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Top Holiday Rentals in Islamorada

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
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
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4 bedrooms, desk, iron/ironing board, free WiFi
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 | Outdoor pool, a heated 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
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!!
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 | Outdoor pool, a heated pool
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
10.0 out of 10, Exceptional, (6)
"Great Property, Awesome Location, Very Reasonably Priced, Super Nice Owner…wish we could have stayed longer. We arrived Friday afternoon after spending the morning in Everglades Safari Parl and stopping by Alabama Jacks for lunch in Key Largo. We unpacked, checked things out (including the pool) before heading over to Robbie’s for an amazing sunset catamaran cruise …checked out the old lighthouse, saw dolphins and the most amazing sunset and beautiful water that I’ve typically only seen in the...
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Beach nearby, sun-loungers, beach towels
Peacock Shores Islamorada - Vacation On The Beach!
10.0 out of 10, Exceptional, (25)
"Such a serene location and beautiful well appointed home. We loved everything about it!"
Peacock Shores Islamorada - Vacation On The Beach!
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
Lake
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
10.0 out of 10, Exceptional, (58)
"Very nice, spacious, well-provisioned house with some water view from the back deck. Great central pool, and a good dock you can rent for a reasonable rate if you're renting a boat. Cute neighborhood, central to tons of restaurants and amazing activities. Rob & Jen were very communicative hosts who responded to every request within an hour."
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
Aerial view
💎AQUAMARINE💎<-WALL 2 WALL-> OCEAN-VIEW🌊+DOCK+POOL+SPA+GYM+🎾+DEALS ⭐️⭐️⭐️⭐️⭐️
10.0 out of 10, Exceptional, (134)
"This property was the start of our 2 week break in Florida, what a fantastic place to stay. Great position to wake up to the sunrise and then take the boat out later in the day to see the sunset. Communication throughout was excellent and it seemed as if we had the place to ourselves, the community areas were very quiet."
💎AQUAMARINE💎<-WALL 2 WALL-> OCEAN-VIEW🌊+DOCK+POOL+SPA+GYM+🎾+DEALS ⭐️⭐️⭐️⭐️⭐️
Beach | On the beach, beach towels
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, (141)
"We are so grateful we got to experience this beautiful property. The whole community is well maintained and immaculate. It’s a very quiet and peaceful neighborhood but still close to stores, restaurants and outdoor activities. The condo is also well maintained and spotless. The decor is warm and welcoming. I especially appreciated the high quality towels and linens. The kitchen is well equipped, we especially enjoyed having the grill ( again very clean). My only suggestion would be is to have...
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
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!
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 | Outdoor 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
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."
The price is €280
includes taxes & fees
21 May - 22 May
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
On the beach
Relaxing waterfront retreat with boat dock & amazing ocean views
9.4 out of 10, Exceptional, (3)
"house needs updating"
Relaxing waterfront retreat with boat dock & amazing ocean views
Exterior
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very good, (320)
"Very good value. Clean if a little run down and wonderful location and staff. "
The price is €161
includes taxes & fees
20 May - 21 May
Breezy Palms Resort
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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.

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, (1006)
"Beautiful property. Love the updates. Staff friendly. had a wonderful stay. "
The price is €470
includes taxes & fees
16 Jun - 17 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, (1324)
"Nicely renovated resort unfortunately water in the swimming pool was very hot (impossible to stay in the water for more than 10 minutes). Great beach area but water very shallow with a rocky bottom."
The price is €253
includes taxes & fees
21 May - 22 May
Chesapeake Beach Resort
3 outdoor pools, pool cabanas (surcharge), pool umbrellas
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1004)
"Beautiful remodel on the property "
The price is €298
includes taxes & fees
30 May - 31 May
Islander 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.

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
Expedia verified reviews

Breezy Palms Resort

Breezy Palms Resort

5/5 Excellent
"Very good value. Clean if a little run down and wonderful location and staff. "
A verified traveller stayed at Breezy Palms Resort
Posted 2 days ago
Breezy Palms Resort