Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Breezy Palms Resort
Exterior
Breezy Palms Resort
2.5 star property
8.6 out of 10, Excellent, (371)
"Pictures and description are accurate. Clean rooms, comfortable beds, nice beach area and pool, though not resort like. Staff very pleasant and accommodating. No bar or food on site, but several walkable options. Boat jet ski rental available. Only downside was morning wake up by a wild rooster who calls the place his home."
The price is CA $155
CA $247 total
includes taxes & fees
Nov 24 - Nov 25
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (39)
"We loved the entire experiences; especially the amenities on site (kayaks, paddle boards, swimming-pool & ocean, food & bar) and Emmanuel (person responsible kayaks and paddle boards)."
The price is CA $889
CA $1,001 total
includes taxes & fees
Dec 2 - Dec 3
The Islands of Islamorada
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
Beach
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
10.0 out of 10, Exceptional, (4)
"Our family of 5 stayed here over Christmas and had a wonderful time. The house had everything we needed. We hope to return soon!"
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, and more
Outdoor pool, a heated pool
TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, and more
10.0 out of 10, Exceptional, (78)
"Our family of 5 had a great say here! All the details were exactly as expected. It's a charming house in a great location to explore all the Keys has to offer. We had a great trip in large part thanks to this property!"
TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, and more
💎AQUAMARINE OCEANVIEW⚡️FLASH SALE-OCT & DEC+”143”⭐️5 STAR REVIEWS+DOCK+POOL+GYM
Aerial view
💎AQUAMARINE OCEANVIEW⚡️FLASH SALE-OCT & DEC+”143”⭐️5 STAR REVIEWS+DOCK+POOL+GYM
10.0 out of 10, Exceptional, (143)
"Spent a week at this condo with 4 other adult family members. We all felt at home with plenty of space to just relax and hang out together. Fully equipped kitchen where one day we made broiled lobster tails bought directly across from the condo on the canal.We enjoyed looking at the sea and sky throughout the day with it's changing colors viewed from the glass wall in the great room. Our favorite was the teal blue of the sea; which is repeated in the furnishings of the condo. The condo is...
💎AQUAMARINE OCEANVIEW⚡️FLASH SALE-OCT & DEC+”143”⭐️5 STAR REVIEWS+DOCK+POOL+GYM
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
Pool
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
House in Islamorada, in exclusive Venetian Shores.
Aerial view
House in Islamorada, in exclusive Venetian Shores.
House in Islamorada, in exclusive Venetian Shores.
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Outdoor pool, a heated pool
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
10.0 out of 10, Exceptional, (14)
"Please note - the address is Overseas Highway, but to access the property, you have to go to Cortez Dr. Booked for 3 days to visit with family living in Islamorada. We were so pleased with the accommodations. Very clean, small, but plenty of space. Fire pit, swimming pool, washer/dryer, kitchen had everything needed to prepare meals (great for breakfast with grandkids), comfortable beds, nice shower, cold A/C (so cold you might need a throw blanket). One of the nicer rentals we have stayed...
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
On the beach, sun loungers, beach towels
Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
9.8 out of 10, Exceptional, (65)
"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
Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna
Property grounds
Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna
Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna
Penthouse Paradise Developer Unit with Every Upgrade Possible
Pool
Penthouse Paradise Developer Unit with Every Upgrade Possible
10.0 out of 10, Exceptional, (8)
"We enjoyed the well appointed rooms, outdoor deck & the unexpected outdoor loft looking out to the ocean. We also appreciated the additional amenities of paper towels, laundry detergent, dish & hand soap, toilet paper, trash bags, etc. which are not always provided at rentals. The covered parking, elevator & pool were nice features."
Penthouse Paradise Developer Unit with Every Upgrade Possible
Private Beachfront Paradise
Outdoor pool
Private Beachfront Paradise
9.8 out of 10, Exceptional, (61)
"Enjoyed our stay for my birthday celebration. Location was perfect - near shops and restaurants. Crib and high chair was great for grandson. Pool was wonderful - every day swimming! Weather was great until day we left - Hurricane Helene! "
Private Beachfront Paradise
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
A heated pool
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
10.0 out of 10, Exceptional, (168)
"Had the best week staying at the beautiful Tipsy Turtle! Property & home were both well maintained, immaculately cleaned & well stocked with a ton of essentials. Perfect vacation for relaxing when u want or being active with unlimited kayaking or paddle boarding. Scott was a pleasure to deal with & everything was great, we look forward to staying here in the future. "
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
Charming oceanfront condo with pool, beach access, tennis, & washer/dryer
Marina
Charming oceanfront condo with pool, beach access, tennis, & washer/dryer
3.0 out of 10, (2)
"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
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
Outdoor pool, a heated pool
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
10.0 out of 10, Exceptional, (108)
"This is an outstanding property, and we will definitely be staying there again in the future!"
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
Pool
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
9.6 out of 10, Exceptional, (16)
"Location , staff , general area, cleanliness all were excellent. Loved our condo."
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
Peacock Shores Islamorada - Vacation On The Beach!
Beach nearby, sun loungers, beach towels
Peacock Shores Islamorada - Vacation On The Beach!
10.0 out of 10, Exceptional, (31)
"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!
Relaxing waterfront retreat with boat dock & amazing ocean views
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
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
Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
5.0 star property
9.0 out of 10, Wonderful, (1003)
"We were forced to leave a day early due to mold in the room and have contacted Expedia for a refund which they are working on."
The price is CA $418
CA $564 total
includes taxes & fees
Nov 22 - Nov 23
Cheeca Lodge & Spa
Amara Cay Resort
Exterior
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1211)
"My family truly enjoyed this resort. Extremely satisfied. We are your customers from now on. Thank you. "
The price is CA $217
CA $337 total
includes taxes & fees
Dec 3 - Dec 4
Amara Cay Resort
Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1366)
"The Staff was very accommodating. The room was clean and equipped with a microwave, refrigerator, and very comfortable Robes. We loved the view and the peacefulness."
The price is CA $198
CA $292 total
includes taxes & fees
Dec 8 - Dec 9
Chesapeake Beach 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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find a vacation rental in Islamorada?

Yes, we have vacation rentals close to well known points of interest in Islamorada, or you can choose a more remote 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 vacation home rentals that Islamorada has to offer?

TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, and more: Visitors like this Islamorada vacation home rental. It is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. Our travelers also rate Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool as a favorite home for rent in Islamorada.

How many vacation rentals are there in Islamorada?

With 595 Expedia vacation rentals, you're sure 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 Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

What’s a vacation rental in Islamorada like?

A vacation rental is a private property where you can stay for a couple of days or more in Islamorada. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.