Hotel with Pool in Islamorada: Find Hotel with Pool in Islamorada

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

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

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Matecumbe

Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.

HK$1,185

HK$1,774 total

includes taxes & fees

24 Sept - 25 Sept

A tropical resort with a swimming pool, palm trees, and a waterfall.

A balcony with a view of palm trees and the sea, a white railing, and a table with chairs.

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

A bar area with a thatched roof, wooden chairs, and a view of the ocean.

2. Cheeca Lodge & Spa

Matecumbe

Tropical paradise swim experience awaits with three refreshing pools and poolside service.

HK$1,169

HK$1,889 total

includes taxes & fees

24 Sept - 25 Sept

A resort with a pool, beach, and ocean view.

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.

A seaside resort with a glass balustrade, outdoor seating, and a mural of tropical leaves.

3. 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.

HK$1,563

HK$2,332 total

includes taxes & fees

29 Sept - 30 Sept

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

A paved pathway leading to a beach with palm trees and a view of the ocean.

A wooden pier leading to a beach with palm trees and a row of beach huts.

4. Islander Resort

Matecumbe

Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.

HK$1,536

HK$2,257 total

includes taxes & fees

29 Sept - 30 Sept

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 hotel room with a sofa, a small round table, a desk with a chair, and a view of the sea through large windows.

A beach with palm trees, a dock, and lounge chairs.

5. Amara Cay Resort

Matecumbe

Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.

HK$1,213

HK$1,938 total

includes taxes & fees

24 Sept - 25 Sept

A resort with a central swimming pool surrounded by palm trees and a view of the ocean.

A beachside lounge with a wooden deck, thatched roof, and tropical plants.

A bar area with a counter, stools, and potted plants.

6. Bayside Villas by Islander Resort

Matecumbe

Poolside paradise in the heart of Matecumbe beckons with loungers under shady umbrellas.

HK$1,934

HK$2,705 total

includes taxes & fees

23 Sept - 24 Sept

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.

7. Coconut Cove Resort and Marina

Islamorada

Splash into holiday mode at a Florida Keys gem with 24-hour pool access for endless aquatic adventures.

HK$1,169

HK$1,315 total

includes taxes & fees

24 Sept - 25 Sept

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

Islamorada

Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.

HK$860

HK$1,224 total

includes taxes & fees

23 Sept - 24 Sept

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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 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

Matecumbe

HK$1,185

HK$1,774 total

includes taxes & fees

24 Sept - 25 Sept

A coastal resort with a beach, a swimming pool, and multiple buildings.

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

Islamorada

HK$1,563

HK$2,332 total

includes taxes & fees

29 Sept - 30 Sept

Coconut Cove Resort and Marina

Islamorada

HK$1,169

HK$1,315 total

includes taxes & fees

24 Sept - 25 Sept

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.

Fisher Inn Resort & Marina

Islamorada

HK$860

HK$1,224 total

includes taxes & fees

23 Sept - 24 Sept

An aerial view of a resort with a large pool, palm trees, and a beach.

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.

A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

HK$2,063

HK$2,754 total

includes taxes & fees

5 Oct - 6 Oct

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 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

Matecumbe

HK$927

HK$1,299 total

includes taxes & fees

28 Sept - 29 Sept

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 beach bar with a thatched roof, palm trees, and a view of the sea.

A modern hotel room with a large bed, a desk with a lamp, a chair, and a view of the ocean.

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

Key Largo

HK$1,859

HK$2,524 total

includes taxes & fees

1 Oct - 2 Oct

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 bathroom with a white vanity, a mirror, a sink, a cabinet, and a towel rack.

Coconut Palm Inn

Tavernier

HK$1,476

HK$1,969 total

includes taxes & fees

24 Sept - 25 Sept

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.

A hotel room with a bed, a TV, a sofa, and a balcony with a view.

A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

HK$699

HK$1,035 total

includes taxes & fees

29 Sept - 30 Sept

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 hotel room with a large bed, a desk with a television, a chair, a desk lamp, and a window with curtains.

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.

Key Largo Inn

Key Largo

HK$734

HK$826 total

includes taxes & fees

23 Sept - 24 Sept

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Hotels with pools and hot tubs in Islamorada

Coconut Cove Resort and Marina

Islamorada

HK$1,169

HK$1,315 total

includes taxes & fees

24 Sept - 25 Sept

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

Cheeca Lodge & Spa

Matecumbe

HK$1,169

HK$1,889 total

includes taxes & fees

24 Sept - 25 Sept

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

HK$2,063

HK$2,754 total

includes taxes & fees

5 Oct - 6 Oct

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

Matecumbe

HK$3,248

HK$4,151 total

includes taxes & fees

1 Oct - 2 Oct

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

Key Largo

HK$1,859

HK$2,524 total

includes taxes & fees

1 Oct - 2 Oct

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

HK$699

HK$1,035 total

includes taxes & fees

29 Sept - 30 Sept

A pool area with palm trees and a building with a white roof.

A coastal property with a grassy lawn, palm trees, and a white fence overlooking the sea.

A spacious interior with a central open area, a balcony with a railing, and a tiled floor.

A coastal scene with rocky shores, a wooden pier, and calm water.

Bahia Bay Resort

Rock Harbor

HK$1,052

HK$1,184 total

includes taxes & fees

24 Sept - 25 Sept

A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

A 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.

Kona Kai Resort and Gallery - Adults Only

Rock Harbor

HK$994

HK$1,338 total

includes taxes & fees

23 Sept - 24 Sept

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4-star hotels with pools in Islamorada

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

Islamorada

HK$1,563

HK$2,332 total

includes taxes & fees

29 Sept - 30 Sept

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

Matecumbe

HK$1,213

HK$1,938 total

includes taxes & fees

24 Sept - 25 Sept

Islander Resort

Matecumbe

HK$1,536

HK$2,257 total

includes taxes & fees

29 Sept - 30 Sept

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

HK$2,063

HK$2,754 total

includes taxes & fees

5 Oct - 6 Oct

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

Key Largo

HK$1,859

HK$2,524 total

includes taxes & fees

1 Oct - 2 Oct

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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