Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

Top Islamorada Hotels with a Pool

Exterior
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 star property
Long Key
  • 3 outdoor pools
  • Pool loungers
  • On private beach
9.2 out of 10, Wonderful, (1095)
Refreshing pools surrounded by comfortable loungers create an aquatic paradise at this beachfront resort. Kayaking, tennis, and yoga complement the water experience, while Florida Boy restaurant serves delicious meals after sun-drenched adventures.
Lime Tree Bay Resort
Outdoor spa tub
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 star property
Matecumbe
  • 2 outdoor pools
  • Pool loungers
  • On private beach
9.2 out of 10, Wonderful, (1567)
Pool enthusiasts savor 2 pristine outdoor pools surrounded by comfortable loungers, perfect for sunbathing between kayaking excursions. Family-friendly with adult supervision required, this refreshing oasis complements fishing and boating adventures.
The price is ￥21,372
￥32,709 total
includes taxes & fees
Nov 20 - Nov 21
Chesapeake Beach Resort
Aerial view
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham

3.0 star property
Key Largo
  • Outdoor pool
  • Pool loungers
  • Hot tub
7.6 out of 10, Good, (1001)
Crystal waters invite leisurely swims at the sun-drenched outdoor pool, complemented by a soothing hot tub for evening relaxation. Kayaking, bicycling, and fishing adventures await, while sunrise views from balconies showcase spectacular oceanfront panoramas.
The price is ￥16,289
￥23,210 total
includes taxes & fees
Nov 13 - Nov 14
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior detail
Rock Reef Resort

Rock Reef Resort

2.5 star property
Rock Harbor
  • Outdoor pool
  • Pool loungers
  • On private beach
9.2 out of 10, Wonderful, (1056)
Crystal-clear waters invite swimmers to the immaculate heated pool, surrounded by comfortable loungers and shaded umbrellas. Beyond the pool deck, a private beach, kayaking adventures, and wildlife sightings await at this serene waterfront sanctuary.
Rock Reef Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view
Drop Anchor

Drop Anchor

3.0 star property
Islamorada
  • Outdoor pool
  • Pool loungers
  • Near private beach
8.8 out of 10, Excellent, (1001)
Sparkling turquoise waters welcome swimmers to the immaculate outdoor pool, complete with comfortable loungers for sun-drenched relaxation. Beyond the pool deck, guests discover complimentary bicycles, kayaks, and a private beach area with umbrellas.
The price is ￥16,783
￥24,274 total
includes taxes & fees
Nov 16 - Nov 17
Drop Anchor
Superior Bungalow, Multiple Beds, Beachfront (Ground Level Sleeps 6) | View from room
La Jolla Resort

La Jolla Resort

2.5 star property
Matecumbe
  • Outdoor pool
  • Pool loungers
  • On private beach
9.0 out of 10, Wonderful, (1000)
Poolside perfection awaits at this Florida Keys haven, where crystal waters complement the private beach experience. Guests relax on sun loungers after kayaking adventures, then witness spectacular sunsets from this serene waterfront sanctuary.
La Jolla Resort
Outdoor pool
Treasure Harbor

Treasure Harbor

3.0 star property
Islamorada
  • Outdoor pool
9.0 out of 10, Wonderful, (109)
Treasure Harbor
Outdoor pool, open 8:00 AM to 11:00 PM, sun loungers
Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo

3.5 star property
Tavernier
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • On private beach
8.4 out of 10, Very Good, (1009)
Sparkling waters beckon from the outdoor pool, surrounded by comfortable loungers for soaking up the Florida sun. After swimming, guests savor oceanfront dining at the Island Grill Restaurant or sip refreshing drinks at the poolside bar.
The price is ￥19,883
￥25,141 total
includes taxes & fees
Nov 19 - Nov 20
Ocean Pointe Suites at Key Largo
Exterior
Breezy Palms Resort

Breezy Palms Resort

2.5 star property
Matecumbe
  • Outdoor pool
  • Pool loungers
  • On the beach
8.8 out of 10, Excellent, (562)
Floating in the refreshing pool while loungers beckon sunbathers creates the perfect complement to oceanfront adventures. Guests appreciate the clean facilities, peaceful atmosphere, and proximity to fishing spots at this waterfront haven.
The price is ￥10,662
￥19,982 total
includes taxes & fees
Nov 16 - Nov 17
Breezy Palms Resort
Terrace/patio
Bayside Inn Key Largo

Bayside Inn Key Largo

3.0 star property
Key Largo
  • Outdoor pool
  • On private beach
8.6 out of 10, Excellent, (1601)
Splashing into vacation mode becomes effortless at this waterfront haven with a private beach and outdoor pool. Kayaks, bicycles, and fishing opportunities invite adventure while the tranquil pool deck serves as front-row seating to breathtaking sunset panoramas.
The price is ￥19,874
￥26,210 total
includes taxes & fees
Nov 20 - Nov 21
Bayside Inn Key Largo
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Our room was beautiful and spotless. The staff was always polite, handling any inquiry or request. The location is ideal, located on the beach with easy access to the main road. They provide a nice breakfast from 6 to 10 every morning with a variety of options to choose from on top of 24-hour coffee."
Cheryl 3-night trip
Posted 3 days ago
Chesapeake Beach Resort

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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 111 places to stay with pools. During your trip, you can explore sights such as Bud n' Mary's Dive Center and Islamorada County Park, 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. Bayside Villas by Islander Resort: Provides 3 restaurants, an outdoor pool, and free self parking. Drop Anchor: Features free self parking, an outdoor pool, and complimentary bicycles. Sands of Islamorada: Offers free self parking, a pool, and complimentary wireless internet access.
How many pool hotels should I expect to find in Islamorada?
Expedia's 111 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Spend some time experiencing the great outdoors at Islamorada County Park and Anne's Beach. Discover sights such as Bud n' Mary's Dive Center, Fiesta Key, and Everglades National Park 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.