3771+ Private Villas and Holiday Rentals in Sunset Key |
Sunset Key Holiday Rentals
New
House
4 Bedrooms
4 Baths
8 Guests
2386 ft²
Private Pool
Hot Tub
Fireplace/Heating
Pool
US $1,430/Night
7 Nights - US $10,010
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
- Pool
View
Breakfast
Parking
US $953/Night
7 Nights - US $6,673
House
8.6Fabulous
(1006 Reviews)
1 Bedroom
1 Bath
- Pool
Ocean View
Balcony/Terrace- View
US $280/Night
7 Nights - US $1,961
New
House
3 Bedrooms
3 Baths
6 Guests
1615 ft²
- Private Pool
Oceanfront- Pool
- Ocean View
US $889/Night
7 Nights - US $6,225
House
- Key West
- ·
- Uptown - Upper Duval
- 0.06 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
Pet Friendly
Child Friendly
Security/Safety
US $364/Night
7 Nights - US $2,548
New
House
- Key West
- ·
- Key West Historic District
- 0.10 mi to center
4 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $688/Night
7 Nights - US $4,819
New
House
4 Bedrooms
2 Baths
10 Guests
1800 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $423/Night
7 Nights - US $2,964
House
2 Bedrooms
2 Baths
4 Guests
1099 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $320/Night
7 Nights - US $2,242
New
House
3 Bedrooms
3 Baths
5 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $239/Night
7 Nights - US $1,675
Luxury Holiday Rentals in Sunset Key
Over 3762+ Luxury Holiday Rentals in or Near Sunset Key
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
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Top-Rated Holiday Rentals with a Pool in Sunset Key
Over 2764+ The Best Private Villas and Holiday Rentals in Sunset Key with a Pool
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(218 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $403/Night
7 Nights - US $2,824
House
- Key West
- ·
- Uptown - Upper Duval
- 0.02 mi to center
10.0Exceptional
(202 Reviews)
3 Bedrooms
3 Baths
6 Guests
1154 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,059/Night
7 Nights - US $7,411
House
10.0Exceptional
(194 Reviews)
3 Bedrooms
3 Baths
7 Guests
1855 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
US $1,384/Night
7 Nights - US $9,689
House
- Key West
- ·
- Truman Annex
- 0.17 mi to center
10.0Exceptional
(192 Reviews)
2 Bedrooms
2 Baths
4 Guests
1080 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $659/Night
7 Nights - US $4,611
Condo
- Key West
- ·
- Truman Annex
- 0.20 mi to center
10.0Exceptional
(192 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $326/Night
7 Nights - US $2,281
House
10.0Exceptional
(186 Reviews)
2 Bedrooms
2 Baths
6 Guests
765 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $661/Night
7 Nights - US $4,629
Condo
- Key West
- ·
- Bahama Village
- 0.14 mi to center
10.0Exceptional
(176 Reviews)
2 Bedrooms
1 Bath
4 Guests
680 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $395/Night
7 Nights - US $2,768
Condo
10.0Exceptional
(170 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
US $555/Night
7 Nights - US $3,882
Condo
10.0Exceptional
(167 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $311/Night
7 Nights - US $2,180
Pet-Friendly Holiday Rentals in Sunset Key
Over 1106+ Pet-Friendly Holiday Rentals in or Near Sunset Key
Apartment
10.0Exceptional
(96 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Pet Friendly
- Kitchen
Air Conditioner
Internet
US $391/Night
7 Nights - US $2,740
House
- Key West
- ·
- Uptown - Upper Duval
- 0.10 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
785.77 ft²
- Pet Friendly
- Child Friendly
- Security/Safety
US $830/Night
7 Nights - US $5,809
Apartment
- Key West
- ·
- Historic Seaport
- 0.10 mi to center
9.4Exceptional
(9 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $459/Night
7 Nights - US $3,211
Condo
10.0Exceptional
(74 Reviews)
1 Bedroom
1 Bath
4 Guests
731 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $417/Night
7 Nights - US $2,920
House
- Key West
- ·
- Uptown - Upper Duval
- 0.12 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
8 Guests
882.64 ft²
- View
- Breakfast
- Pet Friendly
- Child Friendly
US $535/Night
7 Nights - US $3,745
Condo
- Key West
- ·
- Uptown - Upper Duval
- 0.12 mi to center
10.0Exceptional
(66 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $538/Night
7 Nights - US $3,766
House
- Key West
- ·
- Uptown - Upper Duval
- 0.05 mi to center
10.0Exceptional
(41 Reviews)
3 Bedrooms
3 Baths
8 Guests
1370 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $825/Night
7 Nights - US $5,776
House
- Key West
- ·
- Uptown - Upper Duval
- 0.09 mi to center
10.0Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $1,565/Night
7 Nights - US $10,952
Condo
10.0Exceptional
(34 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $671/Night
7 Nights - US $4,700
Large Holiday Rentals and Private Villas in Sunset Key
Over 373+ Large Holiday Rentals and Private Villas in or Near Sunset Key
Villa
10.0Exceptional
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $325/Night
7 Nights - US $2,276
House
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
4 Baths
12 Guests
2346.53 ft²
- Internet
- Child Friendly
Laundry- Security/Safety
US $2,693/Night
7 Nights - US $18,854
Villa
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $506/Night
7 Nights - US $3,541
House
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
12 Guests
2443.41 ft²
- Fireplace/Heating
- Pool
- View
- Parking
US $2,823/Night
7 Nights - US $19,762
Villa
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $506/Night
7 Nights - US $3,541
Villa
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $288/Night
7 Nights - US $2,013
Villa
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
350 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $314/Night
7 Nights - US $2,199
House
- Key West
- ·
- Uptown - Upper Duval
- 0.05 mi to center
2 Bedrooms
5 Baths
14 Guests
2571 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $2,096/Night
7 Nights - US $14,671
Villa
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $483/Night
7 Nights - US $3,384
