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

Islamorada Hotels with Swimming Pool

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Check availability on Islamorada Hotels with Swimming Pools

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 bar area with a wooden counter, bar stools, and potted plants.
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.

1. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
RM1,168
RM1,612 total
includes taxes & fees
27 Oct - 28 Oct
Islander Resort
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
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.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
RM616
RM923 total
includes taxes & fees
5 Oct - 6 Oct
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 hotel room with a large bed, a television, a dining area with chairs, a table, 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.

3. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
RM608
RM982 total
includes taxes & fees
4 Oct - 5 Oct
Cheeca Lodge & Spa
A resort pool with palm trees, beach chairs, and umbrellas.
A balcony with a view of a beach, palm trees, and a pool.
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.

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.
RM631
RM1,008 total
includes taxes & fees
4 Oct - 5 Oct
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 wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
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.

5. 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.
RM608
RM684 total
includes taxes & fees
4 Oct - 5 Oct
Coconut Cove Resort and Marina
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 wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

6. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
RM395
RM559 total
includes taxes & fees
6 Oct - 7 Oct
La Jolla Resort
A resort with a pool, beach, and ocean view.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A seaside resort with a glass balustrade, outdoor seating, and a mural of tropical leaves.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
  • Sparkling pools welcome island adventurers to this oceanfront sanctuary with marina access and private beach lounging areas.
RM878
RM1,286 total
includes taxes & fees
18 Oct - 19 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
An aerial view of a resort with a swimming pool, palm trees, and a dock extending into the water.
A beachside resort with a pool area, lounge chairs, and palm trees.
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.
Room

8. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
RM841
RM1,171 total
includes taxes & fees
15 Oct - 16 Oct
Pines & Palms 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 covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

9. 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.
RM551
RM754 total
includes taxes & fees
12 Oct - 13 Oct
Fisher Inn Resort & Marina
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.
A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.
A balcony with a view of the beach, lounge chairs, and a palm tree.

10. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
  • Dive into coastal bliss with a private beach, marina, and refreshing pool for aquatic adventures.
RM551
RM754 total
includes taxes & fees
18 Oct - 19 Oct
Hadley 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 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.
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
RM616
RM923 total
includes taxes & fees
5 Oct - 6 Oct
Chesapeake Beach Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.
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
RM878
RM1,286 total
includes taxes & fees
18 Oct - 19 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 wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
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

Coconut Cove Resort and Marina
Islamorada
RM608
RM684 total
includes taxes & fees
4 Oct - 5 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.
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.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
RM551
RM754 total
includes taxes & fees
12 Oct - 13 Oct
Fisher Inn Resort & Marina
A balcony with a view of a beach, a pool, and a thatched-roof structure.
An aerial view of a marina with docked boats, a building with balconies, and a beach area.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.
A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
RM551
RM754 total
includes taxes & fees
18 Oct - 19 Oct
Hadley Resort and Marina
A wooden deck with a view of the ocean and a palm tree.
A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious interior with a high ceiling, large windows, and a central chandelier.
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
RM1,134
RM1,501 total
includes taxes & fees
12 Oct - 13 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.
Room
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

Coconut Palm Inn

Coconut Palm Inn
Tavernier
RM767
RM1,024 total
includes taxes & fees
5 Oct - 6 Oct
Coconut Palm Inn
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A hotel room with a bed, a TV, a sofa, and a balcony with a 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
RM400
RM580 total
includes taxes & fees
8 Oct - 9 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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 beachside patio with lounge chairs, a table, and a view of the ocean.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
RM1,073
RM1,432 total
includes taxes & fees
15 Oct - 16 Oct
Playa Largo Resort & Spa, Autograph Collection
A covered outdoor area with a pool, palm trees, and a wooden deck.
A building with a colorful fish mural on the wall, a door, and a window.
A hotel room with a large bed, a desk with a television, a chair, a desk lamp, and a window with curtains.
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.

Key Largo Inn

Key Largo Inn
Key Largo
RM437
RM492 total
includes taxes & fees
4 Oct - 5 Oct
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 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.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
RM608
RM982 total
includes taxes & fees
4 Oct - 5 Oct
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 wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
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

Coconut Cove Resort and Marina
Islamorada
RM608
RM684 total
includes taxes & fees
4 Oct - 5 Oct
Coconut Cove Resort and Marina
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
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
RM2,130
RM2,664 total
includes taxes & fees
13 Oct - 14 Oct
The Islands of Islamorada
A wooden deck with a view of the ocean and a palm tree.
A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious interior with a high ceiling, large windows, and a central chandelier.
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
RM1,134
RM1,501 total
includes taxes & fees
12 Oct - 13 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 hotel room with a bed, a TV, a sofa, and a balcony with a 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
RM400
RM580 total
includes taxes & fees
8 Oct - 9 Oct
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 clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.
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.

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
RM1,037
RM1,281 total
includes taxes & fees
2 Oct - 3 Oct
Kona Kai Resort and Gallery - Adults Only
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 beachside patio with lounge chairs, a table, and a view of the ocean.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
RM1,073
RM1,432 total
includes taxes & fees
15 Oct - 16 Oct
Playa Largo Resort & Spa, Autograph Collection
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 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.

Bahia Bay Resort

Bahia Bay Resort
Rock Harbor
RM621
RM698 total
includes taxes & fees
2 Oct - 3 Oct
Bahia Bay Resort
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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 bar area with a wooden counter, bar stools, and potted plants.
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.

Islander Resort

Islander Resort
Matecumbe
RM1,168
RM1,612 total
includes taxes & fees
27 Oct - 28 Oct
Islander 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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
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
RM631
RM1,008 total
includes taxes & fees
4 Oct - 5 Oct
Amara Cay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.
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
RM878
RM1,286 total
includes taxes & fees
18 Oct - 19 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A wooden deck with a view of the ocean and a palm tree.
A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious interior with a high ceiling, large windows, and a central chandelier.
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
RM1,134
RM1,501 total
includes taxes & fees
12 Oct - 13 Oct
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 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.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
RM1,073
RM1,432 total
includes taxes & fees
15 Oct - 16 Oct
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great place"
Juan 4-night trip
Posted 1 day ago
Chesapeake Beach Resort
Islander Resort

Islander Resort

10/10 Excellent
"It great amenities but pools are small."
Jaily 2-night trip
Posted 2 days ago
Islander Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"First time staying and we enjoyed it"
Pamela 1-night trip
Posted 2 days ago
Hadley Resort and Marina
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 3 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 3 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 6 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 7 days ago
Drop Anchor

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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