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The Best Hotels for a Weekend Getaway in Islamorada

Islamorada, Florida Islamorada, Florida

If you're planning a weekend getaway to Islamorada, Florida, you'll need to find a great hotel to stay at. We've analyzed all of the hotels in the area based on key criteria to help you figure out where to stay for a weekend in Islamorada. Whether you're a family or a couple, there are plenty of hotels in the area to suit your needs for the perfect long weekend. From affordable rates to luxurious amenities, there's something for everyone. Many of the hotels offer comfortable, relaxing rooms with easy access to nearby activities which are perfect for a 2-day or 3-day trip to the area. You'll also find plenty of great restaurants and bars in the area, perfect for a night out and the ultimate weekend of culture and cuisine. And there's no shortage of things to do in Islamorada, from sightseeing to exploring. So why wait? Book your hotel for a weekend escape in Islamorada at one of these terrific places to start planning your perfect weekend getaway.

(Prices are listed in U.S. Dollars.)

Cheeca Lodge & Spa

4-star Resort with prices starting at $258 (before taxes) - See All Prices
A Great Stay for a Weekend Trip to Islamorada
  • Great Value: the price is lower than average for weekend trip hotels.
  • Beach
  • Family-Friendly
  • Outdoor pool
  • Spa
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Located at 81801 Overseas Highway, Mile Marker 82, Cheeca Lodge & Spa has great rooms from $258 (before taxes). It offers an outdoor pool, room service, a restaurant, a fitness center, and scuba diving. It has a terrific 8.40 rating out of 10 from previous guests who have stayed here. Only 0.7 miles from the city center, visitors will especially love snorkeling, a bar, child care, laundry services, and golf at this convenient hotel. You'll love relaxing in the hot tub at the end of the day, too. The price of this hotel is less than average for weekend trip hotels, which makes it a great value.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Snorkeling
  • Hot tub
  • Spa
  • Beach
  • Family-Friendly
  • Golf
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Babysitting / Child Care
  • Laundry service
  • Game room
  • Free parking
  • Table tennis
  • Fishing
  • Family rooms
  • Tennis
  • Coffee shop
  • Microwave
  • Refrigerator
  • Breakfast in the room
  • Kids' club
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Drop Anchor Resort and Marina

3-star Hotel with prices starting at $308 (before taxes) - See All Prices
A Great Hotel for the Ultimate 3 Days in Islamorada
  • Great Value: the price is lower than average for 3-star hotels.
  • Beach
  • Outdoor pool
  • Heated pool
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A great place to stay is Drop Anchor Resort and Marina which has nice rooms starting at $308. Offering an outdoor pool, rooms with kitchens, rooms with kitchenettes, golf, and free parking, it also has a great guest rating of 8.30 out of 10 from many previous guests. It's located at PO Box 222. This fun hotel is also nice because it offers bicycle rental, fishing, family rooms, a heated pool, and tennis which weekend visitors will enjoy. Also, it's just 2.6 miles from the city center. Don't forget that there's a kitchen in the room to cook your meals, too. It's also less than the average price for weekend trip hotels, so it's a great value.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Kitchen
  • Bicycle rental
  • Beach
  • Golf
More Great Amenities
  • Kitchenette
  • Free parking
  • Fishing
  • Family rooms
  • Heated pool
  • Tennis
  • Microwave
  • Refrigerator
  • Saltwater pool
View Prices and Reviews


Pines & Palms Resort

3-star Resort with prices starting at $333 (before taxes) - See All Prices
Perfect for 2 Days in Islamorada
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.
  • Beach
  • Outdoor pool
  • Heated pool
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We found Pines & Palms Resort to be a great place to stay, and the price starts at $333. We loved that is has an outdoor pool, a pool bar, room service, snorkeling, and a bar, and it also has a terrific guest rating of 8.90 out of 10 from previous guests. It's located at 80401 Old Highway. You'll also find rooms with kitchens, rooms with kitchenettes, child care, free parking, and evening entertainment which weekend travelers will love. And this comfortable hotel is just 2 miles from the center of town. We always love having a pool, and the one here is really nice. It's a great value, too, because it's less than the average price for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Snorkeling
  • Kitchen
  • Bicycle rental
  • Beach
  • Golf
More Great Amenities
  • Pool bar
  • Bar/Lounge
  • Kitchenette
  • Babysitting / Child Care
  • Free parking
  • Fishing
  • Family rooms
  • Heated pool
  • Microwave
  • Refrigerator
View Prices and Reviews


