Matecumbe Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
Islander Resort
82100 Overseas Highway Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
La Jolla Resort
82216 Overseas Highway Islamorada FL
Stay at this hotel in Islamorada. Enjoy free WiFi, a private beach, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
The Islands of Islamorada
82779 Old Hwy Islamorada FL
Book a stay at this luxury hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
Casa Morada
82200 overseas HWY Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Matecumbe Resort
76261 Overseas Hwy Islamorada FL
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, free parking, and a private beach. Popular attractions Robbie’s of Islamorada and Indian Key ...
Caloosa Cove Resort by CoolVacay
73801 Overseas Hwy Islamorada FL
Stay at this condo in Islamorada. Enjoy free WiFi, free parking, and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.
Pines & Palms Resort
80401 Old Hwy Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
The Caribbean Resort
117 Carroll St Islamorada FL
Book a stay at this family-friendly hotel in Islamorada. Enjoy a marina, free bicycles on site, and daily housekeeping. Popular attractions Lorelei Restaurant ...
Sunset Inn
82200 Overseas Hwy Islamorada FL
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the pool and the helpful staff in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 21 - Mon, Nov 2
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$73
Roundtrip
found 1 day ago
Tue, Nov 10 - Sat, Nov 14
BOS
Logan Intl.
MIA
Miami Intl.
$159
Roundtrip
found 3 hours ago
Fri, Nov 13 - Tue, Nov 17
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$159
Roundtrip
found 2 days ago
Mon, Dec 7 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$179
Roundtrip
found 1 day ago
Sat, Nov 14 - Wed, Dec 2
BOS
Logan Intl.
MIA
Miami Intl.
$214
Roundtrip
found 4 days ago
Best points of interest in Islamorada
- Anne's Beach Vacations
- Robbie’s of Islamorada Vacations
- Bud n' Mary's Dive Center Vacations
- Florida Keys Brewing Co. Vacations
- Islamorada Brewery & Distillery Vacations
- Sunset Drive Beach Vacations
- History of Diving Museum Vacations
- Hurricane Monument Vacations
- MoradaWay Arts & Cultural District Vacations
- Lorelei Restaurant & Cabana Bar Vacations
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