Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (379)
"Beautiful "
The price is CA $174
CA $270 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Breezy Palms Resort

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 $645
CA $805 total
includes taxes & fees
Jan 22 - Jan 23, 2025
The Islands of Islamorada

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

10.0 out of 10, Exceptional, (5)
"We had a wonderful visit. We come every Thanksgiving. Anglers is wonderful place to stay."
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

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

9.6 out of 10, Exceptional, (75)
"Beautiful home. Very well maintained! Owner was excellent to work with and very clear instruction and communication. The only downfall( not the owners doing) but the home is at the end of the canal lots of debris gets stuck in the water. Especially when Debby came to town😉 The canal is not swim-able nor fishable since lots of people go out on their boats and come back to clean their catch. Neighbors were very nice! Nice quiet neighborhood. "
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

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

TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, Hammock

10.0 out of 10, Exceptional, (82)
"I'll start off by saying that I have stayed in many places via VRBO and have never had such great hosts as we had in Rob and Regina!! From answering my questions when I originally booked, to providing such helpful information leading up to our stay - they were both top notch! The bungalow is absolutely perfect - beautifully decorated and no detail spared. It was very clean and had everything that we needed and more! My only regret is that we weren't able to stay longer! But we will be back!...
TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, Hammock

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

House in Islamorada, in exclusive Venetian Shores.

House in Islamorada, in exclusive Venetian Shores.

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

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

9.8 out of 10, Exceptional, (62)
"The house is great for a family. The kitchen has everything you need. There are some things that could use an upgrade or fix, such as the shower heads, a couple doorknobs, dusty cabinets, and other finishes. However, none of that detracted from what this property has to offer. The incredible heated pool gave our family the best memories. The air hockey, foosball table and pac man game was a fun surprise. Loved the fire tables and really appreciated the extra propane tanks left in the shed. The...
Private Beachfront Paradise

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

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!

Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

9.8 out of 10, Exceptional, (9)
"Overall great spot just south of Robbie’s and all the main areas of Islamorada. Nice accommodations that have been recently upgraded. Pool was only a short walk away. I missed on the property listing that it only had one bathroom. For our family with two teenagers we needed two bathrooms. That’s the only complaint though. Everything else was great."
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

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

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

AQUAMARINE OCEANVIEW<-WALL to WALL->+144/BEST 5 STAR REVIEWS+DOCK+POOL+GYM++++++

10.0 out of 10, Exceptional, (144)
"Had a great time and totally enjoyed our stay! Looking forward to visiting again!! Lenore was very accessible if needed for anything. The condo is very large and accommodating and very close to all the activities we wanted to do. It has everything you could need."
AQUAMARINE OCEANVIEW<-WALL to WALL->+144/BEST 5 STAR REVIEWS+DOCK+POOL+GYM++++++

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

10.0 out of 10, Exceptional, (109)
"Location on the Key was perfect. Location within the complex was perfect. 7 adults were very comfortable, able to spread out, and all enjoyed the property."
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath with Den & Nursery

9.8 out of 10, Exceptional, (78)
"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 with Den & Nursery

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

9.8 out of 10, Exceptional, (50)
"Clean nice area great place"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
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

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1209)
"Very small oceanfront, not access, hotel with a nice outside beach bar and pool with various beach seating spots. Small but cute for staying here for 1 night."
The price is CA $564
CA $730 total
includes taxes & fees
Dec 26 - Dec 27
Amara Cay Resort

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1386)
"Loved it."
The price is CA $342
CA $457 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Chesapeake Beach Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1005)
"Excellent vacation resort"
The price is CA $423
CA $573 total
includes taxes & fees
Jan 20 - Jan 21, 2025
Cheeca Lodge & Spa
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?

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip : This Islamorada vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Our travelers also rate Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada as a favorite home for rent in Islamorada.

How many vacation rentals are there in Islamorada?

With 598 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.