Find Romantic Hotels in Islamorada, FL
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check availability on Islamorada Romantic Hotels
Compare Islamorada Romantic Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Cheeca Lodge & Spa
Cheeca Lodge & Spa
9.0 out of 10, Wonderful, (1075)
The price is AED 737
AED 1,077 total
includes taxes & fees
21 May - 22 May

Chesapeake Beach Resort
Chesapeake Beach Resort
9.2 out of 10, Wonderful, (1456)
The price is AED 625
AED 909 total
includes taxes & fees
29 May - 30 May

Large Screened Porch, Professional Cleaning, Wifi
Large Screened Porch, Professional Cleaning, Wifi
9.4 out of 10, Exceptional, (96)

Amara Cay Resort
Amara Cay Resort
8.8 out of 10, Excellent, (1195)
The price is AED 780
AED 1,122 total
includes taxes & fees
18 May - 19 May

Casa Morada
Casa Morada
9.4 out of 10, Exceptional, (394)
The price is AED 1,466
AED 1,814 total
includes taxes & fees
18 May - 19 May

Islander Resort
Islander Resort
9.0 out of 10, Wonderful, (1006)
The price is AED 1,033
AED 1,394 total
includes taxes & fees
19 May - 20 May

Drop Anchor
Drop Anchor
8.8 out of 10, Excellent, (1000)
The price is AED 731
AED 951 total
includes taxes & fees
18 May - 19 May

Pines & Palms Resort
Pines & Palms Resort
9.2 out of 10, Wonderful, (990)
The price is AED 804
AED 1,107 total
includes taxes & fees
20 May - 21 May
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.
Find out more about Islamorada
Find out more about Islamorada
Recent reviews of Islamorada hotels
Recent reviews of Islamorada hotels

Chesapeake Beach Resort
5/5 Excellent
"Property was great . We booked the least expensive room and it was still a really nice room . Newly renovated clean comfy bed with fluffy pillows. Bathroom was small but still really nice . And it had a balcony with garden view. The complimentary Breakfast was delicious. Resort was beautiful pools were very nice beach was lovely . And they had glass bottom kayaks and paddle-board that were also included. . Hot tub was not working but didn’t really need it Staff was very nice especially Hailey at the front desk . We were very happy and would definitely go back"
A verified traveler stayed at Chesapeake Beach Resort
Posted 1 day ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
More Hotel Options in Islamorada
- Adults Only Resorts & Hotels in Islamorada
- Adventure Hotels in Islamorada
- Beach Hotels in Islamorada
- Boutique Hotels in Islamorada
- Business Hotels in Islamorada
- Cheap Hotels in Islamorada
- Family Hotels in Islamorada
- Golf Hotels in Islamorada
- Green Hotels in Islamorada
- Historic Hotels in Islamorada
- Hotel Wedding Venues in Islamorada
- Hotel with a Concierge in Islamorada
- Hotels with Bars in Islamorada
- Hotels with Early Check-in in Islamorada
- Hotels with Free Parking in Islamorada
- Hotels with Hot Tubs in Islamorada
- Hotels with WiFi in Islamorada
- Hotels with a Pool in Islamorada
- Hotels with smoking rooms in Islamorada
- Luxury Hotels in Islamorada
- Pet-friendly Hotels in Islamorada
- Resorts & Hotels with Spas in Islamorada
- Scuba Diving in Islamorada
- Shopping Hotels in Islamorada
More Accommodation Types in Islamorada
- Vacation Homes in Florida
- Condo Rentals in Florida
- Apartments in Florida
- Villas in Florida
- Cottages in Florida
- Resorts in Florida
- Aparthotels in Florida
- Motels in Florida
- Guest Houses in Florida
- Cabin Rentals in Florida
- B&B in Florida
- Houseboats in Florida
- Town Houses in Florida
- RV Parks in Florida
- Farmstay in Florida
- Condo Resorts in Florida
- Lodges in Florida
- Hostels in Florida
- Chalets in Florida
- Residences in Florida
- Holiday Park Resorts in Florida
- Inns in Florida
- Country Houses in Florida
Hotels near popular Islamorada Attractions
- Hotels near Anne's Beach
- Hotels near Bud n' Mary's Dive Center
- Hotels near Founders Park
- Hotels near Florida Keys Brewing Co.
- Hotels near Islamorada County Park
- Hotels near Windley Key Fossil Reef Geological State Park
- Hotels near Sunset Drive Beach
- Hotels near Robbie’s of Islamorada
- Hotels near History of Diving Museum
- Hotels near Islamorada Brewery & Distillery
Islamorada Hotels by Star Rating
Explore more hotels
- Breezy Palms Resort
- The Islands of Islamorada
- Sunset Inn
- La Jolla Resort
- Treasure Harbor
- Drop Anchor
- Pines & Palms Resort
- Ragged Edge Resort & Marina
- Sands of Islamorada
- Islander Bayside Villas and Boatslips
- Casa Morada
- The Caribbean Resort
- Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
- OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
- Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25
- The Ocean View Inn & Pub
- Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
- WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
- Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
- Beach Residence / Private overwater dock / Heated Pool / Mahi Key