxes & fees

Apr 28 - Apr 29

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Key Largo

P27,459 total

includes taxes & fees

Apr 21 - Apr 22

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

P13,436 total

includes taxes & fees

Apr 30 - May 1

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

P30,355 total

includes taxes & fees

Apr 30 - May 1

In-room safe, individually decorated, individually furnished

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Islamorada

P26,978 total

includes taxes & fees

Apr 30 - May 1

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Hotels with pools and hot tubs in Islamorada

Cheeca Lodge & Spa

Matecumbe

P24,664 total

includes taxes & fees

Apr 29 - Apr 30

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

P13,436 total

includes taxes & fees

Apr 30 - May 1

Kona Kai Resort and Gallery - Adults Only

Rock Harbor

P19,927 total

includes taxes & fees

Apr 5 - Apr 6

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

P30,355 total

includes taxes & fees

Apr 30 - May 1

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Key Largo

P27,459 total

includes taxes & fees

Apr 21 - Apr 22

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4-star hotels with pools in Islamorada

Amara Cay Resort

Matecumbe

P22,386 total

includes taxes & fees

Apr 19 - Apr 20

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Key Largo

P27,459 total

includes taxes & fees

Apr 21 - Apr 22

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

P30,355 total

includes taxes & fees

Apr 30 - May 1

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Islamorada

P26,978 total

includes taxes & fees

Apr 30 - May 1

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Top Islamorada Hotel Reviews

Coconut Cove Resort and Marina

10/10 Excellent

"We absolutely loved it here! Such a relaxing & welcoming vibe. Staff was so amazing and helpful- special shoutout to Crystal (apologies if I misspelled her name), she instantly made us feel right at home and gave us good recommendations on where to go. We only wished we could’ve stayed longer! Certainly will be back asap! Until next time ~xx "

Breezy Palms Resort

10/10 Excellent

"First, the location is excellent! Lovely peaceful spot with a sandy palm studded 'beach' offering Atlantic ocean views of Alligator Reef Lighthouse. Clean rooms, big screen porches, great views from the Oceanside apartments. They had what we needed in the kitchen and bath, but just the basics which was fine. Beds were comfy and the living area was roomy. Boaters enjoy a great dock, grounds have grills and a pool. Lovely spot!"

Chesapeake Beach Resort

8/10 Good

"Good location in Islamorada close to attractions and good midpoint for exploring the keys. The property has the old building, motel style by the road and newer buildings and villas a bit more modern. Breakfast gets a bit backed up so go early if you want omelets, pancakes or French toast (the warm options). There are some continental breakfast options as well. Looks like they are trying to make things more upscale but not quite there yet. They could use some hammocks by the beach, the palm trees are begging for it and some ideas to fill the empty space between old and new buildings. Overall good luck experience, but not wow."

Fisher Inn Resort & Marina

10/10 Excellent

"First off the staff were amazing the woman at the front desk was so helpful and friendly made me feel at home . If you are looking for a great time on the water hit up holf tight charters his boat is conveniently located just steps away from the hotel. The captain is awesome. Rooms were clean and the beds are comfortable "

Frequently asked questions

What's it like visiting Islamorada?

If taking it easy by the pool is your idea of the perfect getaway, you might want to think about relaxing Islamorada, which offers 152 places to stay with pools. During your trip, you can explore sights such as Everglades National Park and Bud n' Mary's Dive Center, and then relax and unwind poolside at one of the accommodations in Islamorada that guests like for their pools.

What are some accommodations with pools in Islamorada?

Chesapeake Beach Resort: Features a private beach, 2 outdoor 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 should I expect to find in Islamorada?

Expedia's 152 hotels in Islamorada give you a great choice for your poolside getaway.

What is there to see and do in Islamorada?

Explore places like 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 into account the local weather in Islamorada is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.

Hotels with Swimming Pool in Islamorada, Florida

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Check availability on Islamorada Hotels with Swimming Pool

Our top choices for Islamorada hotels with a pool

Lime Tree Bay Resort

Chesapeake Beach Resort

Cheeca Lodge & Spa

Rock Reef Resort

Ragged Edge Resort & Marina

Treasure Harbor

Amara Cay Resort

Ocean Pointe Suites at Key Largo

Bayside Inn Key Largo

Islander Resort

Choose what matters most at hotels with a pool in Islamorada

Hotels with pools and free breakfast in Islamorada

Chesapeake Beach Resort

Hotels with pools and hot tubs in Islamorada

Cheeca Lodge & Spa

4-star hotels with pools in Islamorada

Amara Cay Resort

Top Islamorada Hotel Reviews

Coconut Cove Resort and Marina

Frequently asked questions

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