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Featured Islamorada Hotels with Bars

See all 338 Hotels in Islamorada
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy, Islamorada
4.0 out of 5.0
4.3 out of 5 (1,201 reviews)
awesome placeeverything looks new condition, very clean, ac very cold.
  Sep 5, 2017

$219

$219
Islander Resort

Islander Resort

82100 Overseas Highway, Islamorada
3.5 out of 5.0
4.2 out of 5 (1,745 reviews)
No clean towels for the second day, internet not good. No paper towel either.
  Sep 9, 2017
Postcard Inn Beach Resort & Marina

Postcard Inn Beach Resort & Marina

84001 Overseas Hwy, Islamorada
3.5 out of 5.0
3.8 out of 5 (1,198 reviews)
very nice hotel with beautiful beachwell we only stayed for one night due to hurricane Irma. we only had time to enjoy the very nice beach. the only downfall for me was not being able to smoke outside. I understand people don't like it, but its outside so what does it matter. otherwise this a beautiful property.
  Sep 11, 2017
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Islamorada
4.5 out of 5.0
4.4 out of 5 (1,433 reviews)
Daughter got married here on the beach at sunset. Beautiful hotel and spa facilities. Close enough to Miami in terms of travel, but you feel like you're away in the Caribbean.
  Sep 11, 2017
Pelican Cove Resort & Marina

Pelican Cove Resort & Marina

84457 Overseas Highway, Islamorada
3.5 out of 5.0
3.9 out of 5 (1,083 reviews)
Wonderful hotel! The staff was so friendly, the rooms were nice and clean! Great staff and amenities
  Sep 5, 2017
Smuggler's Cove Resort and Marina

Smuggler's Cove Resort and Marina

85500 Overseas Highway, Islamorada
3.0 out of 5.0
3.0 out of 5 (184 reviews)
Nice motel on MarinaBar & restaurant on premises.very comfortable stay.
  Mar 24, 2017

$129

$129
Pines & Palms Resort

Pines & Palms Resort

80401 Old Hwy, Islamorada
3.5 out of 5.0
4.4 out of 5 (345 reviews)
A nice old florida cottage. Typical of the keys. Nice people.
  Nov 19, 2017

$119

$119
Casa Morada

Casa Morada

136 Madeira Road, Islamorada
4.0 out of 5.0
4.7 out of 5 (44 reviews)
A very special placeNever imagine that it would be so great. I made the reservation without even looking at the pictures. I will go back as much as i can.
  Dec 5, 2017

$379

$379
Lime Tree Bay Resort

Lime Tree Bay Resort

68500 Overseas Hwy, Long Key
4.0 out of 5.0
4.1 out of 5 (527 reviews)
Super nice staffSuper nice people very helpful . !!!!!!!!!!!!!!!! ...........................
  Dec 18, 2017

$116

$116
Creekside Inn Islamorada

Creekside Inn Islamorada

90611 Old Highway, Islamorada
2.5 out of 5.0
3.5 out of 5 (650 reviews)
Great hotel and location Was a great experience. They have done a great job in renovating the rooms. Everything was clean and nice. We only had ONE complaint- there are no curtains on the windows (only shades), therefore all the light came in at night.
  Dec 2, 2017

$125

$125
La Siesta Resort & Marina

La Siesta Resort & Marina

80241 Overseas Highway, Islamorada
3.5 out of 5.0
3.8 out of 5 (639 reviews)
Awesome hotelThe hotel was amazing, only bad the breakfast very poor but the rest of amenities perfect.
  Sep 5, 2017
Harbor Lights

Harbor Lights

84951 Overseas Hwy, Islamorada
2.5 out of 5.0
2.9 out of 5 (855 reviews)
Quiet place, close to the beach and other facilit.Small place, nice and very helpful lady in front desk. A few minutes from the Theater of the sea, good food around too.
  Jul 26, 2017
Fiesta Key RV Resort

Fiesta Key RV Resort

70001 Overseas Hwy, Long Key
3.0 out of 5.0
3.1 out of 5 (226 reviews)
Family friendly Rooms were nice and conviently close to the pool and restaurant. The room was a little out dated but it still was clean and worked for us
  May 17, 2017
Drop Anchor Resort and Marina

Drop Anchor Resort and Marina

84959 Overseas Highway, 222, Islamorada
3.5 out of 5.0
4.2 out of 5 (814 reviews)
Great hotel and incredible locationI was not expecting what we ended up with! When checking in the staff was most helpful and the room was so clean! Set your expectations for a Key style older resort that has been renovated with care and pride of ownership shows throughout the grounds. This is a place I will definitely come back to. ...
  Dec 16, 2017

