Islamorada Vacation Rentals

April 2025

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May 2025

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Vacation Rentals in Islamorada

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (453)
"Breezy palms resort was beautiful & so picturesque. We really enjoyed the sunrise & gorgeous views."
The price is CA $171
CA $264 total
includes taxes & fees
May 21 - May 22
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (58)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is CA $737
CA $905 total
includes taxes & fees
May 11 - May 12
The Islands of Islamorada

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

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

10.0 out of 10, Exceptional, (177)
"As alway Anglers Reef is a great place to stay and offers fantastic amenities and accommodation. The only problem was that temperamental lock for the front door. However Roger was extremely good at letting us in and out throughout our stay."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

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, (77)
"Great place great location and location"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

Private Beachfront Paradise

9.8 out of 10, Exceptional, (67)
"Property is private and beautiful. Every possible amenity is included - even paddle boards and kayaks. Private beach, heated pool right on the beach. Family felt like they were in their own private paradise. Excellent location near all the best restaurants in Islamorada. Not far from Sombrero Beach and Bahia Honda - two great beaches. Super comfortable. We asked for a Christmas tree as we were staying over Christmas and they decorated the entire house, upstairs and down. Could not have been...
Private Beachfront Paradise

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

10.0 out of 10, Exceptional, (81)
"Amazing stay, property was exactly as advertised and had everything we needed."
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

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

10.0 out of 10, Exceptional, (54)
"I have rented properties up and down the east coast This is by far and away the cleanest and most well apportioned place I have ever stayed Location is great and easy access Walking distance from lots of places Highly recommend for large adult groups "
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

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

10.0 out of 10, Exceptional, (98)
"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

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (111)
"Our family all thought this was the perfect spot for our famuly vacation"
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

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

9.6 out of 10, Exceptional, (24)
"Beautiful, spotlessly clean, comfortable, well appointed, great pool! A lovely little cottage that had everything we needed! Perfect stay!"
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

BeachFront Paradise/By The Glam Homes

BeachFront Paradise/By The Glam Homes

Gorgeous Ocean Views, Ground Floor Studio

10.0 out of 10, Exceptional, (7)
"Nice cozy place for a couples getaway. Awesome pool and oceanfront views. Many good restaurants with outside seating close by. "
Gorgeous Ocean Views, Ground Floor Studio

TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

10.0 out of 10, Exceptional, (88)
"Great stay! Amazing outdoor oasis, house was super clean, and very convenient. Host was very responsive, check in seamless, lots of great recommendations to try while we were in town! Lovely part of the keys and would happily stay again!"
The price is CA $774
CA $1,321 total
includes taxes & fees
Apr 30 - May 1
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

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

9.6 out of 10, Exceptional, (53)
"Clean nice area great place"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

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

9.0 out of 10, Wonderful, (12)
"Cute little cottage in the Florida keys, great space plus there is a pool."
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

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

10.0 out of 10, Exceptional, (136)
"We had a great time at Angler’s Reef and really enjoyed our stay. It’s close to great restaurants, shops and the supermarket. The house was super clean and comfortable. Will definitely be back! "
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.

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

10.0 out of 10, Exceptional, (34)
"We had a wonderful week in Anglers reef at Scott’s home. It was clean, well appointed and was in a wonderful location. The host was very responsive and made the week as nice as it could be. I highly recommend this property and we hope to be back!!"
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
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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Other types of properties in Islamorada you may be interested in

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1431)
"Beautiful view from room , breakfast included is nice due to price of room "
The price is CA $289
CA $403 total
includes taxes & fees
Apr 28 - Apr 29
Chesapeake Beach Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 star property
9.2 out of 10, Wonderful, (19)
"Beautiful place and Staff was attentive."
The price is CA $375
CA $514 total
includes taxes & fees
May 12 - May 13
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1064)
"Wonderful stay - beautiful grounds "
The price is CA $357
CA $496 total
includes taxes & fees
May 22 - May 23
Cheeca Lodge & Spa
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.

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?

Beach Residence / Private overwater dock / Heated Pool / Mahi Key: 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. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Islamorada include Private Beachfront Paradise and 5 bedroom - Deep Dockage & Heated Pool in Islamorada..

How many vacation rentals are there in Islamorada?

With 591 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 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.