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

Search Hotels with Pool in Islamorada

  • 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 Pool

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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 wooden pier leading to a beach with palm trees and a row of beach huts.
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.
฿7,775
฿11,198 total
includes taxes & fees
19 Oct - 20 Oct
Islander 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 bar area with a thatched roof, wooden chairs, 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.
฿6,669
฿9,954 total
includes taxes & fees
18 Oct - 19 Oct
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 beach with palm trees and lounge chairs.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

3. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
฿5,062
฿7,580 total
includes taxes & fees
18 Oct - 19 Oct
Chesapeake Beach Resort
A resort pool with palm trees, beach chairs, and umbrellas.
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
A balcony with a view of a beach, palm trees, and a pool.
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.
฿5,181
฿8,279 total
includes taxes & fees
19 Oct - 20 Oct
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 wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.
Living area

5. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
฿4,813
฿6,361 total
includes taxes & fees
22 Oct - 23 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 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.

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.
฿8,017
฿11,470 total
includes taxes & fees
2 Nov - 3 Nov
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 resort with thatched-roof structures, palm trees, and a sandy beach area.
A beach with palm trees, a thatched-roof hut, and lounge chairs.

7. 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.
฿4,994
฿5,618 total
includes taxes & fees
26 Oct - 27 Oct
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 beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
A modern hotel room with a balcony, a bed, a TV, and a dining area with chairs and a table.
A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

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.
฿5,329
฿7,089 total
includes taxes & fees
18 Oct - 19 Oct
Fisher Inn Resort & Marina
A resort with a pool surrounded by palm trees and a view of the ocean.
A row of colorful beach huts with palm trees in the background.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

9. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
  • Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
฿5,181
฿8,279 total
includes taxes & fees
15 Nov - 16 Nov
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 kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.
A beachside resort with a pool area, lounge chairs, and palm trees.
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

10. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
฿6,907
฿9,619 total
includes taxes & fees
21 Oct - 22 Oct
Pines & Palms Resort
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 balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
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
฿5,062
฿7,580 total
includes taxes & fees
18 Oct - 19 Oct
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 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.
A beach with palm trees, a thatched-roof hut, and lounge chairs.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
฿4,994
฿5,618 total
includes taxes & fees
26 Oct - 27 Oct
Coconut Cove Resort and Marina
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.
A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
฿5,329
฿7,089 total
includes taxes & fees
18 Oct - 19 Oct
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 beach with palm trees, a clear blue sky, and a calm sea.
A resort with a pool, beach, and ocean view.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
฿8,017
฿11,470 total
includes taxes & fees
2 Nov - 3 Nov
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 beach scene with two yellow beach chairs and a person lying on one.
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
฿4,796
฿6,489 total
includes taxes & fees
9 Nov - 10 Nov
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
฿3,589
฿5,101 total
includes taxes & fees
26 Oct - 27 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Two Adirondack chairs on a sandy beach with a wooden pier extending into calm water.
A kitchen with wooden cabinets, a black refrigerator, a microwave, and a dining table with chairs.
A beachfront property with a wooden staircase leading to a white balcony, surrounded by palm trees and tropical plants.
Four white Adirondack chairs facing a body of water with a clear sky.

Coconut Palm Inn

Coconut Palm Inn
Tavernier
฿6,327
฿8,442 total
includes taxes & fees
18 Oct - 19 Oct
Coconut Palm Inn
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 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
฿3,589
฿4,039 total
includes taxes & fees
15 Nov - 16 Nov
Key Largo Inn
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.
A cozy living room with a pool table, a large bookshelf, and comfortable seating.
A child sitting on a beach with sand toys and a green bucket nearby.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
฿9,866
฿12,947 total
includes taxes & fees
29 Oct - 30 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 restaurant with wooden tables and chairs, a bar area, and a view of the sea.
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.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
฿9,351
฿12,367 total
includes taxes & fees
1 Nov - 2 Nov
Playa Largo Resort & Spa, Autograph Collection
View all properties

