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

Hotels with Swimming Pool in Islamorada, Florida

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Check availability on Islamorada Hotels with Swimming Pool

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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.
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.
P9,447
P14,146 total
includes taxes & fees
Oct 6 - Oct 7
Chesapeake Beach Resort
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.
Living area
A beach with wooden lounge chairs, palm trees, and a clear view of the ocean.

2. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
P6,055
P8,572 total
includes taxes & fees
Oct 6 - Oct 7
La Jolla Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.
A hotel room with a large bed, a television, a dining area with chairs, a table, 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 bar area with a thatched roof, wooden chairs, and a view of the ocean.

3. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
P9,319
P15,058 total
includes taxes & fees
Oct 4 - Oct 5
Cheeca Lodge & Spa
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 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.

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.
P5,113
P6,750 total
includes taxes & fees
Oct 1 - Oct 2
Breezy Palms Resort
A resort pool with palm trees, beach chairs, and umbrellas.
A balcony with a view of a beach, palm trees, and a pool.
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 beach with palm trees, a dock, and lounge chairs.

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.
P9,668
P15,450 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay 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 beach with palm trees, a thatched-roof hut, and lounge chairs.

6. 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.
P9,319
P10,484 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
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 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.

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.
P8,453
P11,550 total
includes taxes & fees
Oct 12 - Oct 13
Fisher Inn Resort & Marina
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 wooden pier leading to a beach with palm trees and a row of beach huts.
A bar area with a wooden counter, bar stools, and potted plants.

8. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
P17,911
P24,726 total
includes taxes & fees
Oct 27 - Oct 28
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.
A balcony with wicker furniture and a view of the ocean and palm trees.

9. 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.
P7,226
P10,944 total
includes taxes & fees
Oct 4 - Oct 5
Lime Tree Bay Resort
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.
A beach with palm trees, lounge chairs, and a view of the ocean.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.
A covered outdoor area with a view of a beach and palm trees.

10. 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.
P6,326
P7,117 total
includes taxes & fees
Oct 12 - Oct 13
Rock Reef 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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
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
P9,447
P14,146 total
includes taxes & fees
Oct 6 - Oct 7
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 beach with palm trees, a thatched-roof hut, and lounge chairs.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
P9,319
P10,484 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
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 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.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
P8,453
P11,550 total
includes taxes & fees
Oct 12 - Oct 13
Fisher Inn Resort & Marina
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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
P13,459
P19,716 total
includes taxes & fees
Oct 18 - Oct 19
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 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.
A beach scene with two yellow beach chairs and a person lying on one.

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
P8,458
P11,557 total
includes taxes & fees
Oct 1 - Oct 2
Hadley Resort and Marina
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 hotel room with a bed, a TV, a sofa, and a balcony with a view.
A resort with a pool, multiple buildings, and a waterfront view.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
P6,417
P9,202 total
includes taxes & fees
Oct 7 - Oct 8
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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 bathroom with a white vanity, a mirror, a sink, a cabinet, and a towel rack.
Room

Coconut Palm Inn

Coconut Palm Inn
Tavernier
P11,765
P15,698 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Palm Inn
A wooden deck with a view of the ocean and a palm tree.
A spacious dining area with high ceilings, wicker furniture, and large windows.
A hammock on a sandy beach with a view of the sea and a tree overhead.
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.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
P17,386
P23,007 total
includes taxes & fees
Oct 12 - Oct 13
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 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.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
P16,449
P21,953 total
includes taxes & fees
Oct 13 - Oct 14
Playa Largo Resort & Spa, Autograph Collection
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 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 Inn
Key Largo
P5,854
P6,586 total
includes taxes & fees
Oct 1 - Oct 2
Key Largo Inn
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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 spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A tropical resort with a swimming pool, palm trees, and a waterfall.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
P9,319
P15,058 total
includes taxes & fees
Oct 4 - Oct 5
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 beach with palm trees, a thatched-roof hut, and lounge chairs.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
P9,319
P10,484 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
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 hotel room with a bed, a TV, a sofa, and a balcony with a view.
A resort with a pool, multiple buildings, and a waterfront view.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
P6,417
P9,202 total
includes taxes & fees
Oct 7 - Oct 8
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 beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.
A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.
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
P13,237
P16,651 total
includes taxes & fees
Oct 1 - Oct 2
Kona Kai Resort and Gallery - Adults Only
A pool area with palm trees and a building with a white roof.
A spacious interior with a central open area, a balcony with a railing, and a tiled floor.
A wooden deck overlooking clear turquoise water with a backdrop of dense green foliage and a clear blue sky.
A coastal scene with rocky shores, a wooden pier, and calm water.

Bahia Bay Resort

Bahia Bay Resort
Rock Harbor
P8,392
P9,441 total
includes taxes & fees
Oct 1 - Oct 2
Bahia Bay Resort
A wooden deck with a view of the ocean and a palm tree.
A spacious dining area with high ceilings, wicker furniture, and large windows.
A hammock on a sandy beach with a view of the sea and a tree overhead.
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.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
P17,386
P23,007 total
includes taxes & fees
Oct 12 - Oct 13
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
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.

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
P29,833
P37,607 total
includes taxes & fees
Oct 1 - Oct 2
The Islands of Islamorada
An aerial view of a resort with a large pool, palm trees, and a beach.
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.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
P16,449
P21,953 total
includes taxes & fees
Oct 13 - Oct 14
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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.
A resort pool with palm trees, beach chairs, and umbrellas.

Amara Cay Resort

Amara Cay Resort
Matecumbe
P9,668
P15,450 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
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 wooden pier leading to a beach with palm trees and a row of beach huts.
A bar area with a wooden counter, bar stools, and potted plants.

Islander Resort

Islander Resort
Matecumbe
P17,911
P24,726 total
includes taxes & fees
Oct 27 - Oct 28
Islander Resort
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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
P13,459
P19,716 total
includes taxes & fees
Oct 18 - Oct 19
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A wooden deck with a view of the ocean and a palm tree.
A spacious dining area with high ceilings, wicker furniture, and large windows.
A hammock on a sandy beach with a view of the sea and a tree overhead.
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.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
P17,386
P23,007 total
includes taxes & fees
Oct 12 - Oct 13
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 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.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
P16,449
P21,953 total
includes taxes & fees
Oct 13 - Oct 14
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"All the place is amazing but the rooms needs a little be of work to upgrade, and the beach was not as we imagined"
Daniel 3-night trip
Posted 12 hours ago
Cheeca Lodge & Spa
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"First time staying and we enjoyed it"
Pamela 1-night trip
Posted 14 hours ago
Hadley Resort and Marina
Islander Resort

Islander Resort

10/10 Excellent
"Amazing place would definitely recommend"
Steven 2-night trip
Posted 1 day ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

8/10 Good
"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"
Melissa 1-night trip
Posted 2 days ago
Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"Ya’ll just need a microwave."
Nathalee 3-night trip
Posted 2 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Casa Morada

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 5 days ago
Casa Morada
Drop Anchor

Drop Anchor

10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Payman 3-night trip
Posted 6 days ago
Drop Anchor

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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