Welcome to a one-of-a-kind place of possibilities. With fifteen waterfront acres of invigorating adventure and idyllic relaxation, our Islamorada, Florida, resort is a family-friendly place of easygoing enjoyment and simple pleasures, with a variety of bright, island-inspired guestrooms and cottages. And The Cove, an adult-centric resort-within-a-resort, features a tranquil, private beach lagoon. All around, you’ll see the tropical beauty and feel the authentic spirit of the Keys. Enjoy nine distinctive culinary offerings, from the woodsmoke warmth of Kindler to the legendary Tiki Bar. Here in Islamorada, the “Sport Fishing Capital of the World,” the expertise of seasoned fishermen and a full-service marina await serious anglers and curious newcomers alike. Whether you’re looking for unparalleled fishing, family fun in the sun, a romantic getaway, an upscale corporate retreat, or an unforgettable seaside event, Three Waters Resort & Marina offers the ultimate Florida Keys experience.
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.8 km) from Keys History & Discovery Center.
Spend the day on the private beach or dip into one of the 2 outdoor swimming pools.
Featured amenities include a computer station, a 24-hour front desk, and multilingual staff.
Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Cable television is provided for your entertainment. Private bathrooms with showers feature designer toiletries and hair dryers.
GGuest User2023.08.06
Very bad experience I paid for a room with 2 beds and they gave me a room with an air bed and their answer was that everything was full and there were no towels in the pool I asked no one answered the beach very bad
With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum. This beach hotel is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1 mi (1.6 km) from Matecumbe United Methodist Church.
Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands.
A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM.
Featured amenities include a business center, express check-out, and multilingual staff. Free self parking is available onsite.
Make yourself at home in one of the 37 air-conditioned rooms featuring refrigerators. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers.
49 review
3.7/5
Price from
CAD 146
per night
Check Availability
You Might Like
Hotels With BreakfastHotels With Twin RoomHotels With 1 Double BedHotels With Swimming PoolHotels With Free Cancellation
With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery Center. This beach hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.7 mi (1.1 km) from History of Diving Museum.
Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a picnic area.
The front desk is staffed during limited hours. Limited parking is available onsite.
Make yourself at home in one of the 20 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with showers are provided. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center. This hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.3 km) from History of Diving Museum.
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills.
Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite.
Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and bidets. Conveniences include laptop-compatible safes and coffee/tea makers, and housekeeping is provided daily.
With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 9 minutes by foot from Keys History & Discovery Center. This beach hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.9 mi (1.4 km) from Florida Keys Brewing Co..
Pamper yourself with onsite massages or enjoy recreation amenities such as an outdoor pool. Additional features at this hotel include complimentary wireless internet access and concierge services.
Grab a bite from the snack bar/deli, or stay in and take advantage of the hotel's room service (during limited hours). Relax with your favorite drink at the bar/lounge or the poolside bar. A complimentary continental breakfast is served daily from 7 AM to 11 AM.
Featured amenities include complimentary newspapers in the lobby, dry cleaning/laundry services, and luggage storage. Free self parking is available onsite.
Make yourself at home in one of the 16 individually decorated guestrooms, featuring minibars and DVD players. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have designer toiletries and hair dryers.
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 9 minutes by foot from Islamorada Brewery & Distillery. This beach hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.2 km) from Florida Keys Brewing Co..
Spend the day on the private beach or dip into one of the 2 outdoor swimming pools. Additional features at this hotel include complimentary wireless internet access, gift shops/newsstands, and wedding services.
Satisfy your appetite at Tides Beachside Bar&Grill, one of the hotel's 2 restaurants. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar. Full breakfasts are available daily from 7:00 AM to 11:00 AM for a fee.
Featured amenities include a 24-hour front desk, multilingual staff, and laundry facilities. Planning an event in Islamorada? This hotel has 2760 square feet (256 square meters) of space consisting of conference space and 2 meeting rooms. Free self parking is available onsite.
Make yourself at home in one of the 114 guestrooms featuring iPod docking stations and Smart televisions. Rooms have private lanais. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms have complimentary toiletries and hair dryers.
GGuest User2023.08.23
Nice hotel rooms that you can drive up to. Nice amount of space—although the bathroom is very small. Pool area is ok, not enough umbrellas. Didn’t get water everyday despite being told it was included with the resort fee. The access to the sea isn’t great. Yoga was fantastic.
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing Co.. This beach resort is 0.3 mi (0.6 km) from MoradaWay Arts & Cultural District and 0.4 mi (0.6 km) from Hurricane Monument.
Relax at the full-service spa, where you can enjoy massages, body treatments, and facials. You can get some exercise with a round of golf or enjoy a lazy day at the private beach. This resort also features concierge services, babysitting (surcharge), and an arcade/game room.
Grab a bite at Atlantics Edge, one of the resort's 3 restaurants, or stay in and take advantage of the 24-hour room service. Snacks are also available at the coffee shop/cafe. Wind down with a drink at one of the 2 bars/lounges or 2 poolside bars. Full breakfasts are available daily from 7:00 AM to 11:00 AM for a fee.
Featured amenities include a business center, limo/town car service, and express check-out. Planning an event in Islamorada? This resort has 10000 square feet (929 square meters) of space consisting of conference space and 5 meeting rooms. Free valet parking is available onsite.
Stay in one of 243 guestrooms featuring LED televisions. Rooms have private balconies. Cable television is provided for your entertainment. Private bathrooms have designer toiletries and hair dryers.