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 hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
฿6,669
฿9,954 total
includes taxes & fees
18 Oct - 19 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 resort with thatched-roof structures, palm trees, and a sandy beach area.
A beach with palm trees, a thatched-roof hut, and lounge chairs.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
฿4,994
฿5,618 total
includes taxes & fees
26 Oct - 27 Oct
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
฿3,589
฿5,101 total
includes taxes & fees
26 Oct - 27 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 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.
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
฿5,384
฿7,000 total
includes taxes & fees
20 Oct - 21 Oct
Kona Kai Resort and Gallery - Adults Only
A pool area with palm trees and a building with a white roof.
A wooden deck overlooking clear turquoise water with a backdrop of dense green foliage and a clear blue sky.
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
฿5,098
฿5,735 total
includes taxes & fees
18 Oct - 19 Oct
Bahia Bay Resort
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A gated entrance to a resort with palm trees and a clear sky.

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
฿17,557
฿21,957 total
includes taxes & fees
18 Oct - 19 Oct
The Islands of Islamorada
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.
A cozy living room with a pool table, a large bookshelf, and comfortable seating.
A child sitting on a beach with sand toys and a green bucket nearby.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
฿9,866
฿12,947 total
includes taxes & fees
29 Oct - 30 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 restaurant with wooden tables and chairs, a bar area, and a view of the sea.
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.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
฿9,351
฿12,367 total
includes taxes & fees
1 Nov - 2 Nov
Playa Largo Resort & Spa, Autograph Collection
View all properties

4-star hotels with pools in Islamorada

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
A beach with palm trees, a dock, and lounge chairs.
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.

Amara Cay Resort

Amara Cay Resort
Matecumbe
฿5,181
฿8,279 total
includes taxes & fees
19 Oct - 20 Oct
Amara Cay Resort
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 wooden pier leading to a beach with palm trees and a row of beach huts.
A paved pathway leading to a beach with palm trees and a view of the ocean.

Islander Resort

Islander Resort
Matecumbe
฿7,775
฿11,198 total
includes taxes & fees
19 Oct - 20 Oct
Islander 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 beach with palm trees, a clear blue sky, and a calm sea.
A resort with a pool, beach, and ocean view.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
฿8,017
฿11,470 total
includes taxes & fees
2 Nov - 3 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A row of colorful beach huts with palm trees in the background.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A resort with a pool surrounded by palm trees and a view of the ocean.

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
฿5,181
฿8,279 total
includes taxes & fees
15 Nov - 16 Nov
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.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.
A cozy living room with a pool table, a large bookshelf, and comfortable seating.
A child sitting on a beach with sand toys and a green bucket nearby.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
฿9,866
฿12,947 total
includes taxes & fees
29 Oct - 30 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 restaurant with wooden tables and chairs, a bar area, and a view of the sea.
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.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
฿9,351
฿12,367 total
includes taxes & fees
1 Nov - 2 Nov
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

Hadley Resort and Marina

Hadley Resort and Marina

8/10 Good
"Lovely gem of a place and in a great location to explore either direction in the Keys! Helpful and friendly staff! I stayed in the room units closer to the road and next to the main lobby, so I can't compare them to the larger suites or ocean-view spots--which I'm guessing are fancier. The room was decently clean and comfy! Just noting (not complaining), the bathroom was tiny, but it worked fine for 1 person. Had a nice little kitchenette with a mini fridge, microwave, large sink, and coffee pod maker, so it was easy to save restaurant leftovers or keep a few groceries. There's a sweet little spot to sit in loungers or chairs at the end of the marina and soak up some ocean views (east-facing for sunrise is nice). It's just a quick walk to the backside of the property. It wasn't busy during my stay in early Oct., so it was easy to get a chair anytime, but note that there isn't space for more than a few people at a time. There are kayaks and other things you can use (I didn't have the time)."
Elizabeth 1-night trip
Posted 20 hours ago
Hadley Resort and Marina
La Jolla Resort

La Jolla Resort

10/10 Excellent
"It was quaint and right on the water"
Julie 1-night trip
Posted 3 days ago
La Jolla 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 4 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 6 days ago
Pines & Palms Resort
The Caribbean Resort

The Caribbean Resort

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

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 3 weeks ago
Casa Morada

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.

Explore a world of travel with Expedia