Hotels with Restaurants in Islamorada from $138
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Top Islamorada Hotels with Restaurants

Casa Morada
136 Madeira Road Islamorada FL
$456 nightly
The price is $513 total per night
$513 total
Dec 7 - Dec 8
Total with taxes and fees
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy a day at the beach kayaking, or relax with beach umbrellas. There's no skimping ...

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$280 nightly
The price is $316 total per night
$316 total
Dec 9 - Dec 10
Total with taxes and fees
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$178 nightly
The price is $201 total per night
$201 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$317 nightly
The price is $357 total per night
$357 total
Dec 17 - Dec 18
Total with taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

Pines & Palms Resort
80401 Old Hwy Islamorada FL
$188 nightly
The price is $212 total per night
$212 total
Dec 7 - Dec 8
Total with taxes and fees
The private beach and marina are among the highlights at this hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Enjoy the outdoor pool ...

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$250 nightly
The price is $282 total per night
$282 total
Dec 10 - Dec 11
Total with taxes and fees
A private beach and a restaurant are featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for ...

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$254 nightly
The price is $285 total per night
$285 total
Dec 17 - Dec 18
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$218 nightly
The price is $246 total per night
$246 total
Dec 15 - Dec 16
Total with taxes and fees
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$130 nightly
The price is $142 total per night
$142 total
Dec 7 - Dec 8
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area ...

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$123 nightly
The price is $138 total per night
$138 total
Dec 15 - Dec 16
Total with taxes and fees
A private beach and an outdoor pool are featured at this Art Deco motel. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. ...

Creekside Inn
90611 Old Highway Tavernier FL
Free Cancellation
Reserve now, pay when you stay
$125 nightly
The price is $141 total per night
$141 total
Dec 8 - Dec 9
Total with taxes and fees
This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. ...
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.
Islamorada hotels essential information
Accommodation | 2,241 hotels |
|---|---|
Lowest Price | $138 |
Highest Price | $513 |
Popular hotels | Amara Cay Resort, Islander Resort, Cheeca Lodge & Spa, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Creekside Inn, La Siesta Resort & Villas, Casa Morada, Conch On Inn Motel, Chesapeake Beach Resort, Fisher Inn Resort & Marina, Drop Anchor, Pines & Palms Resort |
Recent Islamorada hotel reviews by fellow wanderers

Cheeca Lodge & Spa
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Property is beautiful with tons of amenities. The room was very nice and overall we were very happy. Here are a few of the issues we had though for full transparency. The beach is sand, but it's hard in a way that's a bit unnatural and doesn't flow into the water. There were weddings on two nights we were there and the noise from the afterparty was loud in the rooms even with the doors shut. The noise went fairly late into the evening past when most places would have a noise curfew of sorts for the respect of other guests. The water temperature in the shower was either hard to control or broken as sometimes it was extremely hot and sometimes barely warm. The roof mounted fill for the outside tub was a neat feature, but it was very loud. When we checked in our room was not available. We were promised a call when it was ready, but never got one. We finally asked at the check in time and they said it was ready and we were supposed to have been given a call some time ago. We also noticed that every time we overheard the check-in information being given to a new guest, we heard information that had not been given to us. Parking was limited later in the evening and we struggled to find a spot. The alternative is to use valet, but I rarely opt for that unless it is required."
A verified traveler stayed at Cheeca Lodge & Spa
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