Holiday Rentals in Islamorada

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Holiday Rentals in Islamorada

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (421)
"We visited Breezy Palms for our 20th wedding anniversary. We took advantage of the boat rental on site, had a great day on the water. Played cards on our lanai. Used the lovely pool, walked to local restaurants, and had a memorable time. Definitely will be back!"
The price is €209
includes taxes & fees
6 Apr - 7 Apr
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Everything was lovely except I felt rushed on my departure date. A front desk representative knocked around 9am to find out what time I was leaving. If your check out policy is 11am, you should not knock on people’s door to find out what time they are planning on leaving. It doesn’t feel like a luxurious experience when you do. In addition to the early knock, the entire housekeeping staff was waiting by my front door when I checked out at 10:25. What if I wasn’t checking out at 10:25 and was...
The price is €652
includes taxes & fees
6 Apr - 7 Apr
The Islands of Islamorada

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (77)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

9.8 out of 10, Exceptional, (79)
"Three generations of our family enjoyed a wonderful vacation at The Last Resort. The house was beautifully appointed and well stocked as described in the listing. It had everything we needed for a memorable beach vacation. The owner was friendly, helpful, and easy to communicate with. We hope to return! back!ThownerfrieThowwith. "
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

10.0 out of 10, Exceptional, (174)
"We've visited Angler's Reef many times over the years and haven't been let down yet. First time in Linda's & Roger's home. It is a very nice home; furnishings nice, appliances all work, home was just as described. Owners were easy to communicate with; converted twins to King and arranged dock access for us in advance. I'd highly recommend to anyone. "
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

Private Beachfront Paradise

9.6 out of 10, Exceptional, (65)
"Good location "
Private Beachfront Paradise

TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

10.0 out of 10, Exceptional, (86)
"This was our first time visiting the keys and we found the perfect place. It was everything and more than described and offered a central place to explore the Florida Keys. Our host was very good at keeping us informed and answer questions throughout the week. The bungalow was perfect inside and out along with an amazing pool just steps from our door. "
The price is €1,130
includes taxes & fees
31 Mar - 1 Apr
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (17)
"This cluster of cottages is a small “community” within a neighborhood off Highway 1 in the Keys. Very close to things you need like restaurants, grocery and close enough to beachy areas like Sombrero Beach on Marathon or Bahia Honda a bit farther south. Loved the quiet pool and our fire pit for those cooler January nights. The neighbors seemed to be a mix of permanent residents, boaters, renters and snowbirds. This is ideal for couples and maybe kids who don’t mind sharing a small double (full)...
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Gorgeous Ocean Views, Ground Floor Studio

10.0 out of 10, Exceptional, (6)
"Nice cozy place for a couples getaway. Awesome pool and oceanfront views. Many good restaurants with outside seating close by. "
Gorgeous Ocean Views, Ground Floor Studio

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

8.6 out of 10, Excellent, (10)
"Overall the property was nice. Very quaint. A previous review mentioned how small the bathroom was. I agree, but for us it wasn't a huge ordeal. I would say it made it challenging when trying to get ready because the sink takes up all the counter space. Luckily there is a wall shelf in the kitchen that we utilized. Would be nice to have mirrors in the bedrooms, and maybe some shelving in the bathroom to set items on during the stay. Our front door seemed to lack the shades that the other...
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (51)
"Clean nice area great place"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Peacock Shores Islamorada - Vacation On The Beach!

10.0 out of 10, Exceptional, (32)
"Can’t say enough about this place or the host! Everything you read about it is absolutely true. Wouldn’t change a thing. Thank you, Mike, for sharing your little piece of paradise!"
Peacock Shores Islamorada - Vacation On The Beach!

Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool

10.0 out of 10, Exceptional, (44)
"My family really enjoyed our stay for two weeks in Angler's Reef. We loved how there was room for everyone. The community where the home was nice and private. The kids enjoyed the pool and easy acces to the beach. The pool was heated which made it nice going into. There was plenty of food options nearby. We will definitely come back when we visit the keys again. "
Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool

RELAX in your PRIVATE Oceanfront Cottage!

