Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (499)
"Excellent room and staffs!!!!!"
$138 nightly
The price is $153
Sep 2 - Sep 3
Total includes taxes and fees
Breezy Palms Resort

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (93)
"Unique House boat experience, friendly staff. "
$215 nightly
The price is $242
Sep 2 - Sep 3
Total includes taxes and fees
Treasure Harbor

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (65)
"Absolutely outstanding resort. Legitimate 5 star property. "
$503 nightly
The price is $566
Aug 4 - Aug 5
Total includes taxes and fees
The Islands of Islamorada

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

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

10.0 out of 10, Exceptional, (183)
"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

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

9.6 out of 10, Exceptional, (57)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

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

9.6 out of 10, Exceptional, (29)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

FALL SPECIALS! Islamorada Anglers Reef Oceanview: Private Beach, Pool, Marina

10.0 out of 10, Exceptional, (3)
"Our stay was nothing but amazing! The area/community is beautiful and Al was a wonderful host! Will definitely be staying here again next year!!"
FALL SPECIALS! Islamorada Anglers Reef Oceanview: Private Beach, Pool, Marina

Islamorada Boaters Paradise with 70' Dock and private beach access..

10.0 out of 10, Exceptional, (22)
"House was perfect for our Keys vacation! We were able to bring our 23ft Key West and keep it docked at the house. The house had a pool, hot tub, ice machine, fish cleaning table. Plus right down the canal is an amazing sandbar. Highly recommended this place if you have a boat. House was not far from great restaurants like Hungry Tarpon, Lazy Days & Papa Joes"
Islamorada Boaters Paradise with 70' Dock and private beach access..

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

10.0 out of 10, Exceptional, (55)
"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

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

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

9.6 out of 10, Exceptional, (81)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (116)
"Love Chausie and her properties! Top notch! "
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

10.0 out of 10, Exceptional, (193)
"Great location. Beautiful, comfortable accommodations. Would absolutely return. "
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

9.8 out of 10, Exceptional, (93)
"This is the best location we have stayed at in Islamorada. The community was safe and quiet, plenty to do right on site with swimming, private beach, kayaks and paddleboards, fishing off dock. We saw manatees most days in the marina. The house is exactly as listed, the owners were quick to respond and fix any issues we had. Would definitely rent again! "
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

Oceanfront-Spacious 4 BR home, NEW Kitchen, Pool & Beach, 31' Boat Slip INCLUDED

10.0 out of 10, Exceptional, (32)
"Everything was wonderful. House was great with beautiful water views!!!"
Oceanfront-Spacious 4 BR home, NEW Kitchen, Pool & Beach, 31' Boat Slip INCLUDED

Peacock Shores Islamorada - Vacation On The Beach!

10.0 out of 10, Exceptional, (38)
"Great place! Second time staying here. Comfortable, very clean, quiet and close to many great restaurants."
Peacock Shores Islamorada - Vacation On The Beach!

Topsider Resort

3.5 star property
8.8 out of 10, Excellent, (61)
"Its a great choice for small families looking to relax. Heated pool and hot tub. on property beach access (gulf side). Kayaks and bikes to use. inside the dwelling, master bedroom w/ full bath, another bedroom w/ two twin beds, another full bath, full kitchen + kitchenette, and living room. Really pleased. "
Topsider Resort

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

9.6 out of 10, Exceptional, (18)
"Small but great place to stay, we enjoyed the pool and it was quiet and perfect for our family."
Bungalow #5 - 2 Bed/1 Bath & Pool 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.
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Top Islamorada Hotel Reviews

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?

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards: This Islamorada vacation home rental is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games. Some other homes for rent in Islamorada include Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25 and OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars.

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 Islamorada County 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.