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 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Islamorada hotels with a pool

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 balcony with a view of palm trees and the sea, a white railing, and a table with chairs.
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
₩265,625
₩396,443 total
includes taxes & fees
Oct 19 - Oct 20
Cheeca Lodge & Spa
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 bar area with a wooden counter, bar stools, and potted plants.

2. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
₩277,638
₩409,945 total
includes taxes & fees
Oct 18 - Oct 19
Islander Resort
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 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.

3. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
₩201,621
₩301,907 total
includes taxes & fees
Oct 18 - Oct 19
Chesapeake Beach 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 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 beach with palm trees, a dock, and lounge chairs.

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.
₩206,327
₩329,732 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
A resort with a pool, beach, and ocean view.
A beach with palm trees, a clear blue sky, and a calm sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

5. 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.
₩319,284
₩456,808 total
includes taxes & fees
Nov 3 - Nov 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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.
Living area
A beach with wooden lounge chairs, palm trees, and a clear view of the ocean.

6. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
₩172,029
₩231,081 total
includes taxes & fees
Oct 15 - Oct 16
La Jolla Resort
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

Fisher Inn Resort & Marina
Islamorada
  • Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
₩215,036
₩285,470 total
includes taxes & fees
Nov 8 - Nov 9
Fisher Inn Resort & Marina
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 beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

8. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
  • Luxurious beachfront escape offers dual pools, hot tub, and tropical cocktails steps from the shore.
₩696,766
₩871,377 total
includes taxes & fees
Oct 15 - Oct 16
The Islands of Islamorada
A resort with a pool surrounded by palm trees and a view of the ocean.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A row of colorful beach huts with palm trees in the background.
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.
₩224,347
₩350,005 total
includes taxes & fees
Nov 8 - Nov 9
La Siesta Resort & Villas
An aerial view of a resort with a swimming pool, palm trees, and a dock extending into the water.
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.
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.

10. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
₩275,102
₩383,078 total
includes taxes & fees
Oct 15 - Oct 16
Pines & 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 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.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
₩201,621
₩301,907 total
includes taxes & fees
Oct 18 - Oct 19
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 beach with palm trees, a thatched-roof hut, and lounge 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 beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
₩198,885
₩223,745 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.
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

Fisher Inn Resort & Marina
Islamorada
₩215,036
₩285,470 total
includes taxes & fees
Nov 8 - Nov 9
Fisher Inn Resort & Marina
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
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.
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
₩319,284
₩456,808 total
includes taxes & fees
Nov 3 - Nov 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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 resort with a pool, multiple buildings, and a waterfront 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
₩142,957
₩203,153 total
includes taxes & fees
Oct 15 - Oct 16
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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
₩191,010
₩258,441 total
includes taxes & fees
Nov 9 - Nov 10
Hadley Resort and Marina
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

Coconut Palm Inn
Tavernier
₩251,076
₩335,024 total
includes taxes & fees
Oct 15 - Oct 16
Coconut Palm Inn
An aerial view of a resort with a large pool, palm trees, and a beach.
A beachside patio with lounge chairs, a table, and a view of the ocean.
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
₩351,052
₩468,522 total
includes taxes & fees
Nov 1 - Nov 2
Playa Largo Resort & Spa, Autograph Collection
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 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 spacious interior with a high ceiling, large windows, and a central chandelier.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
₩392,938
₩515,644 total
includes taxes & fees
Oct 28 - Oct 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 pool area with lounge chairs and a pool, surrounded by a building with multiple balconies and a garden.

Key Largo Inn

Key Largo Inn
Key Largo
₩106,917
₩120,282 total
includes taxes & fees
Oct 15 - Oct 16
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 bar area with a thatched roof, wooden chairs, and a view of the ocean.
A tropical resort with a swimming pool, palm trees, and a waterfall.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
₩265,625
₩396,443 total
includes taxes & fees
Oct 19 - Oct 20
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 beach with palm trees, a thatched-roof hut, and lounge 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 beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
₩198,885
₩223,745 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 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.
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
₩142,957
₩203,153 total
includes taxes & fees
Oct 15 - Oct 16
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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 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.

Bahia Bay Resort

Bahia Bay Resort
Rock Harbor
₩203,023
₩228,401 total
includes taxes & fees
Oct 15 - Oct 16
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
₩237,127
₩304,316 total
includes taxes & fees
Oct 15 - Oct 16
Kona Kai Resort and Gallery - Adults Only
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 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 spacious interior with a high ceiling, large windows, and a central chandelier.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
₩392,938
₩515,644 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 beachside patio with lounge chairs, a table, and a view of the ocean.
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
₩351,052
₩468,522 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.
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 resort pool with palm trees, beach chairs, and umbrellas.

Amara Cay Resort

Amara Cay Resort
Matecumbe
₩206,327
₩329,732 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 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.

Islander Resort

Islander Resort
Matecumbe
₩277,638
₩409,945 total
includes taxes & fees
Oct 18 - Oct 19
Islander Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
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.
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
₩319,284
₩456,808 total
includes taxes & fees
Nov 3 - Nov 4
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 beach resort with palm trees, a thatched hut, and a purple building with a window.
A row of colorful beach huts with palm trees in the background.
A resort with a pool surrounded by palm trees and a view of the ocean.

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
₩224,347
₩350,005 total
includes taxes & fees
Nov 8 - Nov 9
La Siesta Resort & Villas
An aerial view of a resort with a large pool, palm trees, and a beach.
A beachside patio with lounge chairs, a table, and a view of the ocean.
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
₩351,052
₩468,522 total
includes taxes & fees
Nov 1 - Nov 2
Playa Largo Resort & Spa, Autograph Collection
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 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 spacious interior with a high ceiling, large windows, and a central chandelier.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
₩392,938
₩515,644 total
includes taxes & fees
Oct 28 - Oct 29
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

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

8/10 Good
"Open the bar and restaurant"
Thomas 2-night trip
Posted 3 hours ago
Coconut Cove Resort and Marina
Amara Cay Resort

Amara Cay Resort

8/10 Good
"Hallways quite loud in the mornings by staff, like they forget people are on vacation and sleeping. Pool itself is nice. Sand is very rocky so must wear shoes."
Kristen 4-night trip
Posted 6 hours ago
Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"10/10 recommend!"
Jessica 3-night trip
Posted 7 hours ago
Chesapeake Beach Resort
La Jolla Resort

La Jolla Resort

10/10 Excellent
"It was quaint and right on the water"
Julie 1-night trip
Posted 8 hours ago
La Jolla Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10"
Sadie 9-night trip
Posted 1 day ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"Clean and spacious. Good location for what I wanted. Loved the mini kitchen inside."
cora 3-night trip
Posted 1 day ago
Breezy Palms Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"It was EXACTLY what I was looking for. Thank you! I wish I had more time to enjoy the super adorable room."
Lynille 1-night trip
Posted 2 days ago
Fisher Inn Resort & Marina
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"This was an absolute dream vacation for my husband and I. The amenities were fantastic and the property was immaculate. The staff were exceedingly concerned about our comfort and asking if we needed anything. The location couldn’t have been better. We will be back."
Steven Allen 3-night trip
Posted 3 days ago
Pines & Palms Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Great place for the money!"
Nicholas 2-night trip
Posted 10 days ago
Hadley Resort and Marina

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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