List your Property
Sunset Drive Beach, Islamorada, Florida, United States of America

Sunset Drive Beach vacation rentals

We found 382 vacation rentals — enter your dates for availability

Discover a selection of 382 vacation rentals in Sunset Drive Beach that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $200 per night, and houses and condos are popular options for a stay in Sunset Drive Beach. Either way, you'll find a rental for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find spaces that suit your style

Houses

View 252 Houses

Condos/Apartments

View 68 Condos/Apartments

Resorts

View 18 Resorts

Townhouses

View 16 Townhouses

Hotels

View 32 Hotels

Find the best place to stay — Sunset Drive Beach

Relaxing waterfront retreat with boat dock & amazing ocean views

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$341 avg/night
(3)

Beautiful Islamorada Beach Home directly ON the beach

4 Bedrooms · 3 Bathrooms
$499 avg/night
(1)

Charming Beach Front Home in Lower Matecumbe - 113 Sunset Dr.

Sleeps 8 · 4 Bedrooms · 3 Bathrooms
$572 avg/night
(10)

Ocean Front, Sunrise and Sunset View, Private Beach, Dockage

Sleeps 4 · 1 Bedroom · 1 Bathroom
$200 avg/night

You will never want to leave

Sleeps 6 · 3 Bedrooms · 3 Bathrooms
$1,150 avg/night
(1)

Beautiful bayfront home with sandy beach, pool and dockage all located on a private half acre!

4 Bedrooms · 4 Bathrooms
$1,000 avg/night

Search 382 vacation rentals

Top rated rentals — Sunset Drive Beach
Stayed Jan 2023

Keys Vacation

Property listing is exactly as advertised. Very updated, clean, comfortable and well maintained. Conveniently located to all attractions, restaurants and stores. Very safe neighborhood with friendly people. Would definitely rent again and highly reco...

Danielle P.
Danielle P.
Stayed Dec 2022

This place is perfect!

Everything about this place is perfect: the location, the view, the accommodations and the excellent communication from the owner. The place is spacious and clean, with comfortable beds and a huge deck with an incredible view. The kitchen is very wel...

Krista W.
Krista W.

Maple Grove, MN

Stayed Dec 2022

Love this condo!!

First time in this condo and it was great and beautifully decorated. Very comfortable and had all the things we needed for our stay. Lenore was very attentive and wonderful to work with. She answered all of our questions and very helpful. Property wa...

Tammie F.
Tammie F.
Stayed Dec 2022

Amazing

This property was just perfect!!! The views were so wonderful. The pool was again wonderful!! If i could give this location 10 stars I would. Im a Florida native and have been to the Keys over a dozen times but it had been 10 years. This property was...

Melissa B.
Melissa B.
Stayed Dec 2022

Perfect cottage in the Keys

This cottage was absolutely perfect for a weekend get away. Very clean, no problem with appliances, and a short walk to the pool. There were inside lights (like an alarm, fire, or motion) within the living room that went off randomly throughout the d...

Marissa B.
Marissa B.
Stayed Nov 2022

Peaceful location with amenities nearby

We arrived here during the onset of Tropical Storm Nicole, and the skies were blustery and equally beautiful. The unit was spotless, spacious and well equipped. The back door offered a beautiful view of the Gulf of Mexico and a soft breeze. The venue...

Andrew K.
Andrew K.

Jupiter, FL

Stayed Aug 2022

The water was not as clear with lots of seaweed. The downstairs ac was not working good needed batte

excellent house, ac downstairs did not work at all when we got there, the thermostat needed batteries, we put batteries and it worked after that but did not get cooler than 75. Also, when it rained, downstairs unit was leaking from somewhere into the...

ken o.
ken o.
Stayed Aug 2022

Amazing Vacation!

This property was excellent! Everything was just like in the pictures. It was great being in driving range of all the keys being right in the middle. I wish there were some beach chairs and/or an umbrella available to use but really it was a beautifu...

Ryan W.
Ryan W.
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

How many vacation rentals are available around Sunset Drive Beach?

Our 2023 property listings offer a large selection of 382 vacation rentals around Sunset Drive Beach. From 252 house rentals to 68 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.