Wheelchair Accessible Holiday Homes in Sunset Key
Over 672+ Wheelchair Accessible Holiday Homes in or Near Sunset Key
Condo
10.0Exceptional
(148 Reviews)
2 Bedrooms
2 Baths
6 Guests
1463 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $489/Night
7 Nights - US $3,420
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $474/Night
7 Nights - US $3,318
Resort
- Key West
- ·
- Historic Seaport
- 0.17 mi to center
9.0Exceptional
(1002 Reviews)
1 Bath
- Spa
- Pool
- Ocean View
- Balcony/Terrace
US $316/Night
7 Nights - US $2,210
Condo
10.0Exceptional
(127 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
US $561/Night
7 Nights - US $3,927
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Ocean View
- View
- Pet Friendly
- Parking
US $276/Night
7 Nights - US $1,932
Condo
10.0Exceptional
(60 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Hot Tub
- Spa
- Pool
- Ocean View
US $710/Night
7 Nights - US $4,967
Condo
10.0Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $508/Night
7 Nights - US $3,556
Condo
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
6 Guests
1325 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $677/Night
7 Nights - US $4,739
Condo
- Key West
- ·
- Truman Annex
- 0.11 mi to center
10.0Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $679/Night
7 Nights - US $4,756
Sunset Key Private Villas and Holiday Homes Under $200
Over 284+ Sunset Key Private Villas and Holiday Homes Under $200
New
House
- Key West
- ·
- Truman Annex
- 0.19 mi to center
1 Bedroom
1 Bath
2 Guests
5522 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $174/Night
7 Nights - US $1,221
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
710.42 ft²
- Pool
- View
- Pet Friendly
- Parking
US $190/Night
7 Nights - US $1,330
Hotel
7.8Very Good
(1144 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $196/Night
7 Nights - US $1,369
House
- Key West
- ·
- Bahama Village
- 0.11 mi to center
10.0Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $190/Night
7 Nights - US $1,331
Bed & Breakfast
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
9.0Exceptional
(1414 Reviews)
11 Bedrooms
7 Baths
18 Guests
235.27 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $199/Night
7 Nights - US $1,393
Apartment
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
475 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $139/Night
7 Nights - US $970
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
680 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $190/Night
7 Nights - US $1,328
Condo
- Key West
- ·
- Truman Annex
- 0.17 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
513 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $193/Night
7 Nights - US $1,348
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $183/Night
7 Nights - US $1,284
Instantly Bookable Holiday Homes in Sunset Key
Over 2386+ Instantly Bookable Holiday Homes in or Near Sunset Key
New
Hotel
3 Baths
- Pool
- Kitchen
- Parking
- Air Conditioner
US $833/Night
7 Nights - US $5,833
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1266 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $261/Night
7 Nights - US $1,826
Cottage
- Key West
- ·
- Bahama Village
- 0.13 mi to center
10.0Exceptional
(161 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $363/Night
7 Nights - US $2,543
House
10.0Exceptional
(137 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $713/Night
7 Nights - US $4,991
House
- Key West
- ·
- Key West Historic District
- 0.12 mi to center
10.0Exceptional
(130 Reviews)
2 Bedrooms
2 Baths
4 Guests
840 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $646/Night
7 Nights - US $4,522
Condo
- Key West
- ·
- Key West Historic District
- 0.38 mi to center
10.0Exceptional
(108 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $384/Night
7 Nights - US $2,689
Apartment
- Key West
- ·
- Key West Historic District
- 0.09 mi to center
10.0Exceptional
(90 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $715/Night
7 Nights - US $5,003
Cottage
- Key West
- ·
- Historic Seaport
- 0.13 mi to center
10.0Exceptional
(80 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $558/Night
7 Nights - US $3,903
House
10.0Exceptional
(78 Reviews)
2 Bedrooms
1 Bath
4 Guests
1080 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $991/Night
7 Nights - US $6,940
Book a Last Minute Place to Stay in Sunset Key
About Casai's Private Villas and Holiday Rentals in Sunset Key
Discover more than 3771 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 788.7 ft², with nightly prices averaging US $763.
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.
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Top Accommodation Types in Sunset Key
| Type | Count |
|---|---|
| Vacation Homes | 1935 |
| Holiday Apartments | 528 |
| Cottages | 108 |
| Villas | 29 |
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.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
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:
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- 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
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Everything Key West has to offer @ Mango Cottage
- Key West Rooster
- Key West Beachfront Luxury 2/2 Condo A212
- Your Condo by the Beach with Ocean View
- Heart of Downtown Key West Cottage With Off-Street 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.
- Tropical Oasis in the Truman Annex with a private pool
- Key West Harbor Inn - Adults Only
- Great Location- Remodeled Condo- Old Town-Truman Annex Close to all attractions
- 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:
- Enjoy More Privacy in a Truman Annex End Unit Townhome
- Somewhere on the beach
- La Concha Key West, Autograph Collection
How many Casai.com holiday rentals are available in Sunset Key?
As of 2026, Casai boasts over 3771 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.
People Also Ask
Finding the best prices in Sunset Key
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