10.0 out of 10, Exceptional, (103)
"Our third time staying here was as wonderful as the first two. So peaceful and comfortable. All the comforts of home, close to grocery, restaurants and pharmacy if needed. It’s just the best place to stay when escaping the northern states for a little warmth and sunshine in mid winter. I can’t imagine staying anywhere else in the Keys.This place is our favorite of favorites!"
RELAX in your PRIVATE Oceanfront Cottage!

AQUAMARINE OCEANVIEW “”FLASH SALE 4/5-4/12/2025”””FREE DOCK+POOL+GYM+149 REVIEWS

10.0 out of 10, Exceptional, (149)
"Great location—quiet but close to everything. Loved having a dock right out the back door. Will definitely be back"
AQUAMARINE OCEANVIEW “”FLASH SALE 4/5-4/12/2025”””FREE DOCK+POOL+GYM+149 REVIEWS

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

10.0 out of 10, Exceptional, (108)
"Lovely condo and property "
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

10.0 out of 10, Exceptional, (94)
"The perfect place for our three generation family vacation! The property is a setting of beautiful landcaping, gorgeous sunrises, and a variety of wildlife. The indoor and outdoor amenities are plentiful, including a pool, fire pit, cabanas, outdoor seating areas, plus a very clean, inviting house. The dock supplied many hours of entertainment viewing manatees, barracudas, nurse sharks, and lobsters. The host was very available to answer questions. "
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Islamorada Boaters Paradise with 70' Dock and private beach access..

10.0 out of 10, Exceptional, (19)
"Everything was amazing for our stay. We were able to have the boat right at the house for easy access for sunset boat rides and our everyday fishing adventures. "
Islamorada Boaters Paradise with 70' Dock and private beach access..

Disc Apr-Jun2025 -Exec Bay w/Heated Pool, Marina, Beach, Dogs ok, Tennis/Pickleball

9.4 out of 10, Exceptional, (16)
"As advertised "
Disc Apr-Jun2025 -Exec Bay w/Heated Pool, Marina, Beach, Dogs ok, Tennis/Pickleball

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (106)
"My daughter got married in Islamorada (Destination wedding) and we needed a large home to accommodate family. This place was perfect. We had a boat and 2 jet skis and the dock accommodated all very easy. The house is well stocked and had paddle boards and sea kayaks. The young people loved them. We saw Manatees everyday at the dock, dolphins even came in one day. Beautiful home made for a grand wedding and vacation. Thank you!"
5 bedroom - Deep Dockage & Heated Pool 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.
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Other types of properties in Islamorada you may be interested in

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1046)
"Exceptional property, wonderful staff"
The price is €427
includes taxes & fees
9 Apr - 10 Apr
Cheeca Lodge & Spa

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1018)
"It would be nice to have music during the day Coffee availability would be a great idea as well Loved the property, the staff and convenience to other restaurants and shopping Highly recommend!!"
The price is €439
includes taxes & fees
6 Apr - 7 Apr
Islander Resort

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1225)
"Beautiful property with plenty of amenities. Very attentive staff. Thoughtfully laid out. "
The price is €403
includes taxes & fees
23 Mar - 24 Mar
Amara Cay Resort
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.

Frequently asked questions

Can I find a holiday rental in Islamorada?

Yes, there are holiday rentals close to the most popular sights in Islamorada, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Islamorada like the scenic seaside and entertainment choices this destination is known for. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Islamorada has to offer?

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!: This highly rated holiday home rental in Islamorada is located by the ocean, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Islamorada?

With 601 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Everglades National Park and Founders Park, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Bud n' Mary's Dive Center and Anne's Beach.

What’s a holiday rental in Islamorada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islamorada. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.