Islamorada Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 11 - Nov 12
Tomorrow
Nov 12 - Nov 13
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation 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, (109)
"Unique House boat experience, friendly staff. "
United States
Luis
Treasure Harbor
Exterior
Breezy Palms Resort

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (562)
"This is one of my top 5 spot to stay in the keys, clean, friendly and budget friendly, mimi is awesome "
United States
franklin
The price is ￥10,618
￥17,453 total
includes taxes & fees
Nov 16 - Nov 17
Breezy Palms Resort
2 outdoor pools, open 8:00 AM to 6:00 PM, sun 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 ￥107,394
￥129,276 total
includes taxes & fees
Nov 13 - Nov 14
The Islands of Islamorada
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, (199)
"Craig was an amazing host. The home was perfect and it is in a fabulous and safe location. We will definitely stay there again!"
United States
Gina W.
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Terrace/patio
Only 3 weeks left in 2025 for a pre-Christmas getaway! Oceanfront/Pool/dock

Only 3 weeks left in 2025 for a pre-Christmas getaway! Oceanfront/Pool/dock

Matecumbe
10.0 out of 10, Exceptional, (86)
"Everything just great except need better vaccum"
United States
Carol S.
Only 3 weeks left in 2025 for a pre-Christmas getaway! Oceanfront/Pool/dock
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..
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, (105)
"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
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 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!
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
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
Outdoor pool, a heated pool
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.

Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.

Islamorada
10.0 out of 10, Exceptional, (141)
"We were coming to the Keys before Anglers Reef was built. It is in the perfect location, close to grocery stores, restaurants, bars. Great fishing and beautiful blue waters. The pool was great, the beaches were awesome. The house was clean, beautiful and the perfect community to end our night. "
United States
JD S.
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
On the beach
Beachfront Villa w/ Pier & Pool

Beachfront Villa w/ Pier & Pool

Matecumbe
6.0 out of 10, (1)
"the room was in a great location, close to everything we wanted to do. the pier and beach was nice. The pool area was clean and nice also.Overall it was clean but the master bath was quite dated.It was not a beachfront villa as in the description. We were 8 units from the water so the description was misleading. Overall I would go again with friends or my brother and nephews as I did but not for a getaway with my wife."
United States
mike h.
Beachfront Villa w/ Pier & Pool
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
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
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, (119)
"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
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!
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!
Terrace/patio
Beautiful two- story beach house

Beautiful two- story beach house

Matecumbe
Beautiful two- story beach house
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.
View all properties
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
"Our room was beautiful and spotless. The staff was always polite, handling any inquiry or request. The location is ideal, located on the beach with easy access to the main road. They provide a nice breakfast from 6 to 10 every morning with a variety of options to choose from on top of 24-hour coffee."
Cheryl 3-night trip
Posted 1 day ago
Chesapeake Beach 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
  • Use the map to find apartments and other holiday homes in the Islamorada neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Islamorada while they last

Look no further and take a look at our great range of rental properties in Islamorada!

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?

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars: This Islamorada vacation home rental is located on the beach and has a balcony, a selection of games, and a barbecue grill 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 vacation rentals are there in Islamorada?

With 483 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 Anne's Beach, 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 Fiesta Key.

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.