Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

Compare Islamorada Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1236)
"Really quiet spot in the beautiful Florida Keys. Food was amazing and wonderful service. "
The price is SAR 1,038
SAR 1,417 total
includes taxes & fees
4 May - 5 May
Amara Cay Resort
Islander Resort
Exterior

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1024)
"Great hotel, lovely staff. Rooms a little tired now, but overall a great experience. "
The price is SAR 927
SAR 1,280 total
includes taxes & fees
27 Apr - 28 Apr
Islander Resort
La Siesta Resort & Villas
Outdoor pool, sun loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1021)
"This is a beautiful resort ! Lots of dining choices around although just room service on property. There is also no liquor drinks at their tiki pool bar . They have wine and spritzers and ice cream. Very family friendly!!! Views were amazing and staff were super friendly and accommodating! Has room service "
The price is SAR 898
SAR 1,259 total
includes taxes & fees
4 May - 5 May
La Siesta Resort & Villas
Cheeca Lodge & Spa
Private beach, sun loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1063)
"High end 5 star relaxation"
The price is SAR 1,017
SAR 1,398 total
includes taxes & fees
27 Apr - 28 Apr
Cheeca Lodge & Spa
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1010)
"On the third night of our 3-night stay and wishing we could stay forever! We splurged on a direct ocean front room and it is worth every penny. This place is by no means fancy but it is old Florida at its finest: cozy, chill, unpretentious. Add in a heated pool and a drip (not pod!!) coffeemaker and all boxes have been checked. As with most of the upper keys there is no true walkout sandy beach but you can use the kayak ramp to get in an ocean swim. Note mucky bottom so mann up or wear swim...
The price is SAR 1,117
SAR 1,388 total
includes taxes & fees
9 Apr - 10 Apr
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3 outdoor pools, a heated pool, pool umbrellas, sun loungers

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

3.5 star property
8.0 out of 10, Very Good, (1012)
"Beautiful place and Staff was attentive."
The price is SAR 1,432
SAR 1,860 total
includes taxes & fees
27 Apr - 28 Apr
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort
Outdoor pool, a heated pool, pool umbrellas, sun loungers

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (983)
"Absolutely perfect! We stayed in the 3 bedroom villa. Tremendous space and beautiful views of the ocean. All of the fun was literally outside our front door. It was very hard to leave. Highly recommended this place! "
The price is SAR 1,047
SAR 1,384 total
includes taxes & fees
7 Apr - 8 Apr
Pines & Palms Resort
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
7.8 out of 10, Good, (1020)
"Was a lovely fresh clean large room!"
The price is SAR 790
SAR 1,011 total
includes taxes & fees
6 Apr - 7 Apr
Fisher Inn Resort & Marina
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (360)
"It was ok I suppose. Not really worth the money. "
The price is SAR 1,197
SAR 1,583 total
includes taxes & fees
27 Apr - 28 Apr
Islander Bayside Villas and Boatslips
Coconut Cove Resort and Marina
Outdoor pool, sun loungers

Coconut Cove Resort and Marina

2.5 star property
7.6 out of 10, Good, (749)
"Great location. Great pool. Water view. Nice rooms."
The price is SAR 671
SAR 755 total
includes taxes & fees
6 Apr - 7 Apr
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.
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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 21 places to stay with pools. During your trip, you can explore sights such as Everglades National Park and Florida Keys Brewing Co., 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 sun loungers. Fisher Inn Resort & Marina: Offers a private beach, a pool, and daily. Drop Anchor: Provides free self parking, an outdoor pool, and complimentary bicycles. Sands of Islamorada: Features free self parking, a pool, and complimentary wireless internet access. Islander Bayside Villas and Boatslips: Offers free self parking, an outdoor pool, and complimentary wireless internet access.
How many pool hotels should I expect to find in Islamorada?
Expedia’s 21 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Explore places like 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 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.