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

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Check availability on Islamorada Hotels with Pool

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Islamorada hotels with a pool

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A beach with palm trees and lounge chairs.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
Rp2.704.248
Rp4.049.322 total
includes taxes & fees
28 Sept - 29 Sept
Chesapeake Beach Resort
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 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.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
Rp2.667.547
Rp4.310.237 total
includes taxes & fees
29 Sept - 30 Sept
Cheeca Lodge & Spa
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

3. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
Rp1.732.115
Rp2.452.241 total
includes taxes & fees
29 Sept - 30 Sept
La Jolla Resort
A nighttime swimming pool with a blue tint, surrounded by palm trees and a fenced area with lounge chairs.
A beach with palm trees, thatched-roof huts, and lounge chairs.
A beach with thatched umbrellas, palm trees, and lounge chairs.
A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

4. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
  • Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
Rp1.463.570
Rp1.932.271 total
includes taxes & fees
29 Sept - 30 Sept
Breezy Palms Resort
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
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.
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

Amara Cay Resort
Matecumbe
  • Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
Rp2.767.356
Rp4.422.521 total
includes taxes & fees
29 Sept - 30 Sept
Amara Cay Resort
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.
A deck with two blue chairs and a white table, overlooking a body of water and palm trees.
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
A modern hotel room with a balcony, a bed, a TV, and a dining area with chairs and a table.

6. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
  • Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
Rp2.267.415
Rp3.135.017 total
includes taxes & fees
28 Sept - 29 Sept
Fisher Inn Resort & Marina
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A bar area with a wooden counter, bar stools, and potted plants.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

7. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
Rp3.869.856
Rp5.663.605 total
includes taxes & fees
7 Oct - 8 Oct
Islander Resort
A resort with a swimming pool, lounge chairs, and palm trees.
A spacious living area with a large island, wooden furniture, and a ceiling fan.
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

8. Lime Tree Bay Resort

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.
Rp2.070.051
Rp3.135.028 total
includes taxes & fees
28 Sept - 29 Sept
Lime Tree Bay Resort
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.
A beach with palm trees, lounge chairs, and a view of the ocean.
A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.

9. Rock Reef Resort

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.
Rp1.658.713
Rp1.866.052 total
includes taxes & fees
29 Sept - 30 Sept
Rock Reef Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
A resort with thatched-roof structures, palm trees, and a sandy beach area.

10. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
  • Splash into holiday mode at a Florida Keys gem with 24-hour pool access for endless aquatic adventures.
Rp2.667.547
Rp3.000.990 total
includes taxes & fees
6 Oct - 7 Oct
Coconut Cove Resort and Marina
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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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
Rp2.704.248
Rp4.049.322 total
includes taxes & fees
28 Sept - 29 Sept
Chesapeake Beach Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A resort with a pool, beach, and ocean view.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Rp3.709.502
Rp5.482.436 total
includes taxes & fees
6 Oct - 7 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
A resort with thatched-roof structures, palm trees, and a sandy beach area.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
Rp2.667.547
Rp3.000.990 total
includes taxes & fees
6 Oct - 7 Oct
Coconut Cove Resort and Marina
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
A hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.
A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.
A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
Rp2.267.415
Rp3.135.017 total
includes taxes & fees
28 Sept - 29 Sept
Fisher Inn Resort & Marina
An aerial view of a resort with a large pool, palm trees, and a beach.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A beach with clear water, a wooden pier, and lounge chairs under a tree.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
Rp4.708.489
Rp6.284.042 total
includes taxes & fees
11 Oct - 12 Oct
Playa Largo Resort & Spa, Autograph Collection
A balcony with a view of a beach, a pool, and a thatched-roof structure.
A beach scene with two yellow beach chairs and a person lying on one.
A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
Rp2.115.239
Rp2.963.819 total
includes taxes & fees
28 Sept - 29 Sept
Hadley Resort and Marina
A wooden deck with a view of the ocean and a palm tree.
A spacious interior with a high ceiling, large windows, and a central chandelier.
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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
Rp4.695.241
Rp6.269.138 total
includes taxes & fees
30 Sept - 1 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

Coconut Palm Inn

Coconut Palm Inn
Tavernier
Rp3.370.000
Rp4.496.782 total
includes taxes & fees
27 Sept - 28 Sept
Coconut Palm Inn
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A resort with a pool, multiple buildings, and a waterfront view.
A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.
A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
Rp1.757.560
Rp2.545.371 total
includes taxes & fees
4 Oct - 5 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A covered outdoor area with a pool, palm trees, and a wooden deck.
A hotel room with a large bed, a desk with a television, a chair, a desk lamp, and a window with curtains.
A pool area with lounge chairs and a pool, surrounded by a building with multiple balconies and a garden.
A building with a colorful fish mural on the wall, a door, and a window.

