Romantic Hotels in Islamorada, FL
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Top Islamorada Romantic Getaways & Hotels
Casa Morada
136 Madeira Road Islamorada FL
$482 nightly
The price is $543 total per night
$543 total
Jan 5 - Jan 6, 2026
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 ...
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$328 nightly
The price is $370 total per night
$370 total
Jan 4 - Jan 5, 2026
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 ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$228 nightly
The price is $257 total per night
$257 total
Jan 5 - Jan 6, 2026
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
$347 nightly
The price is $391 total per night
$391 total
Jan 12 - Jan 13, 2026
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 ...
Pines & Palms Resort
80401 Old Hwy Islamorada FL
$308 nightly
The price is $347 total per night
$347 total
Jan 4 - Jan 5, 2026
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 ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$305 nightly
The price is $343 total per night
$343 total
Jan 4 - Jan 5, 2026
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 ...
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$229 nightly
The price is $258 total per night
$258 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
Free beach cabanas, a waterfront location, and more await visiting couples at this romantic hotel.
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$271 nightly
The price is $305 total per night
$305 total
Jan 6 - Jan 7, 2026
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 ...
Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$316 nightly
The price is $356 total per night
$356 total
Jan 7 - Jan 8, 2026
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 ...
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$191 nightly
The price is $210 total per night
$210 total
Jan 4 - Jan 5, 2026
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
$392 nightly
The price is $442 total per night
$442 total
Jan 3 - Jan 4, 2026
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
$191 nightly
The price is $215 total per night
$215 total
Jan 5 - Jan 6, 2026
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 | 2,220 hotels |
|---|---|
Lowest Price | $210 |
Highest Price | $543 |
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
Chesapeake Beach Resort
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"It was a great breakfast.... they had everything that i liked in particular. They had healthy options.. not a big place so it didnt seem overwhelmed with options just the right amount of options. Place i staid had an amazing ocean view :) "
A verified traveler stayed at Chesapeake Beach Resort
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