Hotels with a Pool in Islamorada, FL
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Featured Islamorada Hotels with Pool

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$309 nightly
The price is $348 total per night
$348 total
Feb 8 - Feb 9
Total with taxes and fees
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a meeting room, a terrace, and laundry facilities.

Islander Resort
82100 Overseas Highway Islamorada FL
$450 nightly
The price is $506 total per night
$506 total
Feb 9 - Feb 10
Total with taxes and fees
Guests of Islander Resort have access to a private beach, 2 outdoor pools, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, luggage storage, and concierge services. Other amenities at this beach hotel include free WiFi in public areas, meeting rooms, and a conference center.

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$409 nightly
The price is $460 total per night
$460 total
Feb 10 - Feb 11
Total with taxes and fees
Guests of La Siesta Resort & Villas have access to a private beach, a marina, and an outdoor pool. Transportation is made easy with a free area shuttle. The 24-hour front desk has staff always at the ready. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a terrace, wedding services, and a picnic area.

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$448 nightly
The price is $505 total per night
$505 total
Feb 10 - Feb 11
Total with taxes and fees
Cheeca Lodge & Spa features a private beach, a golf course, and a full-service spa. Free valet and self parking are available, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and concierge services. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$379 nightly
The price is $422 total per night
$422 total
Feb 7 - Feb 8
Total with taxes and fees
Guests of Drop Anchor enjoy an outdoor pool, free WiFi in public areas, and a business center. If you drive, put free parking to good use. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include coffee/tea in a common area, free use of bicycles, and barbecue grills.

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$526 nightly
The price is $591 total per night
$591 total
Feb 16 - Feb 17
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort features a private beach, a marina, and 3 outdoor pools. Transportation is made easy with a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, free WiFi in public areas, and meeting rooms.

Pines & Palms Resort
80401 Old Hwy Islamorada FL
$518 nightly
The price is $583 total per night
$583 total
Feb 9 - Feb 10
Total with taxes and fees
Guests of Pines & Palms Resort have access to a private beach, a marina, and an outdoor pool. You can take advantage of free parking, along with limo/town car service. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and a terrace.

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$239 nightly
The price is $269 total per night
$269 total
Feb 11 - Feb 12
Total with taxes and fees
Guests staying at Fisher Inn Resort & Marina enjoy access to a private beach, an outdoor pool, and free WiFi in public areas. Free parking is available if you drive. Front-desk staff can assist with luggage storage and concierge services. Other amenities at this beach motel include coffee/tea in a common area, a microwave in a common area, and a refrigerator in a common area.

Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
$411 nightly
The price is $462 total per night
$462 total
Feb 10 - Feb 11
Total with taxes and fees
Guests of Bayside Villas by Islander Resort enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. There's free parking and a free area shuttle. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this beach hotel include a picnic area and barbecue grills.

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$282 nightly
The price is $318 total per night
$318 total
Feb 8 - Feb 9
Total with taxes and fees
Guests of Coconut Cove Resort and Marina enjoy a marina, an outdoor pool, and a children's pool. If you plan to drive, free parking is available. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Other amenities at this beach hotel include a gym, free WiFi in public areas, and a business center.

The Caribbean Resort
117 Carroll St Islamorada FL
Guests staying at The Caribbean Resort enjoy access to a marina, an outdoor pool, and a hot tub. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this family-friendly hotel include free use of bicycles, a terrace, and laundry facilities.

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$373 nightly
The price is $420 total per night
$420 total
Feb 11 - Feb 12
Total with taxes and fees
Chesapeake Beach Resort features a private beach, a marina, and 2 outdoor pools. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and free use of bicycles.

Casa Morada
136 Madeira Road Islamorada FL
$412 nightly
The price is $464 total per night
$464 total
Feb 11 - Feb 12
Total with taxes and fees
Guests of Casa Morada enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. There's free parking if you drive. Front-desk staff can assist with tours or tickets, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this adults-only hotel include free newspapers, a terrace, and laundry facilities.

Sands of Islamorada
80051 Overseas Highway Islamorada FL
$208 nightly
The price is $234 total per night
$234 total
Mar 8 - Mar 9
Total with taxes and fees
Guests of Sands of Islamorada enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. If you drive, put free parking to good use. Front-desk staff can help secure valuables, and provide local restaurant recommendations. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include laundry facilities, a picnic area, and barbecue grills.

Breezy Palms Resort
80015 Overseas Highway Islamorada FL
$251 nightly
The price is $283 total per night
$283 total
Feb 7 - Feb 8
Total with taxes and fees
Guests staying at Breezy Palms Resort enjoy access to a marina, an outdoor pool, and free WiFi in public areas. Self parking is available for USD 30.00 per day. Helpful staff can provide tour or ticket assistance, luggage storage, and a safe deposit box at the front desk. Other amenities at this beach aparthotel include a terrace, laundry facilities, and a picnic area.
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.
Islamorada hotels essential information
Accommodation | 2,114 hotels |
|---|---|
Lowest Price | $234 |
Highest Price | $591 |
Popular hotels | Amara Cay Resort, Islander Resort, La Siesta Resort & Villas, Cheeca Lodge & Spa, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Pines & Palms Resort, Fisher Inn Resort & Marina, Bayside Villas by Islander Resort, Coconut Cove Resort and Marina, The Caribbean Resort, Chesapeake Beach Resort, Casa Morada, Sands of Islamorada, Breezy Palms Resort |
Recent Hotels with Pool Reviews

Chesapeake Beach Resort
5/5 Excellent
"We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had. "
A verified traveler stayed at Chesapeake Beach Resort
Posted 2 days ago
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