Best Islamorada Family Resorts

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Calm bay waters, boat excursions, and a happy-go-lucky vibe make Islamorada (and the rest of the Florida Keys) a great place for a family vacation. Here are Islamorada's best hotels for families, from an old-school luxury resort to a humble budget spot on the bay.

  1. In operation since 1946, the 214-room Cheeca Lodge & Spa has drawn plenty of high-profile guests over the years. In addition to celebrity cachet, this luxury resort boasts gorgeous and lush grounds and on-site features like a nine-hole golf course, a pretty beach, six tennis courts, and two pools (one for adults only). Three restaurants serve tasty seafood, sushi, and Italian fare -- but, like everything else here, they're pricey -- and a fun tiki bar is set on the beach. An environmentally-focused kids' club offers all sorts of activities, but it's not free. Spacious guest rooms with elegant tropical decor have private furnished balconies (some with outdoor jetted tubs), while suites add separate living rooms and some have full kitchens. The steep resort fee covers a lot, such as green fees, and use of bikes, kayaks, and fishing gear. 

  2. The waterfront Pelican Cove Resort Marina Hotel Islamorada underwent renovations in 2014, so feels more sleek and stylish than many area hotels. Pelican Cove's 63 sleek and stylish rooms come equipped with flat-screen TVs with cable, mini-fridges, coffeemakers, and private balconies with views of the marina or ocean. Standard rooms have either two queen-size beds or a king-size bed and a queen-size sleeper sofa. Families needing even more space could opt for a Junior Suite or a Suite with a separate bedroom, living room, and large oceanfront balconies. Beach chairs and towels are provided for use on the hotel's private beach, where kayaks, water bikes, and paddleboards are available. The hotel also offers an outdoor pool and hot tub, a tennis court, and an oceanfront bar/cafe (there's no full-service restaurant here, whereas Cheeca has multiple dining options). Pelican Cove charges a daily resort fee, which includes amenities like Wi-Fi, breakfast, parking, and non-motorized water sports. 

  3. Islander Resort is a mid-range hotel set on 22 oceanside acres, with maritime vibes and signature Guy Harvey artwork. The 114-room hotel's borderline kitsch style won't please everyone, but all visitors appreciate its beach (man-made), fishing pier, abundant water sports, two outdoor pools and hot tub, and waterside seafood restaurant and bar. The breakfast buffet is not included with room rates, however, and can be expensive -- for this reason, families might prefer Pelican Cove, where breakfast is "free" under the resort fee. Islander's oceanfront rooms and suites have vaulted ceilings, airy style, and screened-in patios that face the pool, garden, or ocean. Some units have picnic tables and barbecue grills outside. Rooms have kitchenettes, and suites come with full kitchens that include dishwashers, full-size refrigerators, microwaves, ovens, coffeemakers, and dining tables. Note that Islander Resort is closed until fall 2018.

  4. This 18-room resort is very much of the laid-back "Old Keys" style. It includes a man-made beach surrounded by thatched-roof umbrellas, hammocks, and palm trees, but the area is for boat launching and docking, not swimming. A heated water-facing pool makes up for this, though families may prefer Islander's beach with games and water sports. Drop Anchor's rooms are spread over several low-lying pastel buildings, and include air-conditioning, free Wi-Fi, flat-screen TVs with premium channels, and coffeemakers. Some have full kitchens, private balconies or patios, and ocean views, but by and large they are low on frills.

  5. Located directly on the ocean, Amara Cay provides ample access to water sports, including boating, fishing, diving, and kayaking. The hotel has its own boat dock and dive shop that offers full dive certification programs and refresher courses. A property-wide renovation completed in 2015 transformed what was once a typical value hotel chain into beachy-chic resort with modern rooms and facilities. Like the shore at Drop Anchor, the beach here is more for boating than swimming, but a heated lagoon pool faces the water.

  6. This picturesque venue -- a frequent spot for weddings -- consists of 16 individually decorated one- to three-bedroom homes, each one with an impressive and modern kitchen, washer/dryer, gas barbecue grill, flat-screen TV with cable, and free Wi-Fi. Guests are typically families and groups of friends, who tend to hang out on their home's private porch or around the outdoor pool and hot tub, where the heated rocks create a microclimate that encourages growth of the surrounding gardens. As downsides, Caribbean Resort lacks a beach and an on-site restaurant, and its nightly rates far surpass those of any other pick on this list.

  7. The mid-range Chesapeake Beach Resort could stand some upgrades here and there, but overall it is a decent and laid-back pick for families. On the hotel's private beach, guests get unlimited use of non-motorized water-sports equipment (covered by the mandatory resort fee). Activities include kayaking, sailing, and boating. On land, there are two heated pools, a hot tub, a tennis court, a shuffleboard court, and a children's playground. Other freebies include use of resort bicycles, Wi-Fi, daily continental breakfast, and parking. There isn't a restaurant or bar on-site, though there are several options within walking distance. 

  8. This 17-room budget hotel offers a simple, bayside stay that's ideal for families and boaters. The waters surrounding the Coral Bay are excellent for fishing and snorkeling, and many guests park their boats right at the hotel for free. Rooms are clean and spacious, with flat-screen TVs and microwaves, but the style is simple and dated -- expect to see tropical floral prints and faded wall art. Sunset views are great, and the atmosphere is laid-back, but the low(ish) rates here mean few frills.

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