Islamorada Holiday Rentals

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Holiday Rentals in Islamorada

Exterior
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very good, (315)
"Great view and you can fish right on the property "
The price is NZ$321
per night
16 May - 17 May
Breezy Palms Resort
Property grounds
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
10.0 out of 10, Exceptional, (1)
"Very hood stay"
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
Property grounds
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
9.6 out of 10, Exceptional, (71)
"The Irvine’s are great hosts, and we had a wonderful week. This house is a great location for boaters, with easy access to both the gulf and Atlantic. We will look forward to another stay."
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
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2 outdoor pools, open 8:00 AM to 6:00 PM, pool 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
Southern Diversion Estate Islamorada see our winter discounts
10.0 out of 10, Exceptional, (62)
"We had a wonderful family stay. Jon, the property manager was very helpful during check in! We loved the location, so close to grocery shopping and restaurants. We spent a lot of our time at the house , enjoying the gorgeous outdoor areas. The water was beautiful! We were six adults and six younger children. It was really nice to have so much room for everyone! The beds and linens were very comfortable, always important to us! We had a great time and will be visiting again!"
Southern Diversion Estate Islamorada see our winter discounts
On the beach, sun-loungers, beach towels
Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
10.0 out of 10, Exceptional, (64)
"Loved the property and had a great time but the luxury in the listing was not there. The biggest issue being the pergola in the pictures was gone and replaced with a single umbrella. The string lights in the backyard were broken and the majority of items were powered by extension cords laying on the ground, many with tripped breakers. The pool/hot tub was unable to be controlled and we needed to text someone whenever we wanted a change. The outdoor cinema experience was a projector in a box that...
Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
Beach
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
9.8 out of 10, Exceptional, (13)
"Me and 2 buddies stayed here while we went fishing. The place is a good place to stay with friends or family. 3 bedrooms and close to the pool and beach."
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
A heated pool
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
9.8 out of 10, Exceptional, (140)
"We really enjoyed our time at this villa! Owners were super accommodating and loved the location!"
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
Terrace/patio
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
8.0 out of 10, Very good, (7)
"Stressful upon arrival as we had not yet received our access code. It took 40 minutes to finally reach someone at Vacasa’s to assist us. The patio door screens were both off the track leaning against the outdoor wall. 2 kitchen light bulbs were burnt out. The queen mattress had stains in both sides. The bottom of our feet were dirty from walking on the tile floor. Clear lay not cleaned properly patio furniture had oversized cushions that didn’t fit the furniture properly"
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
Aerial view
House in Islamorada, in exclusive Venetian Shores.
House in Islamorada, in exclusive Venetian Shores.
Pool
Penthouse Paradise | Developer Unit w/ Every ★ Upgrade Possible!!
10.0 out of 10, Exceptional, (6)
"Perfect for a getaway weekend in paradise"
Penthouse Paradise | Developer Unit w/ Every ★ Upgrade Possible!!
Outdoor pool, a heated pool
Oceanfront, Spacious Gourmet Kitchen, Includes 31' Boat Slip, Dock, Pool & Beach
10.0 out of 10, Exceptional, (18)
"Exceeded all expectations"
Oceanfront, Spacious Gourmet Kitchen, Includes 31' Boat Slip, Dock, Pool & Beach
Pool
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more
10.0 out of 10, Exceptional, (75)
"Property was beautiful and bungalow super comfy and clean. We decided last minute to drive down to Islamorada with our 2 small dogs for our anniversary, and Miranda made everything flow so smoothly, I could not ask for more. Thank you for sharing your lovely home with us. Everything was absolutely perfect."
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more
Exterior
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
10.0 out of 10, Exceptional, (8)
"Beautiful, spotlessly clean, comfortable, well appointed, great pool! A lovely little cottage that had everything we needed! Perfect stay!"
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Pool
Private Beachfront Paradise
9.6 out of 10, Exceptional, (60)
"Beautiful property, incredibly private. The beach, deck, and outside areas were spectacular. We had three chicken friends that visited every day! We traveled to Marathon, Key West, and Tavernier while there, as well as Islamorada. Publix was right in town and we bought some groceries there, but also enjoyed many area restaurants. I think the listing should be updated as the beds were configured differently than we thought (2 bedrooms had 2 twin beds) and it worked for our family but might not...
Private Beachfront Paradise
On the beach
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
10.0 out of 10, Exceptional, (96)
"My family and I had a wonderful week at Angler's Reef. The house was absolutely beautiful, clean and very well kept. The kitchen was fully stocked which was great as we cooked several meals while visiting. The pool and grounds are well maintained, and the community has a safe, friendly vibe. We would highly recommend this home and Angler's Reef."
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
Property grounds
Superior 5bd Penthouse with gym, movie room, and private rooftop lounge
Superior 5bd Penthouse with gym, movie room, and private rooftop lounge
2 bedrooms, iron/ironing board, Internet, bed sheets
Charming oceanfront condo with pool, beach access, tennis, & washer/dryer
2.0 out of 10, (1)
"This was my fourth time in executive bay, But it was my first time using a vacation app. The amount of road noise and construction noise turned a well planned vacation into a bad experience! First impressions of the unit looked ok,until I noticed some of the cleaning that got overlooked. There were light fixtures that did not work or have bulbs but were left plugged in. There were also fixture that came on at will and switches that didn’t do anything.smoke alarms did not work and batteries were...
Charming oceanfront condo with pool, beach access, tennis, & washer/dryer
Pool
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
9.6 out of 10, Exceptional, (15)
"Location , staff , general area, cleanliness all were excellent. Loved our condo."
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
Outdoor pool, a heated pool
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
10.0 out of 10, Exceptional, (107)
"Great location and property. Would love to stay again in the future."
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
Don't see what you're looking for?
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.

Other types of properties in Islamorada you may be interested in

Private beach, sun-loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1004)
"Some staff were really good but in other areas, like the adult pool, the conditions and service were not good. "
The price is NZ$594
per night
13 Jun - 14 Jun
Cheeca Lodge & Spa
Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1320)
"Modern room, pools and hot tub. Hot tub wouldn’t turn on. Beach area nice to sit at."
The price is NZ$371
per night
16 May - 17 May
Chesapeake Beach Resort
Exterior
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1243)
"The resort was absolutely beautiful and the staff go above and beyond. The room key bracelets were so convenient and so cute to wear. We even got to keep them as souvenirs. Definitely the best place I have ever stayed. "
The price is NZ$526
per night
20 May - 21 May
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Islamorada holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Islamorada. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Islamorada. Seeing all the best attractions is bound to make you fall in love with Islamorada. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Islamorada short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Islamorada?

With 631 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Everglades National Park and Founders Park are a couple of scenic spots to enjoy the outdoors, whereas History of Diving Museum is one of the cultural attractions. 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.

Recent reviews of Islamorada properties
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