A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Photo by Cameron Abbott

Upper Matecumbe Key Romantic Vacations

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    • Top Romantic vacation packages in Upper Matecumbe Key

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    Discover the most popular places to visit in Upper Matecumbe Key

    A marina with boats docked, a motel, and a cafe.

    Bud n' Mary's Dive Center

    Rating: 8.8/10 (504 reviews)

    Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.

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    A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

    Florida Keys Brewing Co.

    Rating: 9.2/10 (520 reviews)

    You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

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    A building with a blue facade, a large mural of a diving scene, and a statue of a diver.

    History of Diving Museum

    Rating: 9.0/10 (177 reviews)

    Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

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    A stone monument with a relief sculpture, surrounded by palm trees and a clear blue sky.

    Hurricane Monument

    Rating: 8.6/10 (250 reviews)

    The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

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    Islamorada Brewery & Distillery

    Rating: 9.4/10 (8 reviews)

    You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

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    beach near Islamorada

    Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?

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    Lorelei Restaurant & Cabana Bar

    After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.

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    MoradaWay Arts & Cultural District

    Enjoy an outing to MoradaWay Arts & Cultural District during your stay in Islamorada.

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    Top Romantic Upper Matecumbe Key Hotels

    Chesapeake Beach Resort

    A beach with palm trees and lounge chairs.
    • Address: 83409 Overseas Hwy, Islamorada, FL, 33036, US
    • Location: Matecumbe, 2.8 km from Upper Matecumbe Key
    • Star rating: 3.5/5
    • Guest rating: 9.4/10 (Exceptional, 1824 reviews)
    • Price: CA $220, CA $327 total, includes taxes & fees, Nov 15 - Nov 16, for Top Romantic Upper Matecumbe Key Hotels
    • Review: Perfecta instalación para pasarse unos días magnífico

    La Jolla Resort

    A covered outdoor area with wooden furniture, a table with a candle, and a view of the ocean.
    • Address: 82216 Overseas Highway, Islamorada, FL, 33036, US
    • Location: Matecumbe, 0.8 km from Upper Matecumbe Key
    • Star rating: 2.5/5
    • Guest rating: 9.2/10 (Wonderful, 1003 reviews)
    • Price: CA $169, CA $230 total, includes taxes & fees, Nov 15 - Nov 16, for Top Romantic Upper Matecumbe Key Hotels
    • Review: Very nice property on the water. Beautifully sunset location. We were upgraded to the SOL house which was gorgeous.

    Islander Resort

    A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
    • Address: 82100 Overseas Highway, Islamorada, FL, 33036, US
    • Location: Matecumbe, 0.4 km from Upper Matecumbe Key
    • Star rating: 4/5
    • Guest rating: 9.4/10 (Exceptional, 1170 reviews)
    • Price: CA $297, CA $438 total, includes taxes & fees, Nov 15 - Nov 16, for Top Romantic Upper Matecumbe Key Hotels

    Amara Cay Resort

    A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
    • Address: 80001 Overseas Hwy, Islamorada, FL, 33036, US
    • Location: Matecumbe, 3 km from Upper Matecumbe Key
    • Star rating: 4/5
    • Guest rating: 8.8/10 (Excellent, 1332 reviews)
    • Price: CA $233, CA $366 total, includes taxes & fees, Nov 17 - Nov 18, for Top Romantic Upper Matecumbe Key Hotels
    • Review: If I have one complaint, it would be access to a decent cup of coffee. You would think there would be a quick access coffee shop or station or at least through the bar.

    Breezy Palms Resort

    A beach with thatched umbrellas, palm trees, and lounge chairs.
    • Address: 80015 Overseas Highway, Islamorada, FL, 33036, US
    • Location: Matecumbe, 2.9 km from Upper Matecumbe Key
    • Star rating: 2.5/5
    • Guest rating: 9/10 (Wonderful, 785 reviews)
    • Price: CA $163, CA $206 total, includes taxes & fees, Nov 15 - Nov 16, for Top Romantic Upper Matecumbe Key Hotels
    • Review: Rooms werent cleaned daily however the facilities were clean. Beach and pool on-site were excellent

    Cheeca Lodge & Spa

    A hotel courtyard with palm trees, a tiled walkway, and a building entrance.
    • Address: 81801 Overseas Highway, Mile Marker 82, Islamorada, FL, 33036, US
    • Location: Matecumbe, 0.1 km from Upper Matecumbe Key
    • Star rating: 5/5
    • Guest rating: 9.2/10 (Wonderful, 1518 reviews)
    • Price: CA $259, CA $395 total, includes taxes & fees, Nov 16 - Nov 17, for Top Romantic Upper Matecumbe Key Hotels

    Hadley Resort and Marina

    An outdoor seating area with wicker furniture and umbrellas, surrounded by palm trees and a building with a white exterior.
    • Address: 82749 Overseas Hwy, Islamorada, FL, 33036, US
    • Location: Matecumbe, 1.3 km from Upper Matecumbe Key
    • Star rating: 3.5/5
    • Guest rating: 7.6/10 (Good, 1001 reviews)
    • Price: CA $191, CA $263 total, includes taxes & fees, Nov 29 - Nov 30, for Top Romantic Upper Matecumbe Key Hotels

    La Siesta Resort & Villas

    Two people floating on inflatable rings in a clear pool.
    • Address: 80241 Overseas Highway, Islamorada, FL, 33036, US
    • Location: Matecumbe, 2.4 km from Upper Matecumbe Key
    • Star rating: 4/5
    • Guest rating: 8.6/10 (Excellent, 1003 reviews)
    • Price: CA $221, CA $353 total, includes taxes & fees, Nov 17 - Nov 18, for Top Romantic Upper Matecumbe Key Hotels
    • Review: "The hotel was cute, the room was nice and beds comfy. They need to replace their a few things my refrigerator wasn’t fully closing and the entire bottom was full rust and looked damaged. The bathroom sink has lots of rust. The communication with front end staff and house keeping wasn’t well. I had a late check out 12pm and from 10-11:30 I had 3 different house keepers asking if I was leaving so they can turn over the room for the next guest. The balcony was full of spider webs so seems they...

    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.

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    Plan unforgettable romantic Upper Matecumbe Key vacations

    What are some of the benefits of booking a romantic Upper Matecumbe Key vacation?

    When booking a romantic Upper Matecumbe Key vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Matecumbe.

    How can I find the best vacation packages for couples?

    If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Upper Matecumbe Key destination, and you'll be met with an array of options for you and your partner to enjoy.

    Can I find cheap romantic vacations for 2 in Upper Matecumbe Key?

    Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,894 and can enjoy savings of up to 17 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

    What do I need to consider when booking a romantic getaway in Upper Matecumbe Key?

    Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Upper Matecumbe Key certainly come in handy here.

    What amenities should I look for in a luxury romantic vacation?

    If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Upper Matecumbe Key.

    Can I book a romantic Upper Matecumbe Key vacation with a hot tub?

    Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

    How can I find romantic vacation getaways that are all-inclusive?

    An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Upper Matecumbe Key search.

    Can I book a romantic trip to Upper Matecumbe Key that is fully refundable?

    Several romantic Upper Matecumbe Key vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

    Why should I book a romantic vacation with Expedia?

    Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.

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