Sunset Key Vacation Rentals & Ski-in/Ski-out Homes
New
House
10.0Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
1564 ft²
Oceanfront
Parking
Pool
Ocean View
US $660/Night
7 Nights - US $4,621
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
Breakfast- Parking
- Pool
View
US $953/Night
7 Nights - US $6,673
Cottage
- Key West
- ·
- Uptown - Upper Duval
- 0.15 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
- Ocean View
Balcony/Terrace- View
Kitchen
US $563/Night
7 Nights - US $3,942
House
- Key West
- ·
- Historic Seaport
- 0.30 mi to center
10.0Exceptional
(8 Reviews)
7 Bedrooms
8 Baths
16 Guests
Private Pool- Parking
- Pool
- Balcony/Terrace
US $1,797/Night
7 Nights - US $12,578
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
10.0Exceptional
(8 Reviews)
3 Bedrooms
2 Baths
8 Guests
1560 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $456/Night
7 Nights - US $3,193
House
- Key West
- ·
- Truman Annex
- 0.10 mi to center
9.8Exceptional
(68 Reviews)
2 Bedrooms
2 Baths
6 Guests
1527 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $513/Night
7 Nights - US $3,588
New
House
- Key West
- ·
- Historic Seaport
- 0.09 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $557/Night
7 Nights - US $3,900
New
Cottage
- Key West
- ·
- Historic Seaport
- 0.15 mi to center
9.6Exceptional
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
420 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $158/Night
7 Nights - US $1,106
Luxury Places to Stay in Sunset Key
Over 3716+ Luxury Places to Stay in or Near Sunset Key
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Breakfast
- Pool
- Balcony/Terrace
- Kitchen
Unlock the Best Price
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Breakfast
- Pool
- Balcony/Terrace
- Kitchen
Unlock the Best Price
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Breakfast
- Pool
- Balcony/Terrace
- Kitchen
Unlock the Best Price
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Breakfast
- Pool
- Balcony/Terrace
- Kitchen
Unlock the Best Price
Resort
- Key West
- ·
- Truman Annex
- 0.19 mi to center
2 Baths
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
Air Conditioner
Unlock the Best Price
House
- Key West
- ·
- Bahama Village
- 0.08 mi to center
4 Bedrooms
4 Baths
8 Guests
3175.35 ft²
- Parking
- Pool
Spa
Internet
Unlock the Best Price
House
2 Bedrooms
2 Baths
8 Guests
2000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $6,131/Night
7 Nights - US $42,919
House
9.5Exceptional
(2 Reviews)
6 Bedrooms
6 Baths
24 Guests
2400.35 ft²
EV Charge Station- Parking
- Pool
- Balcony/Terrace
US $6,002/Night
7 Nights - US $42,014
House
8 Bedrooms
10 Baths
20 Guests
3702.79 ft²
- Parking
- Pool
- Spa
- Internet
US $5,694/Night
7 Nights - US $39,858
Top-Rated Vacation Rentals with a Pool in Sunset Key
Over 2718+ Top-Rated Vacation Rentals with a Pool in or Near Sunset Key
Hotel
10.0Exceptional
(1010 Reviews)
1 Bath
Hot Tub- Breakfast
- Parking
- Pool
US $258/Night
7 Nights - US $1,807
Condo
- Key West
- ·
- Truman Annex
- 0.20 mi to center
10.0Exceptional
(232 Reviews)
2 Bedrooms
1 Bath
4 Guests
674 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $236/Night
7 Nights - US $1,651
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(218 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $404/Night
7 Nights - US $2,826
House
- Key West
- ·
- Uptown - Upper Duval
- 0.02 mi to center
10.0Exceptional
(204 Reviews)
3 Bedrooms
3 Baths
6 Guests
1154 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,233/Night
7 Nights - US $8,632
House
10.0Exceptional
(195 Reviews)
3 Bedrooms
3 Baths
7 Guests
1855 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,116/Night
7 Nights - US $7,814
House
- Key West
- ·
- Truman Annex
- 0.17 mi to center
10.0Exceptional
(192 Reviews)
2 Bedrooms
2 Baths
4 Guests
1080 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $659/Night
7 Nights - US $4,614
Condo
- Key West
- ·
- Truman Annex
- 0.20 mi to center
10.0Exceptional
(192 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $325/Night
7 Nights - US $2,273
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
House
- Key West
- ·
- Key West Historic District
- 0.12 mi to center
10.0Exceptional
(181 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $1,085/Night
7 Nights - US $7,598
Pet-Friendly Vacation Rentals in Sunset Key
Over 1094+ Pet-Friendly Vacation Rentals in or Near Sunset Key
House
