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

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Check availability on Islamorada Hotels with a Pool

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Islamorada hotels with a pool

2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
Private beach, white sand, sun loungers, beach towels
Hypo-allergenic bedding available, pillowtop beds, laptop workspace
Deluxe Ocean View Two Queen Suite | Balcony

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
￥22,512
￥34,150 total
includes taxes & fees
Sep 28 - Sep 29
Chesapeake Beach Resort
Property grounds
Poolside bar
Beach/ocean view
Premium bedding, in-room safe, desk, laptop workspace

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
￥21,739
￥35,930 total
includes taxes & fees
Sep 24 - Sep 25
Cheeca Lodge & Spa
View from property
Room, 1 King Bed, Balcony, Ocean View (Balcony) | Premium bedding, in-room safe, laptop workspace, iron/ironing board
Exterior
View from property

3. 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.
￥31,250
￥46,630 total
includes taxes & fees
Sep 28 - Sep 29
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior
View from room
Dock
3 restaurants; breakfast, lunch, dinner, and brunch served

4. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
￥30,360
￥44,744 total
includes taxes & fees
Sep 30 - Oct 1
Islander Resort
Outdoor pool, pool umbrellas, sun loungers
View from room
View from room
Room, 1 King Bed with Sofa bed, Standard Partial Ocean View | View from room

5. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
￥22,553
￥36,845 total
includes taxes & fees
Sep 24 - Sep 25
Amara Cay Resort
Exterior
Brand New Two King Bedroom Bay View | Premium bedding, pillowtop beds, in-room safe, blackout drapes
Dock
Bar (on property)

6. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
  • Poolside paradise in the heart of Matecumbe beckons with loungers under shady umbrellas.
￥38,777
￥54,241 total
includes taxes & fees
Sep 23 - Sep 24
Bayside Villas by Islander Resort
Exterior
Exterior
Exterior
Front of property

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.
￥22,674
￥25,508 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
Outdoor pool, open 7:00 AM to 7:00 PM, pool umbrellas, sun loungers
Oceanview Seaside Villa | Premium bedding, blackout drapes, iron/ironing board, cribs (free)
Beach/ocean view
Exterior

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.
￥17,249
￥24,538 total
includes taxes & fees
Sep 23 - Sep 24
Fisher Inn Resort & Marina
View from property
Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio
Waterfront Studio with King Bed & Kitchenette | Premium bedding, minibar, in-room safe, desk
Waterfront Bougainvillea Two-Bedroom Master Suite | Private kitchen | Coffee/tea maker, fridge, microwave

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.
￥16,832
￥25,996 total
includes taxes & fees
Sep 24 - Sep 25
Lime Tree Bay Resort
Aerial view
Aerial view
Oceanfront Three Bedroom Villa | Premium bedding, iron/ironing board, WiFi (free), individually decorated
Oceanfront Three Bedroom Villa | Premium bedding, iron/ironing board, WiFi (free), individually decorated

10. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
￥18,405
￥29,379 total
includes taxes & fees
Sep 24 - Sep 25
Pines & Palms Resort
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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

Private beach, white sand, sun loungers, beach towels
Deluxe Ocean View Two Queen Suite | Balcony
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
Water view

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
￥22,512
￥34,150 total
includes taxes & fees
Sep 28 - Sep 29
Chesapeake Beach Resort
Room, 1 King Bed, Balcony, Ocean View (Balcony) | Premium bedding, in-room safe, laptop workspace, iron/ironing board
Private beach, sun loungers, beach towels, scuba diving
View from property
Banquet hall

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
￥31,250
￥46,630 total
includes taxes & fees
Sep 28 - Sep 29
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior
Exterior
Exterior
Front of property

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
￥22,674
￥25,508 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
Exterior
Dock
Outdoor pool, open 7:00 AM to 7:00 PM, pool umbrellas, sun loungers
Beach/ocean view

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
￥17,249
￥24,538 total
includes taxes & fees
Sep 23 - Sep 24
Fisher Inn Resort & Marina
Exterior
Outdoor pool, cabanas (surcharge), pool umbrellas
3 restaurants; breakfast, lunch, dinner, and brunch served
Beach House, 3 Bedrooms, Pool Access, Bay View (Balcony/Patio, Private Pool) | Beach | On the beach, beach cabanas, sun loungers, beach umbrellas

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
￥41,259
￥55,065 total
includes taxes & fees
Oct 5 - Oct 6
Playa Largo Resort & Spa, Autograph Collection
Balcony view
Exterior detail
Private beach, sun loungers, beach towels, kayaking
Dock

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
￥18,586
￥26,042 total
includes taxes & fees
Sep 28 - Sep 29
Hadley Resort and Marina
2 restaurants; breakfast, lunch, and dinner served
2 outdoor pools, pool umbrellas, sun loungers
Exterior
Premium bedding, pillowtop beds, in-room safe, desk

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
￥37,177
￥50,473 total
includes taxes & fees
Oct 1 - Oct 2
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Private beach, white sand, sun loungers, beach umbrellas
Premium Room, Partial Sea-View | Premium bedding, pillowtop beds, laptop workspace
Outdoor pool, pool umbrellas, sun loungers
Shower, designer toiletries, hair dryer, towels

Coconut Palm Inn

Coconut Palm Inn
Tavernier
￥29,509
￥39,376 total
includes taxes & fees
Sep 24 - Sep 25
Coconut Palm Inn
Exterior
Premium bedding, pillowtop beds, in-room safe, desk
Exterior
Coffee/tea maker

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
￥14,016
￥20,756 total
includes taxes & fees
Sep 29 - Sep 30
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior
Exterior
King, Non Smoking | Blackout drapes, WiFi (free), bed sheets
Restaurant

Key Largo Inn

Key Largo Inn
Key Largo
￥14,097
￥15,859 total
includes taxes & fees
Sep 28 - Sep 29
Key Largo Inn
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Hotels with pools and hot tubs in Islamorada

Exterior
Exterior
Exterior
Front of property

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
￥22,674
￥25,508 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
Balcony
Premium bedding, in-room safe, desk, laptop workspace
Poolside bar
Lobby

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
￥21,739
￥35,930 total
includes taxes & fees
Sep 24 - Sep 25
Cheeca Lodge & Spa
Exterior
Outdoor pool, cabanas (surcharge), pool umbrellas
3 restaurants; breakfast, lunch, dinner, and brunch served
Beach House, 3 Bedrooms, Pool Access, Bay View (Balcony/Patio, Private Pool) | Beach | On the beach, beach cabanas, sun loungers, beach umbrellas

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
￥41,259
￥55,065 total
includes taxes & fees
Oct 5 - Oct 6
Playa Largo Resort & Spa, Autograph Collection
Daily cooked-to-order breakfast for a fee
Property grounds
Property entrance
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
￥64,948
￥83,014 total
includes taxes & fees
Oct 1 - Oct 2
The Islands of Islamorada
2 restaurants; breakfast, lunch, and dinner served
2 outdoor pools, pool umbrellas, sun loungers
Exterior
Premium bedding, pillowtop beds, in-room safe, desk

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
￥37,177
￥50,473 total
includes taxes & fees
Oct 1 - Oct 2
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Exterior
Premium bedding, pillowtop beds, in-room safe, desk
Exterior
Coffee/tea maker

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
￥14,016
￥20,756 total
includes taxes & fees
Sep 29 - Sep 30
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Terrace/patio
Interior entrance
BBQ/picnic area
Balcony

Bahia Bay Resort

Bahia Bay Resort
Rock Harbor
￥19,407
￥21,833 total
includes taxes & fees
Oct 1 - Oct 2
Bahia Bay Resort
Breadfruit Suite | Terrace/patio
Exterior
Exterior
Exterior

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
￥19,923
￥26,838 total
includes taxes & fees
Sep 24 - Sep 25
Kona Kai Resort and Gallery - Adults Only
View all properties

4-star hotels with pools in Islamorada

Room, 1 King Bed, Balcony, Ocean View (Balcony) | Premium bedding, in-room safe, laptop workspace, iron/ironing board
Private beach, sun loungers, beach towels, scuba diving
View from property
Banquet hall

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
￥31,250
￥46,630 total
includes taxes & fees
Sep 28 - Sep 29
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
View from room
Outdoor pool, pool umbrellas, sun loungers
View from room
Aerial view

Amara Cay Resort

Amara Cay Resort
Matecumbe
￥22,553
￥36,845 total
includes taxes & fees
Sep 24 - Sep 25
Amara Cay Resort
Exterior
View from room
Dock
3 restaurants; breakfast, lunch, dinner, and brunch served

Islander Resort

Islander Resort
Matecumbe
￥30,360
￥44,744 total
includes taxes & fees
Sep 30 - Oct 1
Islander Resort
Exterior
Outdoor pool, cabanas (surcharge), pool umbrellas
3 restaurants; breakfast, lunch, dinner, and brunch served
Beach House, 3 Bedrooms, Pool Access, Bay View (Balcony/Patio, Private Pool) | Beach | On the beach, beach cabanas, sun loungers, beach umbrellas

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
￥41,259
￥55,065 total
includes taxes & fees
Oct 5 - Oct 6
Playa Largo Resort & Spa, Autograph Collection
2 restaurants; breakfast, lunch, and dinner served
2 outdoor pools, pool umbrellas, sun loungers
Exterior
Premium bedding, pillowtop beds, in-room safe, desk

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
￥37,177
￥50,473 total
includes taxes & fees
Oct 1 - Oct 2
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

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"Very quiet and peaceful stay. Amazing water and beach views from the balcony."
Michelle 4-night trip
Posted 6 hours ago
Chesapeake Beach Resort
La Jolla Resort

La Jolla Resort

10/10 Excellent
"Beautiful and quaint property located on the Gulf side with water access. Clean rooms, bathroom is smaller. Centrally located in Islamorada with plenty to do."
James 1-night trip
Posted 15 hours ago
La Jolla Resort
Islander Resort

Islander Resort

10/10 Excellent
"Nice pool"
Henry 1-night trip
Posted 15 hours ago
Islander Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Si quieres unas vacaciones increíbles , este es el lugar"
Yerisleidys 2-night trip
Posted 2 days ago
Hadley Resort and Marina
Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"It was very cozy. I was able to relax while I was celebrating my anniversary with my wife. The bed was super comfortable. The shower was excellent, and the staff was very friendly."
Dionisio 1-night trip
Posted 2 days ago
Breezy Palms Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Clean and comfortable rooms. I love the location relative to things to do in the Keys. We used the bikes while there and have used kayak/paddleboards in past. The staff is absolutely amazing. I had messed up the dates of the reservation. Jamal worked really hard to get me a room at a rate i could afford. REALLY appreciate his efforts. We'll stay here again on our next trip to Islamorada"
Scott 6-night trip
Posted 3 days ago
Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Excellent stay! Love this place and will definitely be back!"
Hailey Ritch and Patrick 3-night trip
Posted 4 days ago
Coconut Cove Resort and Marina
Drop Anchor

Drop Anchor

10/10 Excellent
"Great resort. Staff were helpful and the location is amazing"
Heather 1-night trip
Posted 7 days ago
Drop Anchor

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.

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