Romantic Hotels in Islamorada, FL
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Top Islamorada Romantic Getaways & Hotels

Casa Morada
136 Madeira Road Islamorada FL
$456 nightly
The price is $513 total per night
$513 total
Dec 15 - Dec 16
Total with taxes and fees
Fall in love again at this adults-only hotel. You and your special someone are sure to love the in-room massages, garden, and luxury bedding. You'll also appreciate ...

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$218 nightly
The price is $246 total per night
$246 total
Dec 10 - Dec 11
Total with taxes and fees
A private beach and premium mattresses await at this romantic hotel, which also offers 2 outdoor pools and a white sand beach.

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$301 nightly
The price is $339 total per night
$339 total
Dec 18 - Dec 19
Total with taxes and fees
Book a stay at this romantic hotel, featuring ocean-view dining and a garden. Couples will appreciate the champagne service, romance packages, and beach ...

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$298 nightly
The price is $336 total per night
$336 total
Dec 15 - Dec 16
Total with taxes and fees
A spa, in-room massages, and ocean-view dining await visiting couples at this upscale resort. The property also offers a garden, a hot tub, and a private beachfront ...

Pines & Palms Resort
80401 Old Hwy Islamorada FL
$248 nightly
The price is $279 total per night
$279 total
Dec 10 - Dec 11
Total with taxes and fees
A garden, a private beach, and luxury bedding await couples visiting this romantic hotel. The property also offers a terrace, an outdoor pool, and a waterfront ...

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 15 - Dec 16
Total with taxes and fees
Book a stay at this romantic resort, featuring ocean-view dining and a garden. Couples will appreciate the romance packages, premium mattresses, and Egyptian ...

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$271 nightly
The price is $304 total per night
$304 total
Dec 15 - Dec 16
Total with taxes and fees
A garden, poolside dining, and a private beach await couples looking for a romantic getaway at this Art Deco resort. The property also offers a terrace, 3 outdoor ...

Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$312 nightly
The price is $351 total per night
$351 total
Dec 18 - Dec 19
Total with taxes and fees
Premium mattresses, onsite dining, and luxury bedding await couples visiting this romantic hotel. The property also offers a terrace, an outdoor pool, and a ...

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$142 nightly
The price is $160 total per night
$160 total
Dec 10 - Dec 11
Total with taxes and fees
Free beach cabanas, a waterfront location, and more await visiting couples at this romantic hotel.

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$125 nightly
The price is $136 total per night
$136 total
Dec 10 - Dec 11
Total with taxes and fees
A garden and luxury bedding await visiting couples at this Art Deco hotel. The property also offers an outdoor pool and a waterfront location.

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$246 nightly
The price is $276 total per night
$276 total
Dec 14 - Dec 15
Total with taxes and fees
A private beach, premium mattresses, and Egyptian cotton sheets await couples visiting this romantic resort. The property also offers a terrace, an outdoor pool, ...

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $178 total per night
$178 total
Dec 18 - Dec 19
Total with taxes and fees
Love is in the air at this Art Deco motel, featuring a private beach, luxury bedding, and a terrace. Couples will love the outdoor pool and waterfront ...
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 | 2,234 hotels |
|---|---|
Lowest Price | $136 |
Highest Price | $513 |
Popular hotels | Cheeca Lodge & Spa, Chesapeake Beach Resort, Amara Cay Resort, Casa Morada, Islander Resort, Drop Anchor, Pines & Palms Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, La Siesta Resort & Villas, Bayside Villas by Islander Resort, Coconut Cove Resort and Marina, Fisher Inn Resort & Marina |
Recent Islamorada hotel reviews by fellow wanderers

Islander Resort
5 out of 5
Posted 10 hours ago
Travelocity Verified Review
"This resort was just what we needed. It started out with a small hicup, we checked in late and they gave our king bed room away. Front desk said something like Expedia oversells their property and there was nothing left that she could do. We had to take the double room. After a while my husband went on their website and found availability for a king bed, he showed the front desk and wow all of a sudden they had a king for us!
The resort was very relaxing, with an all inclusive Caribbean vibe minus the pushy water aerobics instructor trying to get you to participate lol! The food was good at the poolside bar and there was always staff walking around to take orders for drinks.
The rooms were really nice, clean and modern. The only negative was the vanity was really small with no room for toiletries. I had to carry everything in the bathroom with me when I was getting ready or washing my face at night.
I’m not sure if it was the time of year or what but the resort was not busy at all and felt very quiet and relaxing. You never had to fight for beach chairs or pool chairs. Lots of great restaurants a short drive away too."
A verified traveler stayed at Islander Resort
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