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

Search Hotels with Swimming 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 Swimming Pool

Tonight
13 Sept - 14 Sept
Tomorrow
14 Sept - 15 Sept
Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept

Our top choices for Islamorada hotels with a pool

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A 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 balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
₹14,434
₹21,614 total
includes taxes & fees
14 Sept - 15 Sept
Chesapeake Beach 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.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

2. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
₹10,023
₹13,964 total
includes taxes & fees
27 Sept - 28 Sept
La Jolla 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 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.

3. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
₹14,238
₹23,007 total
includes taxes & fees
15 Sept - 16 Sept
Cheeca Lodge & Spa
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.
₹13,589
₹22,276 total
includes taxes & fees
21 Sept - 22 Sept
Amara Cay Resort
A nighttime swimming pool with a blue tint, surrounded by palm trees and a fenced area with lounge chairs.
A beach with thatched umbrellas, palm trees, and lounge chairs.
A beach with palm trees, thatched-roof huts, and lounge chairs.
A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

5. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
  • Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
₹7,895
₹10,406 total
includes taxes & fees
15 Sept - 16 Sept
Breezy Palms 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 beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A wooden pier leading to a beach with palm trees and a row of beach huts.

6. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
₹20,352
₹29,346 total
includes taxes & fees
21 Sept - 22 Sept
Islander 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 deck with two blue chairs and a white table, overlooking a body of water and palm trees.
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

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.
₹11,290
₹15,820 total
includes taxes & fees
21 Sept - 22 Sept
Fisher Inn Resort & Marina
A resort with a pool, beach, and ocean view.
A seaside resort with a glass balustrade, outdoor seating, and a mural of tropical leaves.
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.

8. 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.
₹17,506
₹26,683 total
includes taxes & fees
20 Sept - 21 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.
A marina with a boat docked at a wooden pier, surrounded by palm trees and buildings.
A wooden deck with a thatched roof, wooden railings, and yellow chairs.
A beach pathway with palm trees, a lifeguard tower, and the ocean in the background.

9. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
  • Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
₹7,934
₹8,925 total
includes taxes & fees
20 Sept - 21 Sept
Ragged Edge Resort & Marina
A resort with a swimming pool, lounge chairs, and palm trees.
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.
A spacious living area with a large island, wooden furniture, and a ceiling fan.

10. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
  • A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
₹9,945
₹19,311 total
includes taxes & fees
16 Sept - 17 Sept
Lime Tree Bay 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 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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
₹14,434
₹21,614 total
includes taxes & fees
14 Sept - 15 Sept
Chesapeake Beach Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A coastal resort with a beach, a swimming pool, and multiple buildings.
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.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
₹17,506
₹26,683 total
includes taxes & fees
20 Sept - 21 Sept
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 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 resort with thatched-roof structures, palm trees, and a sandy beach area.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
₹14,238
₹16,018 total
includes taxes & fees
14 Sept - 15 Sept
Coconut Cove Resort and Marina
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.
A hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.
A 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
₹11,290
₹15,820 total
includes taxes & fees
21 Sept - 22 Sept
Fisher Inn Resort & Marina
Two Adirondack chairs on a sandy beach with a wooden pier extending into calm water.
A dining area with a wooden table, woven placemats, and chairs.
A bedroom with a bed, a television, a dresser, and a door.
A poolside area with lounge chairs and umbrellas, surrounded by palm trees.

Coconut Palm Inn

Coconut Palm Inn
Tavernier
₹17,975
₹23,985 total
includes taxes & fees
14 Sept - 15 Sept
Coconut Palm Inn
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 beach with clear water, a wooden pier, and lounge chairs under a tree.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
₹24,367
₹32,682 total
includes taxes & fees
27 Sept - 28 Sept
Playa Largo Resort & Spa, Autograph Collection
A hammock on a sandy beach with a view of the sea and a tree overhead.
A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.
A spacious interior with a high ceiling, large windows, and a central chandelier.
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
₹22,646
₹30,744 total
includes taxes & fees
28 Sept - 29 Sept
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A balcony with a view of a beach, a pool, and a thatched-roof structure.
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.
A beach scene with two yellow beach chairs and a person lying on one.

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
₹11,696
₹16,277 total
includes taxes & fees
15 Sept - 16 Sept
Hadley 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 paved pathway leading to a body of water, surrounded by lush greenery and palm trees.
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
₹9,374
₹13,576 total
includes taxes & fees
20 Sept - 21 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A covered outdoor area with a pool, palm trees, and a wooden deck.
A pool area with lounge chairs and a pool, surrounded by a building with multiple balconies and a garden.
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.

