Find hotels in Islamorada, FL from $115

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May 16 - May 17
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May 17 - May 18
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May 17 - May 19
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Compare 2,122 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Private kitchen | Fridge, microwave, oven, stovetop
Villages at Hawks Cay Villa with Spa
10.0 out of 10, Exceptional, (199)
"Was a great relaxing stay"
Villages at Hawks Cay Villa with Spa
Towels
Waterfront villa with 5 kayaks, covered deck, washer/dryer, & AC
9.8 out of 10, Exceptional, (8)
"Excellent location if you're looking for safe, quiet, very clean complex. Everyone was very nice. Our unit was very nice and the back patio so relaxing. Would definitely recommend!"
Waterfront villa with 5 kayaks, covered deck, washer/dryer, & AC
Outdoor pool
Palm Villa May dates available
9.8 out of 10, Exceptional, (123)
"The owners are 5 star! The villa is conveniently located to the main Hawks Cay lodge as well as the Angler & Ale Restaurant and docks. The unit is clean, comfortable and accommodates 4 adults with everything you need for a relaxing, fun filled getaway. If you plan ahead, like we always do when coming to the Keys, I suggest you stop at Publix and stock up on any food, drinks and extras (shampoo, laundry detergent, dishwasher tabs, etc) that you may want while on property as it’s about a 25 min...
Palm Villa May dates available
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Beach
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
9.8 out of 10, Exceptional, (42)
"Love Duck Key!"
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
Property grounds
Villa 5054 on Duck Key BOAT SLIP available
9.8 out of 10, Exceptional, (36)
"My husband and I traveled with our son (6) for our first Keys trip the first week of April. The rental was comfortable with a full kitchen for our own cooking and everything was clean. The view is perfection and the deck is steps away from the water. We were able to fish and enjoy the beautiful sunsets right outside the place. The location is quiet enough with alot of families but close to shops and restaurants. We will definitely be back and Frank was easy to contact. Great adventure!"
The price is $219
$560 total
includes taxes & fees
May 20 - May 21
Villa 5054 on Duck Key BOAT SLIP available
Property grounds
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
9.8 out of 10, Exceptional, (55)
"Enjoyed the location everyone at this location was very friendly, the views and sunrises were beautiful. The unit could use a new mattress but enjoyed the stay."
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
The Islands of Islamorada
4.0 star property
9.6 out of 10, Exceptional, (35)
"My wife and I have been traveling to Islandmorada for many years and this place is what we have been searching for. Clean, quaint, all the amenities of a large restort withiut the corporation feel. Absolutely refreshing!"
The Islands of Islamorada
Pool
2-BEDROOM 3 BATH 299nt + Pool on BLUE LAGOON. SLEEPS 6
9.6 out of 10, Exceptional, (32)
"Great property, excellent location, very well maintained. Enjoyed our stay, Marc was very easy to work with, excellent communication and very responsive. My only criticism is the bathrooms are a bit small, but everything else was perfect."
2-BEDROOM 3 BATH 299nt + Pool on BLUE LAGOON. SLEEPS 6
Exterior
Grassy Flats Resort & Beach Club
2.5 star property
9.4 out of 10, Exceptional, (160)
"Super friendly and helpful staff. Great location for just chilling out. Green - refill water bottles provided. Our double aspect room in the adult only part of the hotel was stunning and had the quietest air-con that didn't disturb my sleep - the refrigerator still rumbled away in the night but was quietest of all the others on our road trip!! (not used to air con or a refrigerator in the bedroom at home!!)"
The price is $285
$321 total
includes taxes & fees
May 29 - May 30
Grassy Flats Resort & Beach Club
Property grounds
Casa Morada
3.5 star property
9.4 out of 10, Exceptional, (351)
"Loved our stay! Unique property, we will be back again! Thank you!"
The price is $300
$414 total
includes taxes & fees
May 27 - May 28
Casa Morada
Flat-screen TV
Treasure Harbor
2.0 star property
