Islamorada Hotels with Swimming Pool

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Check availability on Islamorada Hotels with Swimming Pools

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Islamorada Hotels with Swimming Pools

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, (1075)
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.
The price is RM373
RM419 total
includes taxes & fees
1 Dec - 2 Dec
Rock Reef 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 RM382
RM561 total
includes taxes & fees
7 Dec - 8 Dec
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 star property
Islamorada
  • Outdoor pool
  • Pool loungers
  • On private beach
8.2 out of 10, Very good, (1017)
Paddle into adventure with free kayaks, bikes, and fishing opportunities steps from the heated outdoor pool. Surrounded by ocean views, this art deco retreat offers pristine beaches with sun loungers and spectacular sunrise panoramas.
The price is RM346
RM524 total
includes taxes & fees
18 Dec - 19 Dec
Fisher Inn Resort & Marina
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, (1590)
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 RM517
RM814 total
includes taxes & fees
3 Dec - 4 Dec
Chesapeake Beach Resort
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, (1005)
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.
The price is RM315
RM470 total
includes taxes & fees
2 Dec - 3 Dec
La Jolla Resort
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, (1113)
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
Fishing
Creekside Inn

Creekside Inn

2.5 star property
Tavernier
  • 2 outdoor pools
  • Pool loungers
  • Near the beach
8.0 out of 10, Very good, (1009)
Surrounded by serene canal views, both pools offer perfect vantage points for stunning sunsets after days spent boating or fishing. Comfortable loungers and shade umbrellas complement this waterfront retreat where ocean adventures begin and end.
The price is RM517
RM582 total
includes taxes & fees
1 Dec - 2 Dec
Creekside Inn
Water view
Drop Anchor

Drop Anchor

3.0 star property
Islamorada
  • Outdoor pool
  • Pool loungers
  • Near private beach
8.8 out of 10, Excellent, (1004)
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 RM345
RM533 total
includes taxes & fees
30 Nov - 1 Dec
Drop Anchor
Outdoor pool
Treasure Harbor

Treasure Harbor

3.0 star property
Islamorada
  • Outdoor pool
9.0 out of 10, Wonderful, (114)
Treasure Harbor
Exterior
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3.0 star property
Islamorada
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (142)
Sparkling waters beckon at the 24-hour accessible pool, surrounded by sun loungers perfect for basking after kayaking adventures. Children splash in their own dedicated pool while adults appreciate the clean, serene atmosphere near the beach.
The price is RM554
RM623 total
includes taxes & fees
1 Dec - 2 Dec
Coconut Cove Resort and Marina
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David were our poolside attendants, and Jessica at the front desk was very helpful. "
Callie 4-night trip
Posted 2 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 136 places to stay with pools. During your visit, you can explore sights such as Everglades National Park and Florida Keys Brewing Co., 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. Bayside Villas by Islander Resort: Offers 3 restaurants, an outdoor pool and free self parking. Fisher Inn Resort & Marina: Provides a private beach, a pool and daily. 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 136 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Explore places such as Everglades National Park while you're in Islamorada. Enjoy a stroll along the shore at Anne's Beach and Sunset Drive Beach. 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.