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

Hotels with Swimming Pools in Islamorada

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Check availability on Islamorada Hotels with Swimming Pools

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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 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.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
S$272
includes taxes & fees
14 Oct - 15 Oct
Chesapeake Beach 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 balcony with a view of palm trees and the sea, a white railing, and a table with chairs.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
S$274
includes taxes & fees
12 Oct - 13 Oct
Cheeca Lodge & Spa
A resort pool with palm trees, beach chairs, and umbrellas.
A balcony with a view of a beach, palm trees, and a pool.
A beach with palm trees, a dock, and lounge chairs.
A hotel room with a sofa, a small round table, a desk with a chair, and a view of the sea through large windows.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
S$289
includes taxes & fees
21 Oct - 22 Oct
Amara Cay Resort
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.
Living area
A beach with wooden lounge chairs, palm trees, and a clear view of the ocean.

4. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
S$199
includes taxes & fees
18 Oct - 19 Oct
La Jolla Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A wooden pier leading to a beach with palm trees and a row of beach huts.
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.

5. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
S$470
includes taxes & fees
20 Oct - 21 Oct
Islander Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A resort with thatched-roof structures, palm trees, and a sandy beach area.

6. 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.
S$215
includes taxes & fees
26 Oct - 27 Oct
Coconut Cove Resort and Marina
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 modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.
A living room with a sofa, armchair, coffee table, and lamp. There is a dining area with a table and chairs. The room has a kitchen area with a stove and cabinets.

7. 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.
S$169
includes taxes & fees
21 Oct - 22 Oct
Breezy Palms Resort
A resort with a pool, beach, and ocean view.
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.
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.
S$435
includes taxes & fees
14 Oct - 15 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A resort with a swimming pool, lounge chairs, and palm trees.
Terrace/patio
A spacious living area with a large island, wooden furniture, and a ceiling fan.
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

9. 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.
S$236
includes taxes & fees
12 Oct - 13 Oct
Lime Tree Bay Resort
A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.
A beach pathway with palm trees, a lifeguard tower, and the ocean in the background.
Three Adirondack chairs facing a sunset over a body of water.
A wooden deck with a thatched roof, wooden railings, and yellow chairs.

10. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
  • Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
S$194
includes taxes & fees
11 Oct - 12 Oct
Ragged Edge Resort & Marina
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Choose what matters most at hotels with a pool in Islamorada

Breakfast included
Hot tub
4 stars
5 stars
Spa

Hotels with pools and free breakfast in Islamorada

A beach with palm trees and lounge chairs.
A 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 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
S$272
includes taxes & fees
14 Oct - 15 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 beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A resort with thatched-roof structures, palm trees, and a sandy beach area.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
S$215
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 hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.
A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.
A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
S$274
includes taxes & fees
8 Nov - 9 Nov
Fisher Inn Resort & 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
S$182
includes taxes & fees
14 Oct - 15 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A balcony with a view of a beach, a pool, and a thatched-roof structure.
An aerial view of a marina with docked boats, a building with balconies, and a beach area.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.
A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
S$248
includes taxes & fees
9 Nov - 10 Nov
Hadley Resort and Marina
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.
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
S$435
includes taxes & fees
14 Oct - 15 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.
A bathroom with a white vanity, a mirror, a sink, a cabinet, and a towel rack.

Coconut Palm Inn

Coconut Palm Inn
Tavernier
S$321
includes taxes & fees
11 Oct - 12 Oct
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 beach with clear water, a wooden pier, and lounge chairs under a tree.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
S$450
includes taxes & fees
1 Nov - 2 Nov
Playa Largo Resort & Spa, Autograph Collection
A wooden deck with a view of the ocean and a palm tree.
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 hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious dining area with high ceilings, wicker furniture, and large windows.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
S$471
includes taxes & fees
19 Oct - 20 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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
S$144
includes taxes & fees
20 Oct - 21 Oct
Key Largo Inn
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Hotels with pools and hot tubs in Islamorada

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A 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 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
S$274
includes taxes & fees
12 Oct - 13 Oct
Cheeca Lodge & Spa
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A resort with thatched-roof structures, palm trees, and a sandy beach area.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
S$215
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 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
S$182
includes taxes & fees
14 Oct - 15 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 clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
S$316
includes taxes & fees
19 Oct - 20 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 spacious interior with a central open area, a balcony with a railing, and a tiled floor.
A coastal scene with rocky shores, a wooden pier, and calm water.

Bahia Bay Resort

Bahia Bay Resort
Rock Harbor
S$219
includes taxes & fees
13 Oct - 14 Oct
Bahia Bay Resort
A wooden deck with a view of the ocean and a palm tree.
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 hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious dining area with high ceilings, wicker furniture, and large windows.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
S$471
includes taxes & fees
19 Oct - 20 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
An aerial view of a resort with a large pool, palm trees, and a beach.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A beach with clear water, a wooden pier, and lounge chairs under a tree.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
S$450
includes taxes & fees
1 Nov - 2 Nov
Playa Largo Resort & Spa, Autograph Collection
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A gated entrance to a resort with palm trees and a clear sky.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
S$782
includes taxes & fees
14 Oct - 15 Oct
The Islands of Islamorada
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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 resort pool with palm trees, beach chairs, and umbrellas.
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
S$289
includes taxes & fees
21 Oct - 22 Oct
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A wooden pier leading to a beach with palm trees and a row of beach huts.
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.

Islander Resort

Islander Resort
Matecumbe
S$470
includes taxes & fees
20 Oct - 21 Oct
Islander Resort
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.
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
S$435
includes taxes & fees
14 Oct - 15 Oct
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 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 beach with colorful buildings, kayaks, and lounge chairs.

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
S$336
includes taxes & fees
8 Nov - 9 Nov
La Siesta Resort & Villas
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 beach with clear water, a wooden pier, and lounge chairs under a tree.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
S$450
includes taxes & fees
1 Nov - 2 Nov
Playa Largo Resort & Spa, Autograph Collection
A wooden deck with a view of the ocean and a palm tree.
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 hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious dining area with high ceilings, wicker furniture, and large windows.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
S$471
includes taxes & fees
19 Oct - 20 Oct
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.
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Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"The staff was wonderful from checking in to Charlene at the tiki bar. Beautiful property. We will definitely be back."
Joye 2-night trip
Posted 3 hours ago
Islander Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"This was a lovely hotel in a good location. Rooms were clean the staff was lovely! The only thing I would say was the water pressure wasn’t great and not very hot either. Breakfast was good."
Kristy 3-night trip
Posted 8 hours ago
Fisher Inn Resort & Marina
Drop Anchor

Drop Anchor

10/10 Excellent
"Very clean property. Rooms well maintained and quiet."
Kelly 4-night trip
Posted 2 days ago
Drop Anchor
Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"All good thanks"
Ryan 2-night trip
Posted 3 days ago
Breezy Palms Resort
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Very clean resort. The pool was fabulous. The tiki bar was great. Stall friendly and helpful. Truly enjoyed my stay!"
Maureen 2-night trip
Posted 3 days ago
Amara Cay Resort
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Amazing gym, really cool pool with waterfall, beautiful view of the sunrise on a small beach. Overall was super nice."
Heidi 2-night trip
Posted 5 days ago
Coconut Cove Resort and Marina
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Great place for the money!"
Nicholas 2-night trip
Posted 6 days ago
Hadley Resort and Marina
Casa Morada

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 2 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.

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