Islander Resort Bayside

3-star Hotel with prices starting at $266 (before taxes) - See All Prices
A Great Weekend Getaway Hotel
  • Great Value: the price is lower than average for 3-star hotels.
  • Beach
  • Outdoor pool
  • Heated pool
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With terrific rooms from $266, Islander Resort Bayside, at 81450 Overseas Hwy provides an outdoor pool, scuba diving, snorkeling, rooms with kitchens, and rooms with kitchenettes. Its terrific guest rating is 8.60 out of 10 from previous guests staying here. Travelers will really like this relaxing hotel which also offers laundry services, free parking, laundry facilities, bicycle rental, and fishing. It's located just 0.9 miles from the city center, too. Having a kitchenette is a nice way for you to have some meals in the room, too. It's a great value, as the price is less than the average for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Snorkeling
  • Kitchen
  • Bicycle rental
  • Beach
  • Golf
More Great Amenities
  • Kitchenette
  • Laundry service
  • Free parking
  • Fishing
  • Family rooms
  • Heated pool
View Prices and Reviews


Chesapeake Beach Resort

3-star Resort with prices starting at $249 (before taxes) - See All Prices
A Terrific Hotel for a Long Weekend in Islamorada
  • Great Value: the price is lower than average for 3-star hotels.
  • Beach
  • Outdoor pool
  • Pets allowed
  • Spa
  • Heated pool
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Chesapeake Beach Resort has a great guest rating of 7.60 out of 10, and offers an outdoor pool, room service, parking, rooms with kitchenettes, and a free breakfast. The great rooms here start at $249 before taxes and depending on the season. It can be found at 83409 Overseas Highway. Furthermore, it also offers pet-friendly rooms, a hot tub, a spa, laundry facilities, and bicycle rental, which is nice for visitors. Just 1.2 miles from the city center, this terrific hotel is a terrific choice. Make sure to set aside some time for swimming in the pool, too. We found the price of this hotel to be a great value because the price is less than average for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Parking
  • Free breakfast
  • Pets allowed
  • Hot tub
  • Spa
  • Bicycle rental
  • Beach
  • Golf
More Great Amenities
  • Kitchenette
  • Fishing
  • Heated pool
  • Tennis
  • Microwave
  • Refrigerator
View Prices and Reviews


Fisher Inn Resort & Marina

Motel with prices starting at $263 (before taxes) - See All Prices
A Great Stay for a Weekend Escape
  • Great Value: the price is lower than average for 3-star hotels.
  • Beach
  • Outdoor pool
  • Pets allowed
  • Heated pool
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The great guest rating of Fisher Inn Resort & Marina is 8.40 out of 10. This place has an outdoor pool, room service, scuba diving, snorkeling, and breakfast. Prices for the terrific rooms are from $263, and it's located at 84951 Overseas Highway. We also love the rooms with kitchens, rooms with kitchenettes, laundry services, pet-friendly rooms, and free parking which are great for weekend visitors. And since it's just 2.5 miles from the center of the town, the location is great, too. It's always nice having a heated pool to relax in. The price of this hotel is less than average for weekend trip hotels, which makes it a great value.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Snorkeling
  • Breakfast included
  • Kitchen
  • Pets allowed
  • Beach
  • Golf
More Great Amenities
  • Kitchenette
  • Laundry service
  • Free parking
  • Table tennis
  • Fishing
  • Heated pool
  • Microwave
  • Refrigerator
View Prices and Reviews


Angler's Reef Resort

3-star Resort with prices starting at $574 (before taxes) - See All Prices
A Nice Option for a Weekend Retreat
  • High Quality: guest ratings are higher than average.
  • Beach
  • Outdoor pool
  • Heated pool
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A cool place is Angler's Reef Resort because it has great rooms that start at $574. It has an outdoor pool, scuba diving, snorkeling, rooms with kitchens, and child care, it also earned a great guest rating of 9.10 out of 10 from people who have stayed here before. It's found at 84977 Overseas Highway. Only 2.7 miles from the city center, weekend travelers will especially love free parking, laundry facilities, fishing, family rooms, and a heated pool at this fun hotel.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Snorkeling
  • Kitchen
  • Beach
  • Golf
More Great Amenities
  • Babysitting / Child Care
  • Free parking
  • Fishing
  • Family rooms
  • Heated pool
  • Microwave
  • Refrigerator
View Prices and Reviews


