Islamorada Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 7 - Aug 8
Tomorrow
Aug 8 - Aug 9
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Islamorada

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (502)
"Best kept secret, love staying here,!"
The price is ￥11,321
￥20,368 total
includes taxes & fees
Sep 7 - Sep 8
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, (93)
"Unique House boat experience, friendly staff. "
The price is ￥13,249
￥35,608 total
includes taxes & fees
Sep 2 - Sep 3
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, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ￥80,971
￥99,208 total
includes taxes & fees
Aug 11 - Aug 12
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, (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
A heated pool

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
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, (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
Outdoor pool, a heated pool

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
Outdoor pool

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..
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (22)
"We loved this house. It had plenty of space for all 8 of us. We enjoyed fishing off the dock, the pool and the private beach. "
Islamorada Boaters Paradise with 70' Dock and private beach access..
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, (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
Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.
Fridge, microwave, oven, stovetop

Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.

7.4 out of 10, Good, (3)
"Three generations stayed very comfortably in this great house. It was located great for food and activities!"
Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
Terrace/patio

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
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
Outdoor pool, a heated pool

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.
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, (81)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Exterior

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
A heated pool

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
Waterfront / Ocean Access Canal / Kamp Key / Homes
Dining

Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Oceanfront-Spacious 4 BR home, NEW Kitchen, Pool & Beach, 31' Boat Slip INCLUDED
On the beach, sun loungers, beach towels

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
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
On the beach, sun loungers, beach towels

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

10.0 out of 10, Exceptional, (115)
"The property and the location was absolutely perfect. "
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
A heated pool

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

9.8 out of 10, Exceptional, (153)
"Great place! Exactly as described."
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great resort with lots to do on-site, pool/kayak/paddle boards/chess/checkers. Morning omelette was delicious & breakfast with the iguanas was fun! Great spot if you’re traveling through or on a fishing trip."
EDEN 2-night trip
Posted 2 days ago
Chesapeake Beach Resort

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.