Key Largo Inn

Key Largo Inn
Key Largo
Rp1.675.721
Rp1.885.186 total
includes taxes & fees
29 Sept - 30 Sept
Key Largo Inn
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Hotels with pools and hot tubs in Islamorada

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
A resort with thatched-roof structures, palm trees, and a sandy beach area.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
Rp2.667.547
Rp3.000.990 total
includes taxes & fees
6 Oct - 7 Oct
Coconut Cove Resort and Marina
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 tropical resort with a swimming pool, palm trees, and a waterfall.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
Rp2.667.547
Rp4.310.237 total
includes taxes & fees
29 Sept - 30 Sept
Cheeca Lodge & Spa
An aerial view of a resort with a large pool, palm trees, and a beach.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A beach with clear water, a wooden pier, and lounge chairs under a tree.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
Rp4.708.489
Rp6.284.042 total
includes taxes & fees
11 Oct - 12 Oct
Playa Largo Resort & Spa, Autograph Collection
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 gated entrance to a resort with palm trees and a clear sky.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
Rp7.411.842
Rp9.473.461 total
includes taxes & fees
1 Oct - 2 Oct
The Islands of Islamorada
A wooden deck with a view of the ocean and a palm tree.
A spacious interior with a high ceiling, large windows, and a central chandelier.
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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
Rp4.695.241
Rp6.269.138 total
includes taxes & fees
30 Sept - 1 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A resort with a pool, multiple buildings, and a waterfront view.
A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.
A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
Rp1.757.560
Rp2.545.371 total
includes taxes & fees
4 Oct - 5 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A pool area with palm trees and a building with a white roof.
A coastal scene with rocky shores, a wooden pier, and calm water.
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

Bahia Bay Resort
Rock Harbor
Rp2.402.536
Rp2.702.853 total
includes taxes & fees
28 Sept - 29 Sept
Bahia Bay Resort
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.
A beachside resort with lounge chairs, a pool, and palm trees.
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
Rp2.876.117
Rp3.739.243 total
includes taxes & fees
27 Sept - 28 Sept
Kona Kai Resort and Gallery - Adults Only
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4-star hotels with pools in Islamorada

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A resort with a pool, beach, and ocean view.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Rp3.709.502
Rp5.482.436 total
includes taxes & fees
6 Oct - 7 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
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

Amara Cay Resort
Matecumbe
Rp2.767.356
Rp4.422.521 total
includes taxes & fees
29 Sept - 30 Sept
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A bar area with a wooden counter, bar stools, and potted plants.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

Islander Resort

Islander Resort
Matecumbe
Rp3.869.856
Rp5.663.605 total
includes taxes & fees
7 Oct - 8 Oct
Islander Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A beach with clear water, a wooden pier, and lounge chairs under a tree.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
Rp4.708.489
Rp6.284.042 total
includes taxes & fees
11 Oct - 12 Oct
Playa Largo Resort & Spa, Autograph Collection
A wooden deck with a view of the ocean and a palm tree.
A spacious interior with a high ceiling, large windows, and a central chandelier.
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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
Rp4.695.241
Rp6.269.138 total
includes taxes & fees
30 Sept - 1 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"I liked the breakfast. One pool was being worked on and the pool workers helped themselves to the free breakfast. Some of them stood in the coffee and drink area and ate their free breakfast. The tree trimmers took up some of relaxing areas and they were noisy. The cleaning staff and the front desk staff were very good. The breakfast cook was friendly. The spa was hot but no jet action. We probably won’t be coming back. Thanks"
William 3-night trip
Posted 13 hours ago
Chesapeake Beach Resort
Casa Morada

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 18 hours ago
Casa Morada
La Jolla Resort

La Jolla Resort

8/10 Good
"Loved the amenities"
Kayla 1-night trip
Posted 1 day ago
La Jolla Resort
Drop Anchor

Drop Anchor

10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Payman 3-night trip
Posted 2 days ago
Drop Anchor
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"This place was the best place to stay I've ever been ever it is wonderful there's nothing not to like about this place the ocean the pool the people the place everybody's so nice and accommodating they will do anything they can to make sure you're happy it's paradise in paradise I would suggest to stay at this place anytime it would be a mistake not to"
Michael 1-night trip
Posted 3 days ago
Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Excellent stay! Love this place and will definitely be back!"
Hailey Ritch and Patrick 3-night trip
Posted 8 days ago
Coconut Cove 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 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.

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