9.4 out of 10, Exceptional, (28)
"The houseboat was adorable. It was probably one of the cleanest “hotels” I’ve ever stayed at. The area was very quiet and peaceful. Loved watching the dolphins from the deck in the morning. The front desk staff were wonderful- very friendly. There was an excellent bagel place a short walk away. The only thing to keep in mind is the boat says it sleeps 7 but the 7th loft bed would really only work for a child- or very small agile adult. Not a complaint (we were a group of 6) just something to...
The price is $181
$329 total
includes taxes & fees
May 20 - May 21
Treasure Harbor
Fridge, microwave, oven, stovetop
Villa 5023 on Duck Key BOAT SLIP available
9.4 out of 10, Exceptional, (25)
"This unit was spotless and laid out in a very efficient way. The views from the back porch and upper porch off the bedroom are gorgeous, especially for sunsets. The stairs to the bedrooms on the upper level are high however, for people that have trouble with stairs, it could be difficult. We loved the cleanliness and the location, which was close to Marathon and restaurants."
The price is $219
$560 total
includes taxes & fees
May 20 - May 21
Villa 5023 on Duck Key BOAT SLIP available
Outdoor pool, a heated pool, pool umbrellas, sun loungers
Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (955)
"Beautiful place to get away with your family"
The price is $156
$224 total
includes taxes & fees
Jun 2 - Jun 3
Pines & Palms Resort
Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1005)
"Beautiful property. Love the updates. Staff friendly. had a wonderful stay. "
The price is $329
$432 total
includes taxes & fees
Jun 16 - Jun 17
Cheeca Lodge & Spa
3 outdoor pools, cabanas (surcharge), pool umbrellas
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1003)
"We had a lovely stay at the resort. Staff were pleasant and friendly. The rooms were clean and nicely decorated. The two pool areas were beautiful along with the beach area. Our family had fun riding the bikes every day. We even got to witness a sea turtle release on the premises. The only draw back for me was the matter of lots of smoking. We had a non smoking room but the people next to us smoked on the patio outside causing our patio area to become engulfed with smoke as well as our room...
The price is $239
$324 total
includes taxes & fees
May 23 - May 24
Islander Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Good"
The price is $186
$244 total
includes taxes & fees
May 19 - May 20
Drop Anchor
Outdoor pool, pool umbrellas, sun loungers
Islander Bayside Villas and Boatslips
3.5 star property
9.0 out of 10, Wonderful, (335)
"Lovely sister property to the Islander - Resort; the, Islander Bayside resort Townhomes are wonderful. The Green Tuttle Inn. And the NEST across overseas highway great spirits & food. kitchens open until 10pm. 7 am green turtle breakfast. Or Mangrove Mike’s is a short walk North for breakfast. First night we walked to Lorelei, (15 minutes walk) for sunset. Best spot. This property is Slightly less than 2 miles NORTH from Bud and Mary’s marina and Lazy Days. Ideal for family or larger...
The price is $287
$378 total
includes taxes & fees
May 27 - May 28
Islander Bayside Villas and Boatslips
View from property
La Jolla Resort
2.5 star property
8.8 out of 10, Excellent, (893)
"Nice room. Loved the dock and pool area. "
The price is $149
$167 total
includes taxes & fees
May 21 - May 22
La Jolla Resort
Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio
Sands of Islamorada
2.5 star property
8.8 out of 10, Excellent, (324)
"Super Clean rooms, nice staff, TV was basic, easy on -off highway. Nice restaurants within walking distance. "
The price is $162
$182 total
includes taxes & fees
May 20 - May 21
Sands of Islamorada
View from property
Edgewater Lodge
2.5 star property
8.6 out of 10, Excellent, (710)
"This was my 4th stay at the hotel. I gave this location a 5 star, it has everything I needed for a bae cation. Quiet and peaceful. If you need to get away for the world this is the perfect spot. No complaints hear 💕💕💕 Edgewater lodge"
The price is $269
$303 total
includes taxes & fees
May 19 - May 20
Edgewater Lodge
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See all available properties in Islamorada
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.

