Islamorada Vacation Rentals

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Check prices for these dates

Tonight
Mar 30 - Mar 31
Tomorrow
Mar 31 - Apr 1
Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13

Vacation Rentals in Islamorada

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (431)
"I loved the vintage Florida feel 0f the property."
The price is ￥20,918
￥31,300 total
includes taxes & fees
Mar 31 - Apr 1
Breezy Palms Resort
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, (54)
"Above and beyond service. "
The price is ￥86,757
￥105,861 total
includes taxes & fees
Apr 6 - Apr 7
The Islands of Islamorada
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, (175)
"Rodger and Linda is home and Islamorada is wonderful. They are unbelievably accommodating property owners and made the trip extra special. I look forward to returning and staying there again."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25
Terrace/patio

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

9.8 out of 10, Exceptional, (79)
"Three generations of our family enjoyed a wonderful vacation at The Last Resort. The house was beautifully appointed and well stocked as described in the listing. It had everything we needed for a memorable beach vacation. The owner was friendly, helpful, and easy to communicate with. We hope to return! back!ThownerfrieThowwith. "
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25
Beach Residence / Private overwater dock / Heated Pool / Mahi Key
Miscellaneous

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

The price is ￥188,641
￥330,127 total
includes taxes & fees
Apr 13 - Apr 14
Beach Residence / Private overwater dock / Heated Pool / Mahi Key
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, (87)
"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 ￥83,761
￥141,936 total
includes taxes & fees
Apr 30 - May 1
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
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 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, (96)
"We have stayed in the keys several times at various different houses. This was by far our favorite. The attention to detail in how the home and grounds were set up was truly exceptional. The pictures and videos in the listing are obviously very slickly produced, but the property lives up to all of the hype. You will not be disappointed!"
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
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
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, (109)
"This is our 2nd stay at this amazing home. Everything was perfect! This vacation rental has everything you could need for a fabulous stay in Islamorada!!! Excellent location for dining and well as a quick boat ride out to the sandbar. Our teens spent hours catching fish from the dock! Periodic visits from the local manatees was spectacular. We can’t wait to return to paradise next year!"
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
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
Private Beachfront Paradise
Outdoor pool

Private Beachfront Paradise

9.6 out of 10, Exceptional, (65)
"Good location "
Private Beachfront Paradise
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, (19)
"Beautiful little two bedroom cottage completely renovated.close to mice restaurants/bars."
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
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
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
Outdoor pool, a heated pool

Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip

10.0 out of 10, Exceptional, (111)
"Beautiful property and facilities. Great location "
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
AQUAMARINE OCEANVIEW “”FLASH SALE 4/5-4/12/2025”””FREE DOCK+POOL+GYM+150 REVIEWS
Aerial view

AQUAMARINE OCEANVIEW “”FLASH SALE 4/5-4/12/2025”””FREE DOCK+POOL+GYM+150 REVIEWS

10.0 out of 10, Exceptional, (150)
"Everything was spot on! The property was as advertised, and our host was awesome. We have stayed in many vrbo properties, and hands down this was our best host ever. She genuinely wanted us to have a great visit. Thank you!"
AQUAMARINE OCEANVIEW “”FLASH SALE 4/5-4/12/2025”””FREE DOCK+POOL+GYM+150 REVIEWS
RELAX in your PRIVATE Oceanfront Cottage!
Lake

RELAX in your PRIVATE Oceanfront Cottage!

10.0 out of 10, Exceptional, (103)
"Our third time staying here was as wonderful as the first two. So peaceful and comfortable. All the comforts of home, close to grocery, restaurants and pharmacy if needed. It’s just the best place to stay when escaping the northern states for a little warmth and sunshine in mid winter. I can’t imagine staying anywhere else in the Keys.This place is our favorite of favorites!"
RELAX in your PRIVATE Oceanfront Cottage!
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, (32)
"Beautiful property!"
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
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
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, (1606)
"Beautiful pool, beach and hot tub. My son loved the waffle guy at breakfast. "
The price is ￥38,809
￥52,088 total
includes taxes & fees
Mar 31 - Apr 1
Chesapeake Beach 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, (1218)
"Always have the most beautiful time at Cheeca."
The price is ￥40,637
￥55,831 total
includes taxes & fees
Apr 27 - Apr 28
Cheeca Lodge & Spa
Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
9.0 out of 10, Wonderful, (1491)
"Great staff"
The price is ￥50,459
￥66,712 total
includes taxes & fees
Apr 27 - Apr 28
Amara Cay Resort
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?

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25: Visitors like this Islamorada vacation home rental. It is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a rooftop terrace, a private yard, and a selection of games so you can immerse yourself in your vacation. Our travelers also rate 5 bedroom - Deep Dockage & Heated Pool in Islamorada. as a favorite home for rent in Islamorada.

How many vacation rentals are there in Islamorada?

With 602 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 Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

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.