Islamorada Holiday Rentals

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Check prices for these dates

Tonight
21 Apr - 22 Apr
Tomorrow
22 Apr - 23 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

Holiday Rentals in Islamorada

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (452)
"The resortbis very nice for a budget keys place. The ubit was great. Very clean. The property offers a lot and its so close to bud and marys. The only issue we found was how loud it is inside the unit. Paper thin walls. If youre ok with that, cant beat the place."
The price is HK$942
HK$1,184 total
includes taxes & fees
27 Apr - 28 Apr
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (57)
"Such a beautiful, quiet and clean location. The staff were attentive and helpful. "
The price is HK$4,132
HK$5,077 total
includes taxes & fees
11 May - 12 May
The Islands of Islamorada
Beach Residence / Private overwater dock / Heated Pool / Mahi Key
Miscellaneous

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
A heated pool

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

10.0 out of 10, Exceptional, (177)
"Wonderful, well-maintained, clean home in paradise! Roger and Linda communicated before, during and after our stay to make sure everything was perfect. Morning coffee on the porch, lunch by the pool, and several delicious restaurants for dinner, nearby. Our teens had plenty to do from swimming, to fishing in the boat basin, and fishing charters out of Key Largo. A day trip to Key West is also very manageable. We loved the daily manatee visits to the boat docks on the property. A safe, quiet...
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
Smart TV

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!
Outdoor dining

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

9.6 out of 10, Exceptional, (77)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
Private Beachfront Paradise
Outdoor pool

Private Beachfront Paradise

9.8 out of 10, Exceptional, (67)
"Had a great time, the house is exactly like the pictures"
Private Beachfront Paradise
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Terrace/patio

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

10.0 out of 10, Exceptional, (81)
"If you are lucky enough to find an opening for this house, just book it.The house and property are truly exceptional. Everything is thoughtfully labeled in the house, which is really handy when you just want to know what light switch turns on which light! The kitchen and bathrooms are VERY well stocked.The canal out back is very nice and my kids actually caught some cool fish out there. Manatees came to visit there are well. We loved the kayaks and paddle boards. The home is over 100 years old...
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
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)
"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
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, (98)
"We loved everything about this house! The outdoor areas were perfect. We had everything we needed to have a great time at the house but close enough to venture out and explore the keys if we wanted. Owners were responsive and great to work with"
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
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, (111)
"Love Chausie and her properties! Top notch! "
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
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, (24)
"We had a great stay in Islamorada. The Bungalow met all of our needs. All of the very basic necessities were provided. No frills but clean with warm shared pool and easy access to everything nearby. Owners were very responsive for the couple of questions we had during our stay. "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
BeachFront Paradise/By The Glam Homes
Beach

BeachFront Paradise/By The Glam Homes

BeachFront Paradise/By The Glam Homes
Gorgeous Ocean Views, Ground Floor Studio
Pool

Gorgeous Ocean Views, Ground Floor Studio

10.0 out of 10, Exceptional, (7)
"Worth the visit. We will be back. "
Gorgeous Ocean Views, Ground Floor Studio
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (88)
"With a tiki bar, hammock, pool access, and hot tub, we spent most of our time enjoying the sunny weather. The place was super clean, very comfortable and a perfect March get-away for us. Captain Rob was attentive and offered top-notch local recommendations. Highly recommend! We had our two young-adult sons with us and we were comfortable, but we were at capacity. "
The price is HK$4,338
HK$7,406 total
includes taxes & fees
30 Apr - 1 May
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
Terrace/patio

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
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, (53)
"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 #3 - 2 Bed/1 Bath & Pool in Islamorada
Outdoor pool, a heated pool

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

9.0 out of 10, Wonderful, (12)
"Great property. Not the property’s fault but I was eaten up by bugs. Definitely bring bug spray. "
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
Outdoor pool, a heated pool

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
A heated pool

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

10.0 out of 10, Exceptional, (34)
"We enjoyed our stay at this condo location. The property was well maintained, clean and the owner very receptive and prompt with answers to questions. Location was perfect. We could walk to several restaurants if we desired. I would stay here again in a heartbeat"
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
Private beach, white sand, sun-loungers, beach towels

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1434)
"Property location was good. The views were beautiful. Lots of lounge chairs and space for everyone. We went during the week and felt like we were in an exclusive place. Front desk staff were beyond excellent. Restaurant next door was fabulous. Fresh fish and great drinks. The bed in the Villa was super comfy. Plenty of towels and amenities. I give it a great recommendation . "
The price is HK$1,622
HK$2,261 total
includes taxes & fees
28 Apr - 29 Apr
Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3 outdoor pools, a heated pool, pool umbrellas, pool loungers

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

3.5 star property
9.2 out of 10, Wonderful, (19)
"We loved the hotel. Perfect weekend getaway with our dog. It really is pet friendly and everyone is super nice. Loved all the dinning options as well as the amount of different spaces to be at. Definitely will be coming back! "
The price is HK$2,104
HK$2,883 total
includes taxes & fees
12 May - 13 May
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Cheeca Lodge & Spa
Private beach, sun-loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1066)
"Beautiful property all around! Plenty of activities on property. Great food at the on property Atlantic's Edge Restaurant. Beautiful 'beach' but it's not especially sandy at all. Poor daily room refresh, may or may not complete the process. Leaky above counter sink, bugs in room (both dead and alive), glasses left on walkway outside our 3 floor room (a few got broken and broken glass left all over), vacuum cleaner left in elevator daily. Pizza box left for days on outside trash can by the...
The price is HK$1,505
HK$2,216 total
includes taxes & fees
12 May - 13 May
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 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?

Beach Residence / Private overwater dock / Heated Pool / Mahi Key: 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. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 holiday rentals are there in Islamorada?

With 590 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 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 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.