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $677/Night
7 Nights - US $4,742
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
645.83 ft²
- Parking
- Pool
- View
- Air Conditioner
US $1,339/Night
7 Nights - US $9,373
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Internet
US $994/Night
7 Nights - US $6,955
House
- Key West
- ·
- Key West Historic District
- 0.10 mi to center
3 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $666/Night
7 Nights - US $4,662
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
New
House
3 Bedrooms
2 Baths
10 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $237/Night
7 Nights - US $1,660
House
2 Bedrooms
2 Baths
5 Guests
650 ft²
- Oceanfront
- Ocean View
- View
- Kitchen
US $218/Night
7 Nights - US $1,523
Apartment
10.0Exceptional
(97 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $373/Night
7 Nights - US $2,608
Condo
10.0Exceptional
(75 Reviews)
1 Bedroom
1 Bath
4 Guests
731 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $431/Night
7 Nights - US $3,019
Large Vacation Homes & Villas in Sunset Key
Over 364+ Large Vacation Homes & Villas in or Near Sunset Key
Villa
10.0Exceptional
(60 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $568/Night
7 Nights - US $3,977
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
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $316/Night
7 Nights - US $2,213
House
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
12 Guests
2443.41 ft²
- Parking
- Pool
- View
- Air Conditioner
US $2,823/Night
7 Nights - US $19,762
Villa
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $506/Night
7 Nights - US $3,541
Villa
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $443/Night
7 Nights - US $3,098
Villa
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $291/Night
7 Nights - US $2,034
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
10 Guests
780 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $176/Night
7 Nights - US $1,233
Villa
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
350 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $316/Night
7 Nights - US $2,213
Wheelchair Accessible Vacation Homes in Sunset Key
Over 662+ Wheelchair Accessible Vacation Homes in or Near Sunset Key
New
Resort
- Key West
- ·
- Truman Annex
- 0.19 mi to center
10.0Exceptional
(1 Review)
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,748/Night
7 Nights - US $12,235
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- View
- Air Conditioner
US $474/Night
7 Nights - US $3,318
Bed & Breakfast
- Key West
- ·
- Bahama Village
- 0.09 mi to center
9.4Exceptional
(1004 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $201/Night
7 Nights - US $1,410
Hotel
2 Baths
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,819/Night
7 Nights - US $12,734
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Ocean View
- View
- Air Conditioner
US $276/Night
7 Nights - US $1,932
New
Resort
1 Bath
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,332/Night
7 Nights - US $9,325
Condo
10.0Exceptional
(167 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $310/Night
7 Nights - US $2,170
Condo
10.0Exceptional
(162 Reviews)
3 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $490/Night
7 Nights - US $3,429
Condo
10.0Exceptional
(148 Reviews)
2 Bedrooms
2 Baths
6 Guests
1463 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $584/Night
7 Nights - US $4,090
Sunset Key Resorts and Airbnb Homes Under $200
Over 272+ Sunset Key Resorts and Airbnb Homes Under $200
Condo
10.0Exceptional
(31 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $142/Night
7 Nights - US $994
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
710.42 ft²
- Parking
- Pool
- View
- Air Conditioner
US $190/Night
7 Nights - US $1,330
Bed & Breakfast
- Key West
- ·
- Historic Seaport
- 0.16 mi to center
9.8Exceptional
(444 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Breakfast
- Ocean View
- Balcony/Terrace
US $136/Night
7 Nights - US $951
Apartment
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
475 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $139/Night
7 Nights - US $970
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
House
- Key West
- ·
- Truman Annex
- 0.23 mi to center
10.0Exceptional
(24 Reviews)
1 Bedroom
1 Bath
4 Guests
604 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $183/Night
7 Nights - US $1,281
House
- Key West
- ·
- Key West Historic District
