Sunset Key Vacation Rentals & Ski-in/Ski-out Homes
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(220 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
Parking
Pool
Ocean View
Balcony/Terrace
US $398/Night
7 Nights - US $2,787
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
House
- Key West
- ·
- Truman Annex
- 0.02 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
Child Friendly
US $421/Night
7 Nights - US $2,947
Condo
- Key West
- ·
- Truman Annex
- 0.20 mi to center
10.0Exceptional
(194 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $376/Night
7 Nights - US $2,634
House
- Key West
- ·
- Uptown - Upper Duval
- 0.06 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- View
Pet Friendly- Child Friendly
Security/Safety
US $364/Night
7 Nights - US $2,548
House
- Key West
- ·
- Truman Annex
- 0.17 mi to center
10.0Exceptional
(193 Reviews)
2 Bedrooms
2 Baths
4 Guests
1080 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $787/Night
7 Nights - US $5,512
House
10.0Exceptional
(189 Reviews)
2 Bedrooms
2 Baths
6 Guests
765 ft²
Private Pool- Pool
- Balcony/Terrace
Kitchen
US $872/Night
7 Nights - US $6,106
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(178 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
Oceanfront- Parking
- Pool
- Ocean View
US $197/Night
7 Nights - US $1,380
Condo
10.0Exceptional
(173 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
Hot Tub- Parking
- Pool
US $599/Night
7 Nights - US $4,191
Luxury Places to Stay in Sunset Key
Over 3583+ 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
House
- Key West
- ·
- Bahama Village
- 0.08 mi to center
4 Bedrooms
4 Baths
8 Guests
3175.35 ft²
- Parking
- Pool
Spa- View
Unlock the Best Price
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
- View
US $5,694/Night
7 Nights - US $39,858
Apartment
- Key West
- ·
- Historic Seaport
- 0.23 mi to center
8 