$169

$169
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada
3.0 out of 5.0
3.9 out of 5 (535 reviews)
Nice hotel on waterWell we loved every second of our trip didnt even have to leave the hotel to have fun spent 3 days here and the fishing and snorkeling was our main goal and it was absolutely perfect the hotel in my eyes is outdated but the keys is an old fishing town so i expected it to stay that way no complaints ...
  Aug 25, 2017
The Caribbean Resort

The Caribbean Resort

117 Carroll St, Islamorada
4.0 out of 5.0
4.9 out of 5 (47 reviews)
Great Family Vacation!Spent a long weekend with our family and stayed in the Harbor House. Beautifully decorated and appointed. Two bedrooms and a pull out sleeps 6 comfortably. Great location and amenities. I highly recommend them. If you like the décor...go to their shop, Ocean Gardens. We found quite a few items that ...
  Aug 23, 2017
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

84801 Overseas Highway, Islamorada
2.5 out of 5.0
3.4 out of 5 (164 reviews)
Nice older near the water. 22 night stay. Only there at site mainly in evening. Quiet and pretty. Beautiful sunrises!
  Feb 3, 2017

$215

$215
Breezy Palms Resort

Breezy Palms Resort

80015 Overseas Highway, Islamorada
3.0 out of 5.0
3.8 out of 5 (18 reviews)
Nice hotel when you have a boat. Laughable beachVery Nice and helpful staff, Dive store just across chainlink fence. Beach muddy and shallow. Maybe 60 ft wide. Prime spot for divers and boaters. Has own marina and boat ramp.
  Aug 23, 2017

$186

$186
Lookout Lodge Resort

Lookout Lodge Resort

87770 Overseas Hwy, Islamorada
3.0 out of 5.0
3.8 out of 5 (76 reviews)
Rundown but Great LocationI have stayed here before, the views and location are amazing. The Staff is exceptional, but the rooms are in dire need of repair and upgrade. I was not thrilled to find out upon check in that the bulk of the property had been reserved for a Private Party on the day of my arrival and would be closed. ...
  Jul 4, 2017
Bayside Townhomes and Boatslips

Bayside Townhomes and Boatslips

81450 Overseas Highway, Islamorada
4.0 out of 5.0
4.6 out of 5 (160 reviews)
Usually stay at the cheeca Just as nice without the restaurant and tiki bar
  Oct 27, 2017
Map

Recently booked Hotels with Bars in Islamorada

Lime Tree Bay Resort
4.0 out of 5.0
Last booking: 1 hour ago
Amara Cay Resort
4.0 out of 5.0
Last booking: 3 hours ago
Casa Thorn
3.0 out of 5.0
Last booking: 8 hours ago
Casa Morada
4.0 out of 5.0
Last booking: 8 hours ago
Conch On Inn Motel
2.0 out of 5.0
Last booking: 15 hours ago
Drop Anchor Resort and Marina
3.5 out of 5.0
Last booking: 16 hours ago
Creekside Inn Islamorada
2.5 out of 5.0
Last booking: 32 hours ago
Smuggler's Cove Resort and Marina
3.0 out of 5.0
Last booking: 33 hours ago
Pines & Palms Resort
3.5 out of 5.0
Last booking: 38 hours ago

Like a classic mixed drink, your perfect vacation must have just the right combination of ingredients. If you are seeking the ideal base for a wonderful trip then search no further than Islamorada. Something big must be happening in Islamorada to have travelers double this past year. Now that you narrowed down the location, the next step is to add the finishing touches for a vacation you'll want a second round of.

Make Your Vacation to Islamorada Shaken and Stirred

If you want a spot that is the go-to spot, then you have come looking in the right place. These hotels don't only offer you a place to rest your head at night, but also act as the heartbeat of Islamorada. Staying at one of these hotels can be a one-stop shop for your trip. No matter how inviting the barrooms at these hotels are, you can't stay in them overnight. Luckily, a stay in Islamorada bar hotels typically supplies:

  • A staff that assures you have clean linens, apt service, and that the small items are taken care of
  • A staff that takes the time to tidy up your room and make the bed each day during your visit, so when you return it seems as if you've just arrived
  • Exercise room, hot tub, updated lobby, and grounds that are well-maintained
  • Rooms furnished with comfortable chairs, premium bedding, and luxurious sheets, your continued comfort is a top concern for these hotels

With a hotel that's so nice from barstool to bedroom, you may never be required to depart.

Book Your Islamorada Hotel Today!

Don't think too long about sipping an ice-cold blended cocktail or you may miss your chance to pull up to one of these hotel bars. Book your hotel with a top-shelf lounge in Islamorada soon, because everyone else is also. Your vacation should be the perfect blend of excitement and relaxation, and Expedia has hotel lounges on tap that can provide that winning combination.