- 0.36 mi to center
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
2 Guests
540 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $163/Night
7 Nights - US $1,140
House
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
4 Guests
620 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $165/Night
7 Nights - US $1,158
House
- Key West
- ·
- Key West Historic District
- 0.36 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1140 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $185/Night
7 Nights - US $1,293
Instantly Bookable Vacation Homes in Sunset Key
Over 2353+ Instantly Bookable Vacation Homes in or Near Sunset Key
Cottage
- Key West
- ·
- Historic Seaport
- 0.13 mi to center
9.4Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $640/Night
7 Nights - US $4,477
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1266 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $261/Night
7 Nights - US $1,826
New
Apartment
- Key West
- ·
- Key West Historic District
- 0.15 mi to center
8.0Excellent
(18 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $334/Night
7 Nights - US $2,338
Condo
- Key West
- ·
- Truman Annex
- 0.23 mi to center
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $219/Night
7 Nights - US $1,534
New
Hotel
10.0Exceptional
(2 Reviews)
3 Baths
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $1,374/Night
7 Nights - US $9,616
Hotel
10.0Exceptional
(2 Reviews)
3 Baths
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $802/Night
7 Nights - US $5,615
New
Hotel
10.0Exceptional
(2 Reviews)
2 Baths
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $571/Night
7 Nights - US $4,000
New
Hotel
10.0Exceptional
(1 Review)
6 Baths
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $2,199/Night
7 Nights - US $15,392
Hotel
10.0Exceptional
(1 Review)
4 Baths
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $1,124/Night
7 Nights - US $7,868
Book a Last Minute Place to Stay in Sunset Key
About Sunset Key Vacation Rentals
Explore over 3725 vacation rentals in Sunset Key with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Sunset Key for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Sunset Key. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Sunset Key tailored to your preferences. On average, these rentals offer 784.96 ft² of space, and are priced at an average of US $753 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Sunset Key at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Sunset Key
| Type | Count |
|---|---|
| Vacation Homes | 1914 |
| Holiday Apartments | 523 |
| Cottages | 105 |
| B&B | 43 |
| Villas | 27 |
| Unique Vacation Rentals | 15 |
| Cabin Rentals | 7 |
| Others | 2 |
Use these Quick Filters to Find a Vacation Rental in Sunset Key
★ Pro Tip: Discover Your Ideal Vacation Rental in Sunset Key with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
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 vacation rentals in Sunset Key?
When organizing your trip to Sunset Key, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Sunset Key. Peruse our collection of highly-rated properties and secure your reservation today.
- Almond Tree Inn Hotel - Adults Only
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- 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
- ~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
- Key West Beachfront Luxury 2/2 Condo A212
How many vacation rentals have private pools in Sunset Key?
Uncover 727 vacation rentals boasting private pools near Sunset Key. Explore top-rated RBO homes offering access to a swimming pool:
- Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
- Key West Harbor Inn - Adults Only
- Tropical Oasis in the Truman Annex with a private pool
- Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Which vacation homes or resorts in Sunset Key are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Sunset Key. Enjoy great views, locations and save money with SunSki Resorts.™
- Relaxing Beach Getaway, 2BR Villa, with Onsite Pools, Onsite Parking, Shuttle!
- Somewhere on the beach
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
How many SunSkiResorts vacation rentals or resorts are available in Sunset Key?
Discover the ideal vacation rental in Sunset Key with SunSki Resorts™. We provide an extensive selection of over 3725 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Sunset Key.
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