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Check availability on Islamorada Hotels with Pool

Top Islamorada Hotels with 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, (1092)
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, (1565)
Pool enthusiasts savour 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 Rp2.357.374
Rp3.588.770 total
includes taxes & fees
17 Nov - 18 Nov
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, (1005)
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 Rp1.819.210
Rp2.575.935 total
includes taxes & fees
13 Nov - 14 Nov
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, (1055)
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, (1000)
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 Rp1.256.787
Rp1.998.036 total
includes taxes & fees
13 Nov - 14 Nov
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, (1004)
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, pool 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, (1006)
Sparkling waters beckon from the outdoor pool, surrounded by comfortable loungers for soaking up the Florida sun. After swimming, guests savour oceanfront dining at the Island Grill Restaurant or sip refreshing drinks at the poolside bar.
The price is Rp2.262.446
Rp2.845.023 total
includes taxes & fees
18 Nov - 19 Nov
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 Rp1.155.115
Rp1.898.654 total
includes taxes & fees
18 Nov - 19 Nov
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, (1607)
Splashing into holiday 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 Rp2.148.366
Rp2.833.262 total
includes taxes & fees
30 Nov - 1 Dec
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"It was absolutely beautiful and the staff was always super nice!"
Mary 5-night trip
Posted 3 days ago
Cheeca Lodge & Spa

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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 111 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. 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 will I be able 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 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.