Hotels with a Pool in Islamorada, FL
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Islamorada Hotels with Pool

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. Transportation is made easy with a free area shuttle. 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 WiFi in public areas, a meeting room, and a terrace.
On private beach
Pool

Islander Resort
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
Islander Resort features a private beach, a golf course, and 2 outdoor pools. Free parking is available if you drive. The front desk has multilingual staff standing by 24 hours a day to assist with luggage storage and tours/tickets. Other amenities at this beach hotel include a gym, free WiFi in public areas, and meeting rooms.
On private beach
Pool

La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
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 WiFi in public areas, a terrace, and a water dispenser.
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
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 dry cleaning/laundry, securing valuables, and tours or tickets. 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
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.
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
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
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
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.
On private beach
Pool

Islander Bayside Villas and Boatslips
81450 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
Guests of Islander Bayside Villas and Boatslips 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. Other amenities at this beach hotel include a picnic area and barbecue grills.
Pool
Pet friendly

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
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
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
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 luggage storage, concierge services, and dry cleaning/laundry. 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
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.
Pool
Pet friendly
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 | 2,199 hotels |
---|---|
Lowest Price | |
Highest Price | |
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, Islander Bayside Villas and Boatslips, Coconut Cove Resort and Marina, The Caribbean Resort, Chesapeake Beach Resort, Casa Morada, Sands of Islamorada, RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES! |
Recent Hotels with Pool Reviews

Chesapeake Beach Resort
5/5 Excellent
"Dog poop in pool area
Found hair in a lot of the towels used
Staff were friendly and dependable "
A verified traveler stayed at Chesapeake Beach Resort
Posted 1 day ago
Other Hotels with Pool
Areas Of Islamorada
Hotels Near
Hotel Themes
Flights To
Top Trending
Hotels
Hotels in Daytona BeachHotels in NaplesBeach Resorts & Hotels in St. AugustineCheap Hotels in Daytona BeachBeach Resorts & Hotels in DestinBeach Resorts & Hotels in SarasotaHotels in Cocoa BeachHotels in Fort MyersHotels in SarasotaCheap Hotels in PensacolaHotels in Fort Walton BeachHotels in Key WestHotels in Fort Myers BeachHotels in St. AugustineHotels in Panama City BeachBeach Resorts & Hotels in PensacolaCheap Hotels in Key WestAll Inclusive Resorts & Hotels in Key WestOceanfront Hotels in Naples
Flights