Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (430)
"Quaint, clean, friendly staff! "
The price is CA $280
CA $389 total
includes taxes & fees
Mar 31 - Apr 1
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (53)
"Above and beyond service. "
The price is CA $831
CA $1,014 total
includes taxes & fees
Apr 6 - Apr 7
The Islands of Islamorada

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

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. "
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

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

10.0 out of 10, Exceptional, (175)
"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

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

10.0 out of 10, Exceptional, (87)
"This was a wonderful place to call home while visiting the beautiful Florida Keys. It was beautifully decorated, comfortable and filled with everything you could possibly need to make your vacation great. We would definitely stay here again! Highly recommended to any travelers. Wonderful host and excellent communication throughout our stay.Thank you!!!"
The price is CA $1,075
CA $1,697 total
includes taxes & fees
Mar 31 - Apr 1
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

Private Beachfront Paradise

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

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (108)
"Beautiful bay views, manatees galore, fishing off the sea wall, enough dockage for our 22 & 18 ft boats. 3 excellent master suites with great bathroom showers. Kitchen, dining room and family room all open to each other and great for gathering. Perfect pool, waterside chairs & firepit.Highly recommend!!"
5 bedroom - Deep Dockage & Heated Pool in 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!

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

9.6 out of 10, Exceptional, (52)
"Accomodations met our needs.The downstairs "apartment" was especially nice.Tiki bar was great to entertain our friends.Would have been nice to have the ice maker working, but everything else was great."
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One

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

9.6 out of 10, Exceptional, (18)
"Beautiful little two bedroom cottage completely renovated.close to mice restaurants/bars."
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

The price is CA $948
CA $2,096 total
includes taxes & fees
Apr 13 - Apr 14
Beach Residence / Private overwater dock / Heated Pool / Mahi Key

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (53)
"Fantastic! Great unit has everything we wanted and needed. Owner was great to work with hope to do again next year"
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

Gorgeous Ocean Views, Ground Floor Studio

10.0 out of 10, Exceptional, (7)
"Worth the visit. We will be back. "
Gorgeous Ocean Views, Ground Floor Studio

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

10.0 out of 10, Exceptional, (95)
"This was our second stay at the property. The location is perfect, it is on the ocean with total privacy. However, you are only minutes from all Islamorada has to offer. The home is beautiful & impeccably maintained. It is always very clean & very well equipped with all the comforts of home. The Owner / Host is always very accessible and responds to all inquiries promptly. Our group had inquired about privileges outside the norm and Chaunsey was willing to consider this which we all...
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

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

Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool

9.8 out of 10, Exceptional, (47)
"Our family enjoyed this house. The host was extremely helpful when I needed to contact her. Overall, the house was exactly as described. Particularly, I enjoyed the availability of the extra towels and we also enjoyed the quality beach towels available.The house had the amenities we needed to enjoy our week in the Florida Keys. The notebook on the counter offered plenty of suggestions for restaurants and things to do. Thank you for the fantastic stay!"
Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool

AQUAMARINE OCEANVIEW “”FLASH SALE 4/5-4/12/2025”””FREE DOCK+POOL+GYM+150 REVIEWS

10.0 out of 10, Exceptional, (150)
"Everything was spot on! The property was as advertised, and our host was awesome. We have stayed in many vrbo properties, and hands down this was our best host ever. She genuinely wanted us to have a great visit. Thank you!"
AQUAMARINE OCEANVIEW “”FLASH SALE 4/5-4/12/2025”””FREE DOCK+POOL+GYM+150 REVIEWS

Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip

10.0 out of 10, Exceptional, (111)
"Beautiful property and facilities. Great location "
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip

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!
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

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1421)
"Very clean, very beautiful. Sea on the back side love it. "
The price is CA $353
CA $478 total
includes taxes & fees
Apr 7 - Apr 8
Chesapeake Beach Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1050)
"The best of the best. "
The price is CA $573
CA $741 total
includes taxes & fees
Apr 6 - Apr 7
Cheeca Lodge & Spa

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1217)
"Un lugar perfecto para descansar "
The price is CA $451
CA $603 total
includes taxes & fees
Mar 30 - Mar 31
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 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?

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!: Visitors like this Islamorada vacation home rental. It is located by the ocean and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25 as a favorite home for rent in Islamorada.

How many vacation rentals are there in Islamorada?

With 590 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.