Key Largo Inn

Key Largo Inn
Key Largo
₹13,674
₹15,385 total
includes taxes & fees
18 Sept - 19 Sept
Key Largo Inn
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 hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
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.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
₹14,238
₹23,007 total
includes taxes & fees
15 Sept - 16 Sept
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 resort with thatched-roof structures, palm trees, and a sandy beach area.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
₹14,238
₹16,018 total
includes taxes & fees
14 Sept - 15 Sept
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 paved pathway leading to a body of water, surrounded by lush greenery and palm trees.
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
₹9,374
₹13,576 total
includes taxes & fees
20 Sept - 21 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.
A beachside resort with lounge chairs, a pool, and palm trees.
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
₹12,814
₹17,104 total
includes taxes & fees
14 Sept - 15 Sept
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 beach with clear water, a wooden pier, and lounge chairs under a tree.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
₹24,367
₹32,682 total
includes taxes & fees
27 Sept - 28 Sept
Playa Largo Resort & Spa, Autograph Collection
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 scene with rocky shores, a wooden pier, and calm water.
A coastal property with a grassy lawn, palm trees, and a white fence overlooking the sea.

Bahia Bay Resort

Bahia Bay Resort
Rock Harbor
₹14,534
₹16,351 total
includes taxes & fees
14 Sept - 15 Sept
Bahia Bay Resort
A hammock on a sandy beach with a view of the sea and a tree overhead.
A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.
A spacious interior with a high ceiling, large windows, and a central chandelier.
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
₹22,646
₹30,744 total
includes taxes & fees
28 Sept - 29 Sept
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A 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.

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
₹38,701
₹49,581 total
includes taxes & fees
21 Sept - 22 Sept
The Islands of Islamorada
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
₹13,589
₹22,276 total
includes taxes & fees
21 Sept - 22 Sept
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 beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A wooden pier leading to a beach with palm trees and a row of beach huts.

Islander Resort

Islander Resort
Matecumbe
₹20,352
₹29,346 total
includes taxes & fees
21 Sept - 22 Sept
Islander Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A coastal resort with a beach, a swimming pool, and multiple buildings.
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.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
₹17,506
₹26,683 total
includes taxes & fees
20 Sept - 21 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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 beach with clear water, a wooden pier, and lounge chairs under a tree.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
₹24,367
₹32,682 total
includes taxes & fees
27 Sept - 28 Sept
Playa Largo Resort & Spa, Autograph Collection
A hammock on a sandy beach with a view of the sea and a tree overhead.
A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.
A spacious interior with a high ceiling, large windows, and a central chandelier.
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
₹22,646
₹30,744 total
includes taxes & fees
28 Sept - 29 Sept
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

Islander Resort

Islander Resort

10/10 Excellent
"The room was clean. Pools were great very well maintained."
cayetano william 3-night trip
Posted 2 hours ago
Islander Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"I always stay here with my sisters & mom for our girls trip! Always so relaxing!!"
Alisha 1-night trip
Posted 16 hours ago
Chesapeake Beach Resort
Drop Anchor

Drop Anchor

8/10 Good
"Muy tranquilo"
Moraima 2-night trip
Posted 16 hours ago
Drop Anchor
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Great views"
Steve 2-night trip
Posted 17 hours ago
Hadley Resort and Marina
Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"Have stayed here for the past 5 years which includes over 20 nights. Spacious rooms and clean. Like all the recent upgrades to the rooms."
Daniel 3-night trip
Posted 18 hours ago
Breezy Palms Resort
La Jolla Resort

La Jolla Resort

10/10 Excellent
"This is like an oasis along US 1 on the way down to Key West. We only stayed one night, but, in retrospect, I wish we had stayed a night or two more to take advantage of the amenities like the paddleboards and kayaks. It’s immaculately clean, everyone was so friendly, and the room was great. I can’t recommend this place more. It’s like a throwback to an earlier time, but completely updated. Plenty of restaurants to pick from nearby and the Islamorada Brewery across the street is great, and has a wonderful beer garden out back."
Michael 1-night trip
Posted 1 day ago
La Jolla Resort
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"Loved staying here and would stay again. Staff were so friendly and nice - made you feel like you knew them for years."
Stephen 2-night trip
Posted 2 days ago
Pines & Palms Resort
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Amazing customer service"
Lisandra 1-night trip
Posted 7 days ago
Coconut Cove Resort and Marina
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Excellent place to stay!"
Jose 3-night trip
Posted 3 weeks ago
The Caribbean Resort

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 149 places to stay with pools. During your visit, you can explore sights such as Bud n' Mary's Dive Center and Islamorada County Park, 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 149 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 Islamorada County Park and MoradaWay Arts & Cultural District. Discover sights such as Bud n' Mary's Dive Center, Founders Park and Robbie's of Islamorada 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