Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (412)
"We only spent 3 nights, but our room was very clean and comfortable. We did have an oceanfront room, so the views were great! The room had a full kitchen and living room. I only wish there was a TV in the bedroom as well. We did not use the pool, but it looked very refreshing and well kept. The beach area was beautiful with plenty of seating, and the jetty for fishing was great for my husband. It was within walking distance to Lazy Days Restaurant and Bud & Mary's Marina. We stayed at several...
The price is CA $251
CA $356 total
includes taxes & fees
Mar 25 - Mar 26
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Lovely room with friendly staff. "
The price is CA $1,147
CA $1,368 total
includes taxes & fees
Feb 24 - Feb 25
The Islands of Islamorada

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

9.6 out of 10, Exceptional, (76)
"Great and clean place to stay. Chris was the perfect host. "
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

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

10.0 out of 10, Exceptional, (172)
"The house we stayed in was immaculate and so attractive-exactly as pictured. We felt very safe in the gated community. We used the kayaks and pool and walked the area frequently. We rented bikes and had great areas to ride in. This was a very quiet, relaxing vacation. Lots of waterside restaurants to enjoy. The owner, Roger, was a great communicator."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

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

9.6 out of 10, Exceptional, (16)
"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

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

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, (85)
"Rob and Regina were seriously the best hosts we’ve ever had! They helped us out with last minute recommendations, provided us with the most beautiful place to stay, and helped us plan the perfect vacation with 3 busy teenagers. Thank you so much, Regina and Rob, for being such kind individuals! There are so many things to do within a shirt drive from our oasis! "
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

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

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

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

10.0 out of 10, Exceptional, (50)
"I have rented properties up and down the east coast This is by far and away the cleanest and most well apportioned place I have ever stayed Location is great and easy access Walking distance from lots of places Highly recommend for large adult groups "
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

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

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

10.0 out of 10, Exceptional, (109)
"This property is perfect for a family vacation. The unit is spacious with a great view of the pool and water. Walkable to restaurants and boat rental. If you ever thought about skydiving, definitely go to I skydive Miami. Very professional with amazing views. "
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

9.8 out of 10, Exceptional, (146)
"We just spent 2 wonderful weeks at this property. Alex is an attentive host & responded immediately to a few concerns. We stayed at this property last year & have already booked for next year. The house is clean & well maintained with all the comforts of home."
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

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

10.0 out of 10, Exceptional, (110)
"Good location. Close to the pool. Lovely kitchen. Nice master bedroom. Interesting artwork on the walls. Quiet neighborhood. Negatives: Had trouble with the AC and Temp. the first 4 days. No comfortable chairs downstairs or upstairs. Just a huge couch in front of the TV area. Furniture seemed to be designed for big people. "
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip

AQUAMARINE OCEANVIEW “””FLASH SALE 3/1-3/8/25”””FREE DOCK+POOL+GYM+145 REVIEWS

10.0 out of 10, Exceptional, (146)
"We enjoyed our week staying at Aquamarine! The unit was very comfortable and clean and Lenore was a pleasure to work with. "
AQUAMARINE OCEANVIEW “””FLASH SALE 3/1-3/8/25”””FREE DOCK+POOL+GYM+145 REVIEWS

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!

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..

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (105)
"Our weeklong stay here was perfect. We enjoyed the ocean view and a visit from a manatee. The pool area and bonfire were a great way to enjoy the day and evening. We also rented a boat for the week to do some sightseeing and fishing so this place worked perfectly for this activity. The paddle boats and kayaks were a hit too. Thanks for sharing your beautiful home."
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Executive Bay w/Heated Pool, Beach, Dogs Allowed, Tennis/Pickleball

9.2 out of 10, Wonderful, (15)
"Nice property layout. Large heated pool. Close to many restaurants and tourist attractions. Some beaches in rough shape. Clear skies and beautiful sunsets. Owner replaced bbq with new weber. Thx"
Executive Bay w/Heated Pool, Beach, Dogs Allowed, Tennis/Pickleball
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, (1407)
"This is definitely a resort property with upgraded rooms, however there seemed to be more of a focus on cheezy decor rather than guest comfort. There was no table or desk in the room and only one chair. No places to have a snack or use a laptop. Wicker decorative pieces were useless. Daily resort fee charged to include breakfast - no place to eat under cover in bright sun or wet weather. Beach and pool are beautiful. Hot tub - too hot!! Unsafe for adults and especially small children - could...
The price is CA $438
CA $573 total
includes taxes & fees
Feb 23 - Feb 24
Chesapeake Beach Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1033)
"The property had a great resort feel to it. Very clean, and the staff was great. Also, the no smoking rule was great - especially around the pool and beach area."
The price is CA $481
CA $636 total
includes taxes & fees
Feb 23 - Feb 24
Cheeca Lodge & Spa

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1210)
"Amara Cay is beautiful. Everyone was polite and helpful. The beach and pool area were clean and relaxing. All rooms have a balcony except for room 209, which was our room and we paid for a balcony. No discount when that is what was advertised. Other than that it was wonderful."
The price is CA $473
CA $627 total
includes taxes & fees
Feb 24 - Feb 25
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!: This highly rated vacation home rental in Islamorada 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.

How many vacation rentals are there in Islamorada?

With 604 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 Bud n' Mary's Dive Center and Anne's Beach.

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.