Islander Resort

3-star Resort with prices starting at $267 (before taxes) - See All Prices
Perfect Hotel for a 3-day trip in Islamorada
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.
  • Beach
  • Family-Friendly
  • Outdoor pool
  • Heated pool
View Prices on Kayak
See Location

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Islander Resort offers an outdoor pool, a pool bar, a restaurant, snorkeling, and a bar which we really like. The terrific rooms here start at $267 (before taxes). It's located at 82100 Overseas Hwy and has earned a guest rating of 8.90/10. This comfortable hotel is also nice because it offers rooms with kitchens, laundry services, a child pool, free parking, and kids meals which travelers will enjoy. Also, it's just 0.3 miles from the city center. Unwinding at the restaurant after sightseeing is a nice way to end the day. It's a great value, too, because it's less than the average price for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Snorkeling
  • Kitchen
  • Child pool
  • Bicycle rental
  • Beach
  • Family-Friendly
  • Golf
More Great Amenities
  • Pool bar
  • Restaurant
  • Bar/Lounge
  • Laundry service
  • Free parking
  • Table tennis
  • Fishing
  • Family rooms
  • Heated pool
  • Saltwater pool
View Prices and Reviews


Amara Cay Resort

4-star Hotel with prices starting at $255 (before taxes) - See All Prices
A Great Stay for a Weekend Trip to Islamorada
  • Great Value: the price is lower than average for 4-star hotels.
  • Beach
  • Family-Friendly
  • Outdoor pool
  • Pets allowed
  • Heated pool
View Prices on Kayak
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Located at 80001 Overseas Highway, Amara Cay Resort has great rooms from $255 (before taxes). It offers an outdoor pool, a pool bar, a restaurant, a fitness center, and snorkeling. It has a terrific 8.50 rating out of 10 from previous guests who have stayed here. You'll also find a bar, parking, pet-friendly rooms, kids meals, and laundry facilities which visitors will love. And this relaxing hotel is just 2.4 miles from the center of town. It's a great value, as the price is less than the average for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Snorkeling
  • Parking
  • Pets allowed
  • Bicycle rental
  • Beach
  • Family-Friendly
  • Golf
More Great Amenities
  • Pool bar
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Fishing
  • Family rooms
  • Heated pool
  • Microwave
  • Refrigerator
View Prices and Reviews


Topsider Resort by Capital Vacations

3-star Resort with prices starting at $327 (before taxes) - See All Prices
A Great Hotel for the Ultimate 3 Days in Islamorada
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.
  • Beach
  • Outdoor pool
  • Heated pool
View Prices on Kayak
See Location

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A great place to stay is Topsider Resort by Capital Vacations which has nice rooms starting at $327. Offering an outdoor pool, snorkeling, outdoor tennis, rooms with kitchens, and a hot tub, it also has a great guest rating of 9.40 out of 10 from many previous guests. It's located at 75500 Overseas Hwy. Weekend visitors will really like this terrific hotel which also offers free parking, fishing, family rooms, a heated pool, and a private pool. It's located just 6.9 miles from the city center, too. We found the price of this hotel to be a great value because the price is less than average for weekend trip hotels.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Snorkeling
  • Kitchen
  • Hot tub
  • Beach
  • Golf
More Great Amenities
  • Free parking
  • Fishing
  • Family rooms
  • Heated pool
  • Private pool
  • Microwave
  • Refrigerator
View Prices and Reviews


Also, take a look at the Weekend Trip hotels in nearby destinations: Key Largo and Marathon.

For more terrific hotel ideas in Islamorada, make sure you also see Best Family-Friendly Hotels in Islamorada, Best Beach Hotels in Islamorada, Best Pet-Friendly Hotels in Islamorada, Best Hotels for First Time Visitors in Islamorada, Best Hotels for One Week in Islamorada, Best Hotels for One Night in Islamorada, or Best Romantic Hotels for Couples in Islamorada.


How much do hotels for a weekend visit cost in Islamorada?

Islamorada Average Weekend Trip Hotel Price
$388

Visitors will find a large range of terrific weekend trip hotel choices when planning a visit to Islamorada, Florida. The price of these weekend trip hotels can vary according to location, type, and amenities. The average weekend trip hotel price in Islamorada, Florida based on data from 17 hotels is an affordable $388. If you're interested in more information about hotels here, see our guide to hotel prices in Islamorada.

The average prices of our suggested weekend trip hotels by star rating:

  • 4-star hotels: $257
  • 3-star hotels: $406


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