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Islamorada showing a beach bar

Matecumbe

6 out of top 10 points of interest in this area

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Anne's Beach are top sights worth seeing.

Find hotels in Matecumbe

More cheap stays in Islamorada

Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL
The price is $199 per night from May 19 to May 20
$199
per night
May 19 - May 20
8.8/10 Excellent! (1,317 reviews)

Stay near popular Islamorada attractions

Image for Theater of the Sea

Theater of the Sea

4.5/5(215 reviews)

Swim with the dolphins and sharks and feed the crocodiles and sea turtles near the lagoon of this vast interactive park for marine mammals.

See properties
Theater of the Sea

Islamorada Travel Info

Number of reviews
5,476
Accommodation
2,122 hotels
Highest price
$329
Lowest price
$115
Reasons to visit
Theater of the Sea, Annes Beach and Windley Key Fossil Reef Geological State Park
Hotels with entertainment
36
Hotels with nearby beaches
23

Price trends for hotels in Islamorada

Less expensive
More expensive
Next month
October
March
$266
Month
Price
January
$320
February
$404
March
$422
April
$344
May
$248
June
$266
July
$285
August
$264
September
$216
October
$207
November
$255
December
$347
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Islamorada. Select dates and complete search for nightly totals inclusive of taxes and fees.

Frequently asked questions

Where is the best place for a stay in Islamorada?

The Caribbean Resort is ranked highly by Expedia customers. This hotel offers a marina and an outdoor pool. Other top choices based on traveler reviews include Treasure Harbor and Sunset Inn. See all available top hotels, or vacation rentals in Islamorada.

What are some of the best vacation home rentals in Islamorada?

Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip: Visitors like this Islamorada vacation home rental. It is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind. See all vacation rentals in Islamorada.

If I need to cancel my hotel reservation in Islamorada, will I receive a refund?

Yes! You'll find that most hotel reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Islamorada.

Where can I learn more about changing or cancelling my trip to Islamorada?

For more details about picking new dates or cancelling your trip to Islamorada, click here.

What's the best budget-friendly accommodation in Islamorada?

Based on reviews, Chesapeake Beach Resort is a popular hotel for our travelers who want a more economical choice, and features 2 outdoor pools and air conditioning. View all budget hotels in Islamorada.

What's the best place to stay for a family vacation to Islamorada?

Cheeca Lodge & Spa is a resort with 3 outdoor pools and a private beach, and it's a top choice on Expedia for families. Other good options for your family trip include Amara Cay Resort and Islander Bayside Villas and Boatslips. Attractions in the area like John Pennekamp Coral Reef State Park and Jacob's Aquatic Center are also fun for kids of all ages. Find more child-friendly accommodations in Islamorada.

What's the best place to stay for a couple going to Islamorada?

Cheeca Lodge & Spa is a favorite resort for couples, and features a full-service spa and a private beach. Other good choices for your romantic getaway include La Siesta Resort & Villas and Amara Cay Resort. See all romantic hotels in Islamorada.

What's the best pet-friendly place to stay in Islamorada?

Chesapeake Beach Resort is a top hotel for people traveling with their pets, and offers 2 outdoor pools and pillowtop beds for its human guests. Other good options for you and your pet include La Siesta Resort & Villas and Amara Cay Resort. See more pet-friendly hotel accommodations in Islamorada.

Where is the best place to stay close to Florida Keys Brewing Co.?

One of the top choices for your stay is Cheeca Lodge & Spa, located next to Florida Keys Brewing Co., and this 4-star resort offers 3 outdoor pools and a full-service spa. Islander Resort and Islander Bayside Villas and Boatslips are a couple of other good options close by.

What about the best place to stay close to Bud n' Mary's Dive Center?

One of the top choices for your stay is Amara Cay Resort, located next to Bud n' Mary's Dive Center, and this 3.5-star hotel offers a private beach and 2 restaurants. La Siesta Resort & Marina and Pines & Palms Resort are a couple of other good and close options.

What's the best place to stay near the beach in Islamorada?

Chesapeake Beach Resort is a top hotel located on the beach. Other good options to stay near the beach include Cheeca Lodge & Spa and La Siesta Resort & Villas. See more stays near the beach in Islamorada.

What's the best high-end place to stay in Islamorada?

Cheeca Lodge & Spa is a 4-star resort with a private beach and 3 restaurants, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Find more luxury hotels in Islamorada.

Recent reviews of Islamorada hotels
Expedia verified reviews

Islander Resort

Islander Resort

5/5 Excellent
"We had a lovely stay at the resort. Staff were pleasant and friendly. The rooms were clean and nicely decorated. The two pool areas were beautiful along with the beach area. Our family had fun riding the bikes every day. We even got to witness a sea turtle release on the premises. The only draw back for me was the matter of lots of smoking. We had a non smoking room but the people next to us smoked on the patio outside causing our patio area to become engulfed with smoke as well as our room whenever we opened the door. People also smoked at the pool area and the outdoor bar/restaurant area. I understand these are all outdoor areas however if you are a non smoker it really is unpleasant to endure smoke while you are eating or relaxing. "
A verified traveler stayed at Islander Resort
Posted 6 hours ago
Islander Resort