Sunset Key Holiday Rentals
- Key West
- Uptown - Upper Duval
- 0.09 mi to center
- Private Pool
- Oceanfront
- Pool
- Key West
- Historic Seaport
- 0.28 mi to center
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Key West
- Uptown - Upper Duval
- 0.15 mi to center
- Ocean View
- Balcony/Terrace
- View
- Key West
- Uptown - Upper Duval
- 0.03 mi to center
- Private Pool
- Oceanfront
- Pool
- View
- Breakfast
- Parking
- Private Pool
- Oceanfront
- Pool
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
- Key West
- Historic Seaport
- 0.15 mi to center
- Private Pool
- Pool
- Balcony/Terrace
Luxury Holiday Rentals in Sunset Key
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
Top-Rated Holiday Rentals with a Pool in Sunset Key
- Hot Tub
- Pool
- Balcony/Terrace
- Private Pool
- Oceanfront
- Fireplace/Heating
- Key West
- Truman Annex
- 0.20 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Key West
- Uptown - Upper Duval
- 0.16 mi to center
- Private Pool
- Pool
- Balcony/Terrace
- Key West
- Key West Historic District
- 0.13 mi to center
- Private Pool
- Oceanfront
- Pool
- Key West
- Truman Annex
- 0.21 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Key West
- Truman Annex
- 0.16 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Private Pool
- Oceanfront
- Fireplace/Heating
- Key West
- Uptown - Upper Duval
- 0.02 mi to center
- Private Pool
- Oceanfront
- Pool
Pet-Friendly Holiday Rentals in Sunset Key
- Private Pool
- Oceanfront
- Pool
- Pet Friendly
- Parking
- Internet
- Pool
- Balcony/Terrace
- Pet Friendly
- Oceanfront
- Ocean View
- Balcony/Terrace
- Key West
- Uptown - Upper Duval
- 0.10 mi to center
- Pet Friendly
- Internet
- Child Friendly
- Private Pool
- Pool
- Pet Friendly
- Pet Friendly
- Kitchen
- Air Conditioner
- Pool
- Balcony/Terrace
- Pet Friendly
- Key West
- Uptown - Upper Duval
- 0.12 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
Large Holiday Rentals and Private Villas in Sunset Key
- Hot Tub
- Pool
- Balcony/Terrace
- Key West
- Key West Historic District
- 0.15 mi to center
- Balcony/Terrace
- Child Friendly
- Barbecue/Outdoor Cooking
- Hot Tub
- Pool
- Balcony/Terrace
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Hot Tub
- Pool
- Balcony/Terrace
- Hot Tub
- Pool
- Balcony/Terrace
- Hot Tub
- Pool
- Balcony/Terrace
- Hot Tub
- Pool
- Balcony/Terrace
- Hot Tub
- Pool
- Balcony/Terrace
Wheelchair Accessible Holiday Homes in Sunset Key
- Oceanfront
- Hot Tub
- Spa
- Ocean View
- View
- Pet Friendly
- Key West
- Bahama Village
- 0.09 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Oceanfront
- Hot Tub
- Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Oceanfront
- Hot Tub
- Spa
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Oceanfront
- Hot Tub
- Spa
- Hot Tub
- Spa
- Pool
Sunset Key Private Villas and Holiday Homes Under $200
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Pool
- View
- Pet Friendly
- Child Friendly
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
- Air Conditioner
- Key West
- Truman Annex
- 0.21 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Key West
- Bahama Village
- 0.11 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Pool
- Ocean View
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Instantly Bookable Holiday Homes in Sunset Key
- Key West
- Key West Historic District
- 0.38 mi to center
- Pool
- Kitchen
- Air Conditioner
- Oceanfront
- Fireplace/Heating
- Ocean View
- Key West
- Truman Annex
- 0.20 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Key West
- Truman Annex
- 0.17 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Key West
- Bahama Village
- 0.11 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Key West
- Historic Seaport
- 0.22 mi to center
- Oceanfront
- Hot Tub
- Ocean View
- Key West
- Bahama Village
- 0.13 mi to center
- Balcony/Terrace
- Kitchen
- Parking
- Private Pool
- Oceanfront
- Fireplace/Heating
- Key West
- Key West Historic District
- 0.12 mi to center
- Oceanfront
- Hot Tub
- Ocean View
Book a Last Minute Place to Stay in Sunset Key
About Casai's Private Villas and Holiday Rentals in Sunset Key
Discover more than 3756 vacation rentals available in Sunset Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Sunset Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Sunset Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Sunset Key. On average, places to stay near Sunset Key offer 786.1 ft², with nightly prices averaging R14,148.
With Casai, finding and comparing holiday rentals in Sunset Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Sunset Key
| Type | Count |
|---|---|
| Vacation Homes | 1930 |
| Holiday Apartments | 508 |
| Cottages | 111 |
| Villas | 31 |
Use these Quick Filters to Find a Holiday Rental in Sunset Key
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Sunset Key.
Weather in Sunset Key, FL
View the weather forecast for Sunset Key before booking your Sunset Key Vacation Rentals to confirm your best time to go.
Frequently Asked Questions About Sunset Key?
What are the top holiday rentals in Sunset Key?
With numerous options available in Sunset Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Sunset Key:
- Almond Tree Inn Hotel - Adults Only
- PINEAPPLE COTTAGE, 2BR/2BA-Pvt Pool, 1/2 block to Duval
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
- Perfect Location, nPrivate Heated Pool,nPristine Luxury Home!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
How many holiday rentals have private pools in Sunset Key?
Discover a selection of holiday rentals with private pools near Sunset Key with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Everything Key West has to offer @ Mango Cottage
- Key West Harbor Inn - Adults Only
- BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
- Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Which holiday homes in Sunset Key are best for families?
If you're searching for a family-friendly holiday home in Sunset Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Sunset Key:
- Everything Key West has to offer @ Mango Cottage
- Somewhere on the beach
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
How many Casai.co.za holiday rentals are available in Sunset Key?
As of 2026, Casai boasts over 3756 properties listed in the Sunset Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Sunset Key.









































































