Islamorada Holiday Rentals

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17 Nov - 18 Nov
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18 Nov - 19 Nov
This weekend
21 Nov - 23 Nov
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28 Nov - 30 Nov

Holiday Rentals in Islamorada

25-inch flat-screen TV with digital channels, TV
Treasure Harbor

Treasure Harbor

3.0 star property
Islamorada
9.0 out of 10, Wonderful, (111)
"The houseboat was so cute! The staff was very friendly and helpful. We really enjoyed out stay. The pool was new and clean. We would definitely come back."
United States
Tracie
Treasure Harbor
Exterior
Breezy Palms Resort

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (567)
"Best hotel for the price"
United States
luzdari
The price is HK$538
HK$1,008 total
includes taxes & fees
18 Nov - 19 Nov
Breezy Palms Resort
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers
The Islands of Islamorada

The Islands of Islamorada

4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (68)
"Beautiful property!"
United States
Betty
The price is HK$4,538
HK$5,534 total
includes taxes & fees
18 Nov - 19 Nov
The Islands of Islamorada
Outdoor pool, a heated pool
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

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

Matecumbe
9.6 out of 10, Exceptional, (32)
"Nice and convenient location. "
United States
Daniel D.
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Terrace/patio
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Matecumbe
10.0 out of 10, Exceptional, (86)
"House was perfect for our family vacation."
United States
Jackie G.
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
On the beach, sun-loungers, beach towels
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen

Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen

Islamorada
9.8 out of 10, Exceptional, (34)
"Very private. Exactly like photos."
United States
jane b.
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen
Outdoor pool, a heated pool
Islamorada Boaters Paradise with 70' Dock and private beach access..

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

Matecumbe
10.0 out of 10, Exceptional, (24)
"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. "
United States
Susan H.
Islamorada Boaters Paradise with 70' Dock and private beach access..
Terrace/patio
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

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

Islamorada
10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
United States
Isabella
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
Property grounds
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

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

Venetian Shores
10.0 out of 10, Exceptional, (38)
"We enjoyed our stay so much. This house was a dream. It had all we need to make out keys getaway unforgettable! "
United States
Milena P.
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
Exterior
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

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

Islamorada
10.0 out of 10, Exceptional, (200)
"This was a perfect place for two couples. The house was lovely, the pool was perfect and everyone was so friendly. Craig's place was clean and comfortable. He was easy to communicate with and did everything to make our stay five stars! Would definitely recommend this home "
United States
Anonymous traveller
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Sun-loungers
BeachFront Paradise/By The Glam Homes

BeachFront Paradise/By The Glam Homes

Matecumbe
10.0 out of 10, Exceptional, (1)
"Professional communication with the host. Great pool. Enough beds to sleep everyone comfortably. Loved having the second fridge too."
United States
Alex F.
BeachFront Paradise/By The Glam Homes
Outdoor dining
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

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

Matecumbe
9.6 out of 10, Exceptional, (86)
"Our stay was great, close to everything! Loved the Manitees that came right into the harbor! The house was very clean and just the right size for 4."
United States
Lorraine C.
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
A heated pool
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

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

Islamorada
9.8 out of 10, Exceptional, (153)
"Great place! Exactly as described."
United States
Angela K.
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
A heated pool
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

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

Islamorada
10.0 out of 10, Exceptional, (185)
"Overall a good trip. A few items needed to be taken care of, but it didn't stop us from having a great time."
United States
Darrell P.
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Exterior
Final open week of 2026 - Dec 13th - 20th Stunning Oceanfront Estate

Final open week of 2026 - Dec 13th - 20th Stunning Oceanfront Estate

Matecumbe
10.0 out of 10, Exceptional, (57)
"Amazing property! "
United States
Stefanie P.
Final open week of 2026 - Dec 13th - 20th Stunning Oceanfront Estate
Outdoor pool, a heated pool
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!

Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!

Venetian Shores
9.6 out of 10, Exceptional, (58)
"Second stay in 3 years. Highly recommend!"
United States
Don B.
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!
On the beach, sun-loungers, beach towels
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

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

Matecumbe
10.0 out of 10, Exceptional, (106)
"The property was a perfect fit for our three family spring break. Plenty of ways to relax and enjoy the property and great location to all that Islamorada and the surrounding area has to offer. Super friendly and attentive hosts, a well appointed property and a view that we’ll never forget. "
United States
Chip W.
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
Outdoor pool, a heated pool
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Matecumbe
10.0 out of 10, Exceptional, (120)
"Wonderful location."
United States
Keith M.
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
Exterior
Anglers Reef Islamorada Oceanfront 3BR Pool Front Home Private Beach & Boat Dock

Anglers Reef Islamorada Oceanfront 3BR Pool Front Home Private Beach & Boat Dock

Islamorada
Anglers Reef Islamorada Oceanfront 3BR Pool Front Home Private Beach & Boat Dock
Outdoor pool, a heated pool
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

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

Matecumbe
9.2 out of 10, Wonderful, (16)
"Overall the property was nice. Very quaint. A previous review mentioned how small the bathroom was. I agree, but for us it wasn't a huge ordeal. I would say it made it challenging when trying to get ready because the sink takes up all the counter space. Luckily there is a wall shelf in the kitchen that we utilized. Would be nice to have mirrors in the bedrooms, and maybe some shelving in the bathroom to set items on during the stay. Our front door seemed to lack the shades that the other...
United States
Tracie C.
Bungalow #3 - 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

Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"Great beach. Clean room. Helpful staff. Kitchen was big help to stay healthy and keep costs down. Best part was large screened in porch. Great value. Lots of restaurants in walking distance. "
Vicki 3-night trip
Posted 21 hours ago
Breezy Palms Resort

Find out more about Islamorada

Search for holiday rentals in Islamorada on Expedia! You can easily find your home rentals, villas, holiday apartments in Islamorada using one of the methods below:

  • View our selection of featured holiday rentals in Islamorada
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Look no further and take a look at our great range of rental properties in Islamorada!

Frequently asked questions

Can I find a holiday rental in Islamorada?

Yes, there are holiday rentals close to the most popular sights in Islamorada, or you can select a more secluded 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 holiday rentals that Islamorada has to offer?

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars: This highly rated holiday home rental in Islamorada is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Islamorada include Islamorada Boaters Paradise with 70' Dock and private beach access.. and Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip. .

How many holiday rentals are there in Islamorada?

With 488 Expedia holiday rentals, you're guaranteed 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 holiday rental in Islamorada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islamorada. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.