Hotels with Entertainment in Upper Matecumbe Key, FL

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  3.  USA
  4.  Florida
  5.  Upper Matecumbe Key
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Explore 67 Hotels with Entertainment in Upper Matecumbe Key from $202

Cheeca Lodge & Spa
Cheeca Lodge & Spa
Resort
Islamorada, FL, USA
0.3k from Upper Matecumbe Key center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, Golf, Romantic, 5-star

8.7

Fabulous

977 reviews

$865
Average price / night
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Islander Resort
Islander Resort
Resort
Islamorada, FL, USA
0.6k from Upper Matecumbe Key center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Beach

8.7

Fabulous

1451 reviews

$348
Average price / night
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La Jolla Resort
La Jolla Resort
Hotel
Islamorada, FL, USA
1.0k from Upper Matecumbe Key center

B&bs, Accommodations, Pools, Parking, Inns, Lodgings, Beach, Places to stay, Family

8.8

Fabulous

906 reviews

$270
Average price / night
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Sunset Inn
Sunset Inn
Hotel
82200 Overseas Hwy, Islamorada, FL, 33036-3637, United States
0.9k from Upper Matecumbe Key center

AC, Barbecue, Crib, Free Parking, Heater, Housekeeping, Internet, No Smoking, Outdoor Space

9.2

Superb

1001 reviews

$232
Average price / night
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Hadley Resort and Marina
Hadley Resort and Marina
Hotel
Islamorada, FL, USA
1.6k from Upper Matecumbe Key center

Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Beach, Places to stay, Family

7.1

Good

1125 reviews

$202
Average price / night
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Bayside Villas by Islander Resort
Bayside Villas by Islander Resort
Hotel
81450 Overseas Highway, Islamorada, FL, 33036, United States
0.9k from Upper Matecumbe Key center

AC, Balcony, Bar, Barbecue, Crib, Elevator, Free Parking, Housekeeping, Internet

8.8

Fabulous

416 reviews

$446
Average price / night
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The Islands of Islamorada
The Islands of Islamorada
Hotel
Islamorada, FL, USA
1.8k from Upper Matecumbe Key center

Luxury, Accommodations, Pools, Parking, 4-star, Lodgings, Beach, Hot tubs, Places to stay

9.3

Superb

17 reviews

$795
Average price / night
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Casa Morada
Casa Morada
Hotel
136 Madeira Road, Islamorada, FL, 33036, United States
0.9k from Upper Matecumbe Key center

AC, Breakfast Included, Free Parking, Housekeeping, Internet, Outdoor Space, Pool, Room Service, TV

9.4

Superb

431 reviews

$554
Average price / night
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Pines & Palms Resort
Pines & Palms Resort
Resort
Upper Matecumbe Key, Florida, USA
2.1k from Upper Matecumbe Key center

Accommodations, Pools, Resorts, Parking, Romantic, 3-star, Lodgings, Beach, Places to stay

9.0

Fabulous

762 reviews

$282
Average price / night
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La Siesta Resort & Villas
La Siesta Resort & Villas
Hotel
Islamorada, FL, USA
2.2k from Upper Matecumbe Key center

Accommodations, Pools, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Beach, Places to stay

8.3

Very Good

339 reviews

$240
Average price / night
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Amara Cay Resort
Amara Cay Resort
Hotel
Islamorada, FL, USA
2.8k from Upper Matecumbe Key center

Accommodations, Pools, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Beach, Places to stay

8.1

Very Good

607 reviews

$254
Average price / night
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Chesapeake Beach Resort
Chesapeake Beach Resort
Resort
Islamorada, FL, USA
3.1k from Upper Matecumbe Key center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

8.0

Good

846 reviews

$536
Average price / night
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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Resort
Islamorada, FL, USA
4.0k from Upper Matecumbe Key center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

8.4

Very Good

26 reviews

$649
Average price / night
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Sands of Islamorada
Sands of Islamorada
Hotel
80051 Overseas Highway, Islamorada, FL, 33036, United States
2.6k from Upper Matecumbe Key center

AC, Barbecue, Crib, Extra Bed, Free Parking, Housekeeping, Internet, Laundry, Microwave

8.8

Fabulous

406 reviews

$263
Average price / night
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Coconut Cove Resort & Marina
Coconut Cove Resort & Marina
Hotel
Upper Matecumbe Key, Florida, USA
4.9k from Upper Matecumbe Key center

B&bs, Accommodations, Pools, Parking, Inns, Lodgings, Places to stay, Family, Accessible hotels

7.8

Good

248 reviews

$220
Average price / night
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Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
Hotel
Islamorada, FL, 33036, United States
2.8k from Upper Matecumbe Key center

AC, Arcade, Balcony, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

New to Booking
$513
Average price / night
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Best Place to Unwind! Free Parking, Onsite Pool, Short Drive to Anne's Beach
Best Place to Unwind! Free Parking, Onsite Pool, Short Drive to Anne's Beach
Hotel
Islamorada, FL, 33036, United States
2.8k from Upper Matecumbe Key center

AC, Arcade, Balcony, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

6.0

Review score

1 reviews

$513
Average price / night
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Relaxation at Its Finest in Islamorada! Free Parking, Swimming Pool!
Relaxation at Its Finest in Islamorada! Free Parking, Swimming Pool!
Hotel
Islamorada, FL, 33036, United States
2.8k from Upper Matecumbe Key center

AC, Arcade, Balcony, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

8.0

Good

1 reviews

$632
Average price / night
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Home Away from Home in Islamorada! Pets Allowed, Free Parking, Outdoor Pool!
Home Away from Home in Islamorada! Pets Allowed, Free Parking, Outdoor Pool!
Hotel
Islamorada, FL, 33036, United States
2.8k from Upper Matecumbe Key center

AC, Arcade, Balcony, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

New to Booking
$632
Average price / night
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High Tides and Good Vibes! 2 Relaxing Units, Pet-friendly Property, Pool
High Tides and Good Vibes! 2 Relaxing Units, Pet-friendly Property, Pool
Hotel
Islamorada, FL, 33036, United States
2.8k from Upper Matecumbe Key center

AC, Arcade, Balcony, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

New to Booking
$1181
Average price / night
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Comfort and Relaxation! Free Parking, Minutes to History of Diving Museum
Comfort and Relaxation! Free Parking, Minutes to History of Diving Museum
Hotel
Islamorada, FL, 33036, United States
2.8k from Upper Matecumbe Key center

AC, Arcade, Balcony, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

New to Booking
$520
Average price / night
Check Availability

Pro Tip for Travelers:
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Upper Matecumbe Key Hotels with Entertainment on the Map

Frequently Asked Questions

Entertainment offerings may include live music, cultural shows, game rooms, or on-site events depending on the hotel’s category and facilities.

Some hotels include basic entertainment at no extra cost, while others may charge separately for premium shows or special events.

Hotels with entertainment in Upper Matecumbe Key generally start from around $202 per night, depending on the level of facilities and activities offered.

Yes, many entertainment-focused hotels are designed for families and groups, offering activities suitable for both adults and children.

Along with entertainment options, many properties also offer Entertainment, Pool, and Guest Services for a more complete stay experience.