Book resorts with pools in Islamorada

Experience the Ultimate Family Getaway at Resorts with Pools in Islamorada

Resorts with pools in Islamorada provide the perfect backdrop for a memorable family vacation. Nestled in the picturesque Florida Keys, these resorts offer a blend of relaxation and adventure, making them an ideal choice for families looking to escape the hustle and bustle of everyday life. With the soothing sounds of the ocean and lush tropical landscapes, your family can enjoy quality time together while splashing in the pool or lounging by the water. These properties often feature a variety of amenities designed to entertain and engage guests of all ages, ensuring a fantastic experience for everyone.

Our top choices for a great stay

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
$219 nightly
The price is $247 total per night from Jul 7 to Jul 8
$247 total
Jul 7 - Jul 8
Total includes taxes and fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Matecumbe United Methodist Church and Florida Keys Brewing Co. are located nearby.
9/10 Wonderful! (1,115 reviews)
Cheeca Lodge & Spa
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

3.5 out of 5
$339 nightly
The price is $381 total per night from Jul 7 to Jul 8
$381 total
Jul 7 - Jul 8
Total includes taxes and fees
Stay at this 3.5-star beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and History of Diving Museum are located nearby.
9/10 Wonderful! (41 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
$238 nightly
The price is $268 total per night from Jul 6 to Jul 7
$268 total
Jul 6 - Jul 7
Total includes taxes and fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
8.8/10 Excellent! (1,219 reviews)
Amara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
$233 nightly
The price is $263 total per night from Jul 6 to Jul 7
$263 total
Jul 6 - Jul 7
Total includes taxes and fees
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
8.6/10 Excellent! (1,002 reviews)
La Siesta Resort & Villas
Matecumbe Resort

Matecumbe Resort

2 out of 5
$165 nightly
The price is $186 total per night from Jul 1 to Jul 2
$186 total
Jul 1 - Jul 2
Total includes taxes and fees
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, free parking, and a private beach. Popular attractions Robbie’s of Islamorada and Indian Key Historic State Park are located nearby.
8.8/10 Excellent! (58 reviews)
Matecumbe Resort
Keys Villa

Keys Villa

Stay at this resort in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby.
10/10 Exceptional! (6 reviews)
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Keys Villa
Beautiful oceanfront resort located at mile marker 73.8

Beautiful oceanfront resort located at mile marker 73.8

Stay at this resort in Islamorada. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.
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Beautiful oceanfront resort located at mile marker 73.8
JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub

JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub

Stay at this resort in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby.
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JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub
On the water in Islamorada elevated detached unit!!!

On the water in Islamorada elevated detached unit!!!

Stay at this resort in Islamorada. Enjoy cable/satellite TV service, air conditioning, and an outdoor pool. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby.
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On the water in Islamorada elevated detached unit!!!
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

Stay at this resort in Islamorada. Enjoy laundry facilities, patios, and air conditioning. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby.
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2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
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.

Why choose family resorts with pools in Islamorada over hotels?

Opting for family resorts with pools in Islamorada can elevate your vacation experience beyond what traditional hotels offer. While hotels may provide basic accommodations, these resorts feature expansive outdoor spaces and exciting water features designed for family enjoyment. Picture your family bonding over poolside adventures, where kids can play freely, and parents can unwind in a serene atmosphere. The added amenities at these vacation resorts often include organized activities, family-friendly dining options, and direct beach access, all tailored to enhance your stay. With the opportunity to create lasting memories in a vibrant setting, choosing a resort with a pool is a fantastic way to enjoy both relaxation and exploration during your family retreat.