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

Find Hotels with a Pool in Islamorada, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Islamorada Hotels with a Pool

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
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 beachside patio with wooden furniture, a thatched roof, 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.
NT$5,572
NT$8,649 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.
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 balcony with a view of palm trees and the sea, a white railing, and a table with chairs.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
NT$6,477
NT$9,667 total
includes taxes & fees
Nov 19 - Nov 20
Cheeca Lodge & Spa
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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A beach with palm trees and lounge chairs.

3. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
NT$4,917
NT$7,362 total
includes taxes & fees
Nov 3 - Nov 4
Chesapeake Beach Resort
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
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.

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.
NT$5,471
NT$8,535 total
includes taxes & fees
Nov 15 - Nov 16
Amara Cay Resort
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.
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.
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

5. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
NT$4,658
NT$6,156 total
includes taxes & fees
Oct 25 - Oct 26
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 beach with palm trees, a clear blue sky, and a calm sea.
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

6. 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.
NT$7,786
NT$11,139 total
includes taxes & fees
Nov 2 - Nov 3
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
A resort with thatched-roof structures, palm trees, and a sandy beach area.

7. 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.
NT$4,850
NT$5,456 total
includes taxes & fees
Oct 26 - Oct 27
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 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 modern hotel room with a balcony, a bed, a TV, and a dining area with chairs and a table.

8. 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.
NT$4,832
NT$6,494 total
includes taxes & fees
Oct 29 - Oct 30
Fisher Inn Resort & Marina
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.
Room
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

9. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
NT$6,223
NT$8,796 total
includes taxes & fees
Nov 1 - Nov 2
Pines & Palms Resort
A pool area with lounge chairs and a sign indicating a drop-off zone.
A view from a window overlooking a beach with palm trees, a wooden deck, and lounge chairs.
A beach with palm trees, a thatched umbrella, and lounge chairs.
A beach with palm trees, a thatched-roof hut, and beach chairs.

10. Drop Anchor

Drop Anchor
Islamorada
  • Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
NT$3,737
NT$5,344 total
includes taxes & fees
Oct 26 - Oct 27
Drop Anchor
View all properties

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 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.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
NT$4,917
NT$7,362 total
includes taxes & fees
Nov 3 - Nov 4
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
NT$4,850
NT$5,456 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.
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.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
NT$4,832
NT$6,494 total
includes taxes & fees
Oct 29 - Oct 30
Fisher Inn Resort & Marina
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 resort with a pool, beach, and ocean view.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
NT$7,786
NT$11,139 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 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.
An aerial view of a marina with docked boats, a building with balconies, and a beach area.

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
NT$4,524
NT$6,152 total
includes taxes & fees
Oct 25 - Oct 26
Hadley Resort and Marina
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.
A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
NT$3,548
NT$5,023 total
includes taxes & fees
Oct 25 - Oct 26
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A wooden deck with white railings, outdoor seating, and a view of the sea with palm trees.
A bedroom with a bed, pillows, a nightstand, a lamp, a mirror, and a door.
A living room with a sofa, a coffee table, a wicker ottoman, a chair, a dining table, and a kitchen area with a microwave and a hanging light fixture.
A resort with a pool, palm trees, and beach chairs.

Coconut Palm Inn

Coconut Palm Inn
Tavernier
NT$6,122
NT$8,170 total
includes taxes & fees
Oct 25 - Oct 26
Coconut Palm 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 beach with lounge chairs and a pier extending into the water.
A modern kitchen with a large island, wooden cabinets, and a stainless steel refrigerator.
A spacious living room with a pool table, bookshelves, and comfortable seating.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
NT$8,781
NT$11,673 total
includes taxes & fees
Nov 9 - Nov 10
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 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.

Key Largo Inn

Key Largo Inn
Key Largo
NT$3,486
NT$3,922 total
includes taxes & fees
Oct 25 - Oct 26
Key Largo Inn
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 beachside patio with lounge chairs, a table, and a view of the ocean.
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
NT$9,862
NT$12,890 total
includes taxes & fees
Nov 9 - Nov 10
Playa Largo Resort & Spa, Autograph Collection
View all properties

Hotels with pools and hot tubs in Islamorada

A bathroom with a large bathtub, a view of the sea, and a pier with boats.
A tropical resort with a swimming pool, palm trees, and a waterfall.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
NT$6,477
NT$9,667 total
includes taxes & fees
Nov 19 - Nov 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 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
NT$4,850
NT$5,456 total
includes taxes & fees
Oct 26 - Oct 27
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.
An aerial view of a resort with multiple bungalow-style buildings, a central swimming pool, and a beach area.
A pool area with clear blue water, white lounge chairs, and palm trees.

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
NT$16,991
NT$21,248 total
includes taxes & fees
Oct 26 - Oct 27
The Islands of Islamorada
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.
A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
NT$3,548
NT$5,023 total
includes taxes & fees
Oct 25 - Oct 26
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
A beach with lounge chairs and a pier extending into the water.
A modern kitchen with a large island, wooden cabinets, and a stainless steel refrigerator.
A spacious living room with a pool table, bookshelves, and comfortable seating.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
NT$8,781
NT$11,673 total
includes taxes & fees
Nov 9 - Nov 10
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 beachside patio with lounge chairs, a table, and a view of the ocean.
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
NT$9,862
NT$12,890 total
includes taxes & fees
Nov 9 - Nov 10
Playa Largo Resort & Spa, Autograph Collection
A tropical resort with a clear pool, palm trees, and lounge chairs.
A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.
A beachside resort with lounge chairs, a pool, and palm trees.
A beach with palm trees, a thatched-roof structure, and kayaks.

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
NT$3,364
NT$4,700 total
includes taxes & fees
Oct 25 - Oct 26
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 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.

Bahia Bay Resort

Bahia Bay Resort
Rock Harbor
NT$4,951
NT$5,570 total
includes taxes & fees
Oct 25 - Oct 26
Bahia Bay Resort
View all properties

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 beachside patio with wooden furniture, a thatched roof, 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
NT$5,572
NT$8,649 total
includes taxes & fees
Nov 15 - Nov 16
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.
A resort pool with palm trees, beach chairs, and umbrellas.
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.

Amara Cay Resort

Amara Cay Resort
Matecumbe
NT$5,471
NT$8,535 total
includes taxes & fees
Nov 15 - Nov 16
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 resort with a pool, beach, and ocean view.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
NT$7,786
NT$11,139 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 beach resort with palm trees, a thatched hut, and a purple building with a window.
A beach with colorful buildings, kayaks, and lounge chairs.
A resort with a pool surrounded by palm trees and a view of the ocean.

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
NT$5,031
NT$8,040 total
includes taxes & fees
Nov 15 - Nov 16
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 beach with lounge chairs and a pier extending into the water.
A modern kitchen with a large island, wooden cabinets, and a stainless steel refrigerator.
A spacious living room with a pool table, bookshelves, and comfortable seating.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
NT$8,781
NT$11,673 total
includes taxes & fees
Nov 9 - Nov 10
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 beachside patio with lounge chairs, a table, and a view of the ocean.
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
NT$9,862
NT$12,890 total
includes taxes & fees
Nov 9 - Nov 10
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

Islander Resort

Islander Resort

8/10 Good
"The place is beautiful. Staff is great. Unfortunately the high-end restaurant has a very poorly flavored food. The foor portions are ridiculously small, and the prices are extremely high. I would recommend eating elsewhere or in the bar."
Jorge 1-night trip
Posted less than an hour ago
Islander Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

8/10 Good
"Very clean very quiet Close to nice restaurants and bars"
Jose 1-night trip
Posted 4 hours ago
Fisher Inn Resort & Marina
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"We had a great stay here. The front desk staff greeted us with genuine warmth and made the check-in process completely seamless. The room was spotless, quiet, and very comfortable. The housekeeping team worked had to keep everything fresh and well-maintained. The bed was comfortable, and the bathroom had a great shower with quality toiletries. The range of amenities really stood out, from the reliable high-speed Wi-Fi and well-equipped fitness center to the breakfast options available in the morning. We would happily stay here again!"
Aaron 3-night trip
Posted 5 hours ago
Amara Cay Resort
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"We stayed at one of the bungalows which were very new, cozy and comfortable. It had 3 bedrooms which was perfect for us!"
Karin 1-night trip
Posted 9 hours ago
Pines & Palms Resort
Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"Right on the ocean. Beautiful views. Very relaxing. Not busy this time of year and it was great."
Judy 3-night trip
Posted 1 day ago
Breezy Palms Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Can’t wait to stay again in the spring. Amazing property."
Jason 1-night trip
Posted 2 days ago
Hadley Resort and Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Our stay here was wonderful. Though some things may need updated the overall ambiance of the resort over rode that. The managing staff are very helpful & hardworking. It’s a beautiful piece of oceanfront property & so easy to navigate whether you want to swim, boat, fish or just relax."
louise 8-night trip
Posted 2 days ago
Coconut Cove Resort and Marina
Casa Morada

Casa Morada

10/10 Excellent
"."
angela 3-night trip
Posted 6 days ago
Casa Morada
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Muy bien todo excelente servicio"
Rodolfo 4-night trip
Posted 3 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.

Explore a world of travel with Expedia