List your Property
Anne's Beach, Islamorada, Florida, United States of America

Anne's Beach vacation rentals

We found 374 vacation rentals — enter your dates for availability

Discover a selection of 374 vacation rentals in Anne's 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 private pools. Prices start at $167 per night, and houses and condos are popular options for a stay in Anne's Beach. Either way, you'll find a rental for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find spaces that suit your style

Houses

View 245 Houses

Condos/Apartments

View 67 Condos/Apartments

Townhouses

View 16 Townhouses

Resorts

View 18 Resorts

Hotels

View 32 Hotels

Find the best place to stay — Anne's Beach

Water Front 3/3 Family and Boat Friendly Home, Great Views

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$236 avg/night
(19)

Sandy Pointe - Serene Sunsets from Your 2 Bedroom Villa

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$167 avg/night
(1)

Relaxing waterfront retreat with boat dock & amazing ocean views

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

Ocean front gated privacy with 3 bedrooms and protected boat slip.

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$344 avg/night
(20)

Bayfront Islamorada Townhome with Dock & Beach

3 Bedrooms · 2 Bathrooms
$304 avg/night

Search 374 vacation rentals

Top rated rentals — Anne's 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 Dec 2022

Manatee at the dock!

My husband, three adult kids and partner of one stayed for a week at this property. The house itself is good-well stocked but could use some TLC. Very clean and plenty of room to spread out. Modern appliances in the kitchen. Loved the wine fridge. W/...

ANITA A.
ANITA A.
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

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 Anne's Beach?

Our 2023 property listings offer a large selection of 374 vacation rentals around Anne's Beach. From 245 house rentals to 67 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.