LLuengoRUP2023.09.26
Great trip! We enjoyed it a lot! Great service, we love our room (ocean front) the only issue that we had is that we didn’t have access to internet through wifi
With a stay at Islander Bayside Villas and Boatslips, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 7 minutes by foot from Florida Keys Brewing Co.. This beach hotel is 0.4 mi (0.7 km) from MoradaWay Arts & Cultural District and 0.5 mi (0.9 km) from Matecumbe United Methodist Church.
Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, a picnic area, and complimentary use of a nearby fitness facility.
The front desk is staffed during limited hours. Free self parking is available onsite.
Make yourself at home in one of the 25 guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Your pillowtop bed comes with premium bedding, and all rooms are furnished with queen sofa beds. Rooms have private furnished balconies. 55-inch LCD televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected.
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center. This beach resort is 1 mi (1.7 km) from Hurricane Monument and 1.3 mi (2.1 km) from Florida Keys Brewing Co..
Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and bicycles to rent. Additional amenities at this resort include wireless internet access (surcharge), wedding services, and a picnic area. Guests can catch a ride to nearby destinations on the complimentary area shuttle.
Take advantage of the resort's room service (during limited hours). Quench your thirst with your favorite drink at the poolside bar. Cooked-to-order breakfasts are available daily from 7:00 AM to 11:00 AM for a fee.
Featured amenities include a 24-hour front desk and a water dispenser.
Make yourself at home in one of the 55 individually decorated guestrooms, featuring kitchenettes with refrigerators and microwaves. Your pillowtop bed comes with Egyptian cotton sheets. Wireless internet access (surcharge) keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, as well as safes and desks.
Very Good
55 review
4.1/5
Price from
CAD 191
per night
Check Availability
See All Hotels Near Rain Barrel Village
Top Pick Hotels near Rain Barrel Village
See all
Check out our most booked hotels near Rain Barrel Village from the past 30 days!
No.1
4.3/5
2 review
Treasure Harbor
Islamorada | 0.32KM from Rain Barrel Village
"Good Location"
Select dates to view prices
No.2
3.8/5
102 review
Fisher Inn Resort & Marina
Islamorada | 2.92KM from Rain Barrel Village
"Good Location"
Select dates to view prices
No.3
4.5/5
47 review
Ragged Edge Resort & Marina
Islamorada | 0.56KM from Rain Barrel Village
"Good Location"
Select dates to view prices
No.4
4.4/5
48 review
Sunset Inn
Islamorada | 7.13KM from Rain Barrel Village
"Good Location"
Select dates to view prices
No.5
3.7/5
49 review
Hadley Resort and Marina
Islamorada | 6.44KM from Rain Barrel Village
"Good Location"
Select dates to view prices
No.6
4.3/5
53 review
La Jolla Resort
Islamorada | 6.99KM from Rain Barrel Village
"Good Location"
Select dates to view prices
No.7
4.3/5
101 review
Islander Resort
Islamorada | 7.39KM from Rain Barrel Village
"Good Location"
Select dates to view prices
No.8
4.4/5
102 review
Cheeca Lodge & Spa
Islamorada | 7.9KM from Rain Barrel Village
"Good Location"
Select dates to view prices
Latest Reviews for Islamorada hotels
See all
Explore genuine reviews and ratings from real travellers to find the perfect accommodation for your needs.
4.2/5
Very Good
GGuest UserWe stopped for one night on our way to Key West. I wish we booked more nights here. We had a great stay. Aaron at the front desk was extremely helpful at checkin. He was very friendly and personable. This hotel is lucky to have him as a part of their front desk team. The lobby was beautiful with great views. We had a lot of fun playing with the complimentary games provided. We spend most of our time at the pool, which was large and lovely. Great views. The Tiki Bar made awesome drinks, one of the best pina colada’s that I ever had. We ate dinner there too, which worked out so well because our kids could keep playing at the pool and we all had fun after playing games outside. Room was large and comfortable. Breakfast the next day…really good! Try the breakfast panini sandwich, you won’t regret it! I see people talking about the resort fee. When you consider this hotel doesn’t charge for parking or wifi, offers complimentary kayak and paddle board rentals, a shuttle between their hotel and sister hotel with access to these amenities too… the resort fee is not so expensive. I’ve stayed at hotels with resort fees that charge extra for parking and internet, and include NO amenities except access to a pool and workout facility. At least this hotel gives you something for the money you spend. Thank you for a great stay, we will absolutely be back. For longer next time!
GGuest UserVery bad experience I paid for a room with 2 beds and they gave me a room with an air bed and their answer was that everything was full and there were no towels in the pool I asked no one answered the beach very bad
What's the average price of hotels near Rain Barrel Village this weekend?
According to Trip.com's data, the average price for a weekend night at hotels near Rain Barrel Village in Islamorada is CAD 647. Prices fluctuate often; this rate is for reference only.
What hotels near Rain Barrel Village offer breakfast?
What's the average price per night of hotels near Rain Barrel Village?
According to Trip.com's data, the average price per night at hotels near Rain Barrel Village in Islamorada is CAD 1,178. Prices fluctuate often; this rate is for reference only.
Which hotels near Rain Barrel Village have free Wi-Fi?
Since staying fit is important to a lot of guests, it's no surprise that gyms can be found in many hotels.
Coconut Cove Resort & Marina
is a popular hotel with a gym.
What are some accessible hotels near Rain Barrel Village?