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

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Check availability on Islamorada Hotels with a Pool

Tonight
Oct 18 - Oct 19
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Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Islamorada hotels with a pool

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.
A wooden pier leading to a beach with palm trees and a row of beach huts.

1. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
￥30,846
￥46,256 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.
A balcony with a view of palm trees and the sea, a white railing, and a table with chairs.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.
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.
￥29,245
￥44,456 total
includes taxes & fees
Oct 21 - Oct 22
Cheeca Lodge & Spa
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 balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

3. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
￥21,921
￥33,550 total
includes taxes & fees
Oct 20 - Oct 21
Chesapeake Beach Resort
A resort pool with palm trees, beach chairs, and umbrellas.
A hotel room with a sofa, a small round table, a desk with a chair, and a view of the sea through large windows.
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 balcony with a view of a beach, palm trees, and a pool.

4. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
￥23,937
￥38,485 total
includes taxes & fees
Oct 21 - Oct 22
Amara Cay Resort
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 beach with wooden lounge chairs, palm trees, and a clear view of the ocean.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

5. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
￥22,612
￥29,884 total
includes taxes & fees
Oct 22 - Oct 23
La Jolla Resort
A pool area with clear blue water, white lounge chairs, and palm trees.
A balcony with two wooden chairs and a small table, overlooking a beach with palm trees and the ocean.
A balcony with two wooden chairs and a small table, overlooking a beach with palm trees and the ocean.
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

6. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
  • Luxurious beachfront escape offers dual pools, hot tub, and tropical cocktails steps from the shore.
￥75,888
￥95,603 total
includes taxes & fees
Oct 20 - Oct 21
The Islands of Islamorada
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 modern hotel room with a balcony, a bed, a TV, and a dining area with chairs and a table.
A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

7. 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.
￥25,125
￥33,421 total
includes taxes & fees
Oct 19 - Oct 20
Fisher Inn Resort & Marina
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.

8. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
  • Splash into vacation mode at a Florida Keys gem with 24-hour pool access for endless aquatic adventures.
￥23,545
￥26,488 total
includes taxes & fees
Oct 26 - Oct 27
Coconut Cove Resort and Marina
A resort with a pool surrounded by palm trees and a view of the ocean.
A row of colorful beach huts with palm trees in the background.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

9. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
  • Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
￥20,274
￥34,364 total
includes taxes & fees
Nov 16 - Nov 17
La Siesta Resort & Villas
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 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.
A beach with thatched umbrellas, palm trees, and lounge chairs.

10. 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.
￥15,502
￥19,961 total
includes taxes & fees
Oct 19 - Oct 20
Breezy Palms Resort
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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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
￥21,921
￥33,550 total
includes taxes & fees
Oct 20 - Oct 21
Chesapeake Beach 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
￥23,545
￥26,488 total
includes taxes & fees
Oct 26 - Oct 27
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 man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
￥25,125
￥33,421 total
includes taxes & fees
Oct 19 - Oct 20
Fisher Inn Resort & Marina
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 beach with palm trees, a clear blue sky, and a calm sea.
A resort with a pool, beach, and ocean view.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
￥37,798
￥54,078 total
includes taxes & fees
Nov 2 - Nov 3
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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
￥22,612
￥30,595 total
includes taxes & fees
Nov 9 - Nov 10
Hadley Resort and Marina
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
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.
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
￥16,924
￥24,051 total
includes taxes & fees
Oct 26 - Oct 27
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Two Adirondack chairs on a sandy beach with a wooden pier extending into calm water.
A bedroom with a bed, bedside tables, a chair, and artwork on the walls.
A kitchen with wooden cabinets, a black refrigerator, a microwave, and a dining table with chairs.
Four white Adirondack chairs facing a body of water with a clear sky.

Coconut Palm Inn

Coconut Palm Inn
Tavernier
￥29,723
￥39,662 total
includes taxes & fees
Oct 19 - Oct 20
Coconut Palm Inn
A covered outdoor area with a pool, palm trees, and a wooden deck.
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 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
￥15,401
￥17,326 total
includes taxes & fees
Oct 20 - Oct 21
Key Largo Inn
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
A child sitting on a beach with sand toys and a green bucket nearby.
A beachfront hotel with multiple balconies, a pool, and a beach area with lounge chairs.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
￥42,631
￥56,672 total
includes taxes & fees
Oct 28 - Oct 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A beachside patio with lounge chairs, a table, and a view of the ocean.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
￥44,088
￥58,311 total
includes taxes & fees
Nov 1 - Nov 2
Playa Largo Resort & Spa, Autograph Collection
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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 bar area with a thatched roof, wooden chairs, and a view of the ocean.
A hotel room with a large bed, a television, a dining area with chairs, a table, 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

Cheeca Lodge & Spa
Matecumbe
￥29,245
￥44,456 total
includes taxes & fees
Oct 21 - Oct 22
Cheeca Lodge & Spa
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
￥23,545
￥26,488 total
includes taxes & fees
Oct 26 - Oct 27
Coconut Cove Resort and Marina
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
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.
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
￥16,924
￥24,051 total
includes taxes & fees
Oct 26 - Oct 27
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.
A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
￥25,386
￥33,004 total
includes taxes & fees
Oct 19 - Oct 20
Kona Kai Resort and Gallery - Adults Only
A pool area with palm trees and a building with a white roof.
A coastal property with a grassy lawn, palm trees, and a white fence overlooking the sea.
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.

Bahia Bay Resort

Bahia Bay Resort
Rock Harbor
￥23,767
￥26,738 total
includes taxes & fees
Oct 19 - Oct 20
Bahia Bay Resort
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 resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
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
￥75,888
￥95,603 total
includes taxes & fees
Oct 20 - Oct 21
The Islands of Islamorada
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
A child sitting on a beach with sand toys and a green bucket nearby.
A beachfront hotel with multiple balconies, a pool, and a beach area with lounge chairs.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
￥42,631
￥56,672 total
includes taxes & fees
Oct 28 - Oct 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A beachside patio with lounge chairs, a table, and a view of the ocean.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
￥44,088
￥58,311 total
includes taxes & fees
Nov 1 - Nov 2
Playa Largo Resort & Spa, Autograph Collection
View all properties

4-star hotels with pools in Islamorada

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 bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.
A beach with palm trees, a dock, and lounge chairs.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

Amara Cay Resort

Amara Cay Resort
Matecumbe
￥23,937
￥38,485 total
includes taxes & fees
Oct 21 - Oct 22
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.
A wooden pier leading to a beach with palm trees and a row of beach huts.

Islander Resort

Islander Resort
Matecumbe
￥30,846
￥46,256 total
includes taxes & fees
Nov 15 - Nov 16
Islander 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 beach with palm trees, a clear blue sky, and a calm sea.
A resort with a pool, beach, and ocean view.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
￥37,798
￥54,078 total
includes taxes & fees
Nov 2 - Nov 3
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A row of colorful beach huts with palm trees in the background.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A resort with a pool surrounded by palm trees and a view of the ocean.

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
￥20,274
￥34,364 total
includes taxes & fees
Nov 16 - Nov 17
La Siesta Resort & Villas
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
A child sitting on a beach with sand toys and a green bucket nearby.
A beachfront hotel with multiple balconies, a pool, and a beach area with lounge chairs.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
￥42,631
￥56,672 total
includes taxes & fees
Oct 28 - Oct 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A beachside patio with lounge chairs, a table, and a view of the ocean.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
￥44,088
￥58,311 total
includes taxes & fees
Nov 1 - Nov 2
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.
View all properties

Top Islamorada Hotel Reviews

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Pool side bar On the ocean Very clean and friendly"
Ronald 2-night trip
Posted 2 hours ago
Amara Cay Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Room wash clean, bed and pillows very comfortable and staff was friendly. Lots of little ants on the outdoor walkway and stairs but none in the room."
Janell 1-night trip
Posted 2 hours ago
Fisher Inn Resort & Marina
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"We have stayed here multiple times and always have a good stay."
Michael 1-night trip
Posted 17 hours ago
Pines & Palms Resort
Islander Resort

Islander Resort

10/10 Excellent
"Great resort for families with children"
Bryan 4-night trip
Posted 18 hours ago
Islander Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Super el hotel"
Liset 1-night trip
Posted 1 day ago
Chesapeake Beach Resort
Casa Morada

Casa Morada

10/10 Excellent
"."
angela 3-night trip
Posted 1 day ago
Casa Morada
Hadley Resort and Marina

Hadley Resort and Marina

8/10 Good
"Lovely gem of a place and in a great location to explore either direction in the Keys! Helpful and friendly staff! I stayed in the room units closer to the road and next to the main lobby, so I can't compare them to the larger suites or ocean-view spots--which I'm guessing are fancier. The room was decently clean and comfy! Just noting (not complaining), the bathroom was tiny, but it worked fine for 1 person. Had a nice little kitchenette with a mini fridge, microwave, large sink, and coffee pod maker, so it was easy to save restaurant leftovers or keep a few groceries. There's a sweet little spot to sit in loungers or chairs at the end of the marina and soak up some ocean views (east-facing for sunrise is nice). It's just a quick walk to the backside of the property. It wasn't busy during my stay in early Oct., so it was easy to get a chair anytime, but note that there isn't space for more than a few people at a time. There are kayaks and other things you can use (I didn't have the time)."
Elizabeth 1-night trip
Posted 3 days ago
Hadley Resort and Marina
La Jolla Resort

La Jolla Resort

10/10 Excellent
"It was quaint and right on the water"
Julie 1-night trip
Posted 5 days ago
La Jolla Resort
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Muy bien todo excelente servicio"
Rodolfo 4-night trip
Posted 2 weeks ago
The Caribbean Resort

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 125 places to stay with pools. During your trip, you can explore sights such as Bud n' Mary's Dive Center and Robbie's of Islamorada, 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.
How many pool hotels should I expect 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 like 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 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.

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