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

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$246 nightly
The price is $276 total per night
$276 total
Sep 21 - Sep 22
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.
On private beach
Pool

Islander Resort
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$256 nightly
The price is $287 total per night
$287 total
Sep 22 - Sep 23
Total with taxes and fees
Guests of Islander Resort have access to a private beach, 2 outdoor pools, and a gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, luggage storage, and dry cleaning/laundry. Other amenities at this beach hotel include free WiFi in public areas, meeting rooms, and a conference center.
On private beach
Pool

La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$223 nightly
The price is $251 total per night
$251 total
Sep 24 - Sep 25
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. 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.
On private beach
Pool

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $179 total per night
$179 total
Sep 24 - Sep 25
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 concierge services, securing valuables, and dry cleaning/laundry. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool

Drop Anchor
84959 Overseas Highway, 222, Islamorada, FL
$143 nightly
The price is $157 total per night
$157 total
Sep 28 - Sep 29
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 a picnic area.
Pool
Pet friendly

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$220 nightly
The price is $247 total per night
$247 total
Oct 1 - Oct 2
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.
On private beach
Pool

Pines & Palms Resort
80401 Old Hwy, Islamorada, FL
$178 nightly
The price is $200 total per night
$200 total
Sep 24 - Sep 25
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.
On private beach
Pool

Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $146 total per night
$146 total
Sep 25 - Sep 26
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 concierge services and luggage storage. 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.
On private beach
Pool

Bayside Villas by Islander Resort
81450 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$257 nightly
The price is $289 total per night
$289 total
Sep 28 - Sep 29
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 barbecue grills and a picnic area.
Pool
Pet friendly

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
$149 nightly
The price is $168 total per night
$168 total
Sep 21 - Sep 22
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.
Pool
Breakfast included

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.
Pool
Hot Tub

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$173 nightly
The price is $194 total per night
$194 total
Sep 23 - Sep 24
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.
On private beach
Pool

Casa Morada
136 Madeira Road, Islamorada, FL
$242 nightly
The price is $272 total per night
$272 total
Sep 24 - Sep 25
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, securing valuables, 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 adults-only hotel include free newspapers, a terrace, and laundry facilities.
Pool
Breakfast included

Sands of Islamorada
80051 Overseas Highway, Islamorada, FL
$173 nightly
The price is $195 total per night
$195 total
Sep 21 - Sep 22
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 garden, and barbecue grills.
Pool
Pet friendly

Breezy Palms Resort
80015 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$133 nightly
The price is $148 total per night
$148 total
Oct 1 - Oct 2
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 gift shop.
Pool
Kitchen
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 | 2,206 hotels |
---|---|
Lowest Price | $146 |
Highest Price | $289 |
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

Cheeca Lodge & Spa
5/5 Excellent
"Exceptional customer service, a plethora of activities and in a central location with many desirable businesses within a close reach."
A verified traveler stayed at Cheeca Lodge & Spa
Posted 3 days ago
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