Islamorada Hotels with Pool, Florida: Islamorada Hotel Guide

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

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16 Oct - 18 Oct

Our top choices for Islamorada hotels with a pool

A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.

Living area

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

A beach with wooden lounge chairs, palm trees, and a clear view of the ocean.

1. La Jolla Resort

Matecumbe

Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.

€122

includes taxes & fees

6 Oct - 7 Oct

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

A beach with palm trees and lounge chairs.

A hotel room with a bed, a bedside table with a lamp, a small table with a basket, a blue and white striped ottoman, and a balcony with a view of palm trees and the ocean.

2. Chesapeake Beach Resort

Matecumbe

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

€201

includes taxes & fees

5 Oct - 6 Oct

A tropical resort with a swimming pool, palm trees, and a waterfall.

A bar area with a thatched roof, wooden chairs, and a view of the ocean.

A balcony with a view of palm trees and the sea, a white railing, and a table with chairs.

A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

3. Cheeca Lodge & Spa

Matecumbe

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

€254

includes taxes & fees

8 Oct - 9 Oct

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

A beach with palm trees, a thatched-roof hut, and lounge chairs.

A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.

A resort with thatched-roof structures, palm trees, and a sandy beach area.

4. Coconut Cove Resort and Marina

Islamorada

Splash into holiday mode at a Florida Keys gem with 24-hour pool access for endless aquatic adventures.

€149

includes taxes & fees

5 Oct - 6 Oct

A resort pool with palm trees, beach chairs, and umbrellas.

A balcony with a view of a beach, palm trees, and a pool.

A beach with palm trees, a dock, and lounge chairs.

A hotel room with a sofa, a small round table, a desk with a chair, and a view of the sea through large windows.

5. Amara Cay Resort

Matecumbe

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

€219

includes taxes & fees

18 Oct - 19 Oct

A nighttime swimming pool with a blue tint, surrounded by palm trees and a fenced area with lounge chairs.

A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

A beach with palm trees, thatched-roof huts, and lounge chairs.

A living room with a sofa, armchair, coffee table, and lamp. There is a dining area with a table and chairs. The room has a kitchen area with a stove and cabinets.

6. Breezy Palms Resort

Matecumbe

Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.

€96

includes taxes & fees

6 Oct - 7 Oct

Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

A modern hotel room with a balcony, a bed, a TV, and a dining area with chairs and a table.

A deck with two blue chairs and a white table, overlooking a body of water and palm trees.

7. Fisher Inn Resort & Marina

Islamorada

Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.

€156

includes taxes & fees

13 Oct - 14 Oct

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

A paved pathway leading to a beach with palm trees and a view of the ocean.

A wooden pier leading to a beach with palm trees and a row of beach huts.

8. Islander Resort

Matecumbe

Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.

€351

includes taxes & fees

27 Oct - 28 Oct

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Choose what matters most at hotels with a pool in Islamorada

Breakfast included

Hot tub

4 stars

5 stars

Spa

Hotels with pools and free breakfast in Islamorada

A beach with palm trees and lounge chairs.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

Chesapeake Beach Resort

Matecumbe

€201

includes taxes & fees

5 Oct - 6 Oct

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

A beach with palm trees, a clear blue sky, and a calm sea.

A resort with a pool, beach, and ocean view.

An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Islamorada

€280

includes taxes & fees

18 Oct - 19 Oct

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

A beach with palm trees, a thatched-roof hut, and lounge chairs.

A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.

A resort with thatched-roof structures, palm trees, and a sandy beach area.

Coconut Cove Resort and Marina

Islamorada

€149

includes taxes & fees

5 Oct - 6 Oct

A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.

A hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.

Fisher Inn Resort & Marina

Islamorada

€156

includes taxes & fees

13 Oct - 14 Oct

A balcony with a view of a beach, a pool, and a thatched-roof structure.

A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

A beach scene with two yellow beach chairs and a person lying on one.

An aerial view of a marina with docked boats, a building with balconies, and a beach area.

Hadley Resort and Marina

Matecumbe

€164

includes taxes & fees

18 Oct - 19 Oct

A wooden deck with a view of the ocean and a palm tree.

A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.

A hammock on a sandy beach with a view of the sea and a tree overhead.

A spacious dining area with high ceilings, wicker furniture, and large windows.

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

Key Largo

€327

includes taxes & fees

14 Oct - 15 Oct

Two Adirondack chairs on a sandy beach with a wooden pier extending into calm water.

A hotel room with a bed, a sofa, a chair, a nightstand, a lamp, and a window.

Room

A bathroom with a white vanity, a mirror, a sink, a cabinet, and a towel rack.

Coconut Palm Inn

Tavernier

€223

includes taxes & fees

5 Oct - 6 Oct

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.

A hotel room with a bed, a TV, a sofa, and a balcony with a view.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

€127

includes taxes & fees

5 Oct - 6 Oct

An aerial view of a resort with a large pool, palm trees, and a beach.

A beach with clear water, a wooden pier, and lounge chairs under a tree.

A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

A beachside patio with lounge chairs, a table, and a view of the ocean.

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

€312

includes taxes & fees

19 Oct - 20 Oct

A covered outdoor area with a pool, palm trees, and a wooden deck.

A pool area with lounge chairs and a pool, surrounded by a building with multiple balconies and a garden.

A building with a sign reading "C&C wood fired eats" and a menu board listing items like wood, fired, eats, drinks, salumi, and fromage.

A hotel room with a large bed, a desk with a television, a chair, a desk lamp, and a window with curtains.

Key Largo Inn

Key Largo

€107

includes taxes & fees

5 Oct - 6 Oct

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Hotels with pools and hot tubs in Islamorada

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

A bar area with a thatched roof, wooden chairs, and a view of the ocean.

A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

Cheeca Lodge & Spa

Matecumbe

€254

includes taxes & fees

8 Oct - 9 Oct

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

A beach with palm trees, a thatched-roof hut, and lounge chairs.

A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.

A resort with thatched-roof structures, palm trees, and a sandy beach area.

Coconut Cove Resort and Marina

Islamorada

€149

includes taxes & fees

5 Oct - 6 Oct

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

A pool area with clear blue water, white lounge chairs, and palm trees.

A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

A gated entrance to a resort with palm trees and a clear sky.

The Islands of Islamorada

Matecumbe

€580

includes taxes & fees

7 Oct - 8 Oct

A wooden deck with a view of the ocean and a palm tree.

A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.

A hammock on a sandy beach with a view of the sea and a tree overhead.

A spacious dining area with high ceilings, wicker furniture, and large windows.

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

Key Largo

€327

includes taxes & fees

14 Oct - 15 Oct

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.

A hotel room with a bed, a TV, a sofa, and a balcony with a view.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

€127

includes taxes & fees

5 Oct - 6 Oct

A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

A beachside resort with lounge chairs, a pool, and palm trees.

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.

Kona Kai Resort and Gallery - Adults Only

Rock Harbor

€186

includes taxes & fees

5 Oct - 6 Oct

An aerial view of a resort with a large pool, palm trees, and a beach.

A beach with clear water, a wooden pier, and lounge chairs under a tree.

A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

A beachside patio with lounge chairs, a table, and a view of the ocean.

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

€312

includes taxes & fees

19 Oct - 20 Oct

A pool area with palm trees and a building with a white roof.

A wooden deck overlooking clear turquoise water with a backdrop of dense green foliage and a clear blue sky.

A spacious interior with a central open area, a balcony with a railing, and a tiled floor.

A coastal property with a grassy lawn, palm trees, and a white fence overlooking the sea.

Bahia Bay Resort

Rock Harbor

€152

includes taxes & fees

5 Oct - 6 Oct

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4-star hotels with pools in Islamorada

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

A paved pathway leading to a beach with palm trees and a view of the ocean.

A wooden pier leading to a beach with palm trees and a row of beach huts.

Islander Resort

Matecumbe

€351

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

An aerial view of a resort with a swimming pool, palm trees, and a dock.

A resort pool with palm trees, beach chairs, and umbrellas.

A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

Amara Cay Resort

Matecumbe

€219

includes taxes & fees

18 Oct - 19 Oct

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

A beach with palm trees, a clear blue sky, and a calm sea.

A resort with a pool, beach, and ocean view.

An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Islamorada

€280

includes taxes & fees

18 Oct - 19 Oct

A wooden deck with a view of the ocean and a palm tree.

A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.

A hammock on a sandy beach with a view of the sea and a tree overhead.

A spacious dining area with high ceilings, wicker furniture, and large windows.

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

Key Largo

€327

includes taxes & fees

14 Oct - 15 Oct

An aerial view of a resort with a large pool, palm trees, and a beach.

A beach with clear water, a wooden pier, and lounge chairs under a tree.

A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

A beachside patio with lounge chairs, a table, and a view of the ocean.

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

€312

includes taxes & fees

19 Oct - 20 Oct

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

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

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

10/10 Excellent

"I liked everything, you have everything in the resort, restaurant, pizzeria, ice cream shop, very good service on the beach, pool. I hope to return very soon."

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent

"Clean"

Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent

"Great place for the money!"

Casa Morada

Casa Morada

10/10 Excellent

"always a favorite!"

Drop Anchor

Drop Anchor

10/10 Excellent

"Exceeded all my expectations, definitely going back. Highly recommend"

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 125 places to stay with pools. During your visit, you can explore sights such as Bud n' Mary's Dive Center and Robbie's of Islamorada, 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.

How many pool hotels will I be able to find in Islamorada?

Expedia's 125 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 Anne's Beach and MoradaWay Arts & Cultural District. Discover sights such as Bud n' Mary's Dive Center, Robbie's of Islamorada and Fiesta Key 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.