Islamorada Vacation Rentals

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Check prices for these dates

Tonight
Jun 20 - Jun 21
Tomorrow
Jun 21 - Jun 22
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Islamorada

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (488)
"Laid back atmosphere with renovated rooms."
The price is ￥15,483
￥24,961 total
includes taxes & fees
Jun 24 - Jun 25
Breezy Palms Resort
Treasure Harbor
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (80)
"Very clean and great atmosphere "
The price is ￥22,054
￥45,201 total
includes taxes & fees
Jul 1 - Jul 2
Treasure Harbor
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, (61)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ￥88,450
￥107,500 total
includes taxes & fees
Jun 25 - Jun 26
The Islands of Islamorada
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25
Terrace/patio

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

10.0 out of 10, Exceptional, (82)
"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
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
Outdoor dining

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

9.6 out of 10, Exceptional, (80)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
A heated pool

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

10.0 out of 10, Exceptional, (181)
"We had a great visit! Great central location and perfect amenities for our family! Enjoyed the pool, fishing at the docks, kayaking and the comfortable space and cleanliness! Hosts checked on us every step of the way and made everything super easy! Would highly recommend for sure!! We will be back!!"
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Exterior

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
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (54)
"The house was beautiful! Immaculate, updated and large enough for our family of 14!L"
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Outdoor pool, a heated pool

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

9.6 out of 10, Exceptional, (25)
"Beautiful little two bedroom cottage completely renovated.close to mice restaurants/bars."
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Outdoor pool, a heated pool

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

9.6 out of 10, Exceptional, (55)
"This location is beautiful and the host is extremely responsive."
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
On the beach, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (102)
"This is the perfect location and home for a large gathering. 5 bedroom suites that offer privacy for each room, beautifully well stocked kitchen and everything you need for outdoors. Highly recommend!"
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
Topsider Resort
View from property

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
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
A heated pool

Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch

10.0 out of 10, Exceptional, (38)
"Beautiful property!"
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
Island Getaway: Relaxing Room w/ Balcony Steps to Sandy Beach
A heated pool

Island Getaway: Relaxing Room w/ Balcony Steps to Sandy Beach

The price is ￥48,303
￥69,345 total
includes taxes & fees
Jun 29 - Jun 30
Island Getaway: Relaxing Room w/ Balcony Steps to Sandy Beach
Private Beachfront Paradise
Outdoor pool

Private Beachfront Paradise

9.8 out of 10, Exceptional, (69)
"Good location "
Private Beachfront Paradise
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada
Outdoor pool, a heated pool

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

9.2 out of 10, Wonderful, (15)
"Cute little cottage in the Florida keys, great space plus there is a pool."
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada
Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus Cottage Oasis , With Dock
A heated pool

Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus Cottage Oasis , With Dock

10.0 out of 10, Exceptional, (10)
"Great place to stay and great host definitely will be back."
Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus Cottage Oasis , With Dock
Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10
On the beach

Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10

9.8 out of 10, Exceptional, (7)
"Amazing home for a family to enjoy. "
Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
Property grounds

Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

10.0 out of 10, Exceptional, (37)
"Was a nice property and pleasant enough for our stay."
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
Islamorada Boaters Paradise with 70' Dock and private beach access..
Outdoor pool, a heated pool

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..
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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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 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25: This Islamorada vacation home rental is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a rooftop terrace, a private yard, and a selection of games so you can immerse yourself in your vacation. Some other homes for rent in Islamorada include WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY! and OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards.

How many vacation rentals are there in Islamorada?

With 581 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 Islamorada County 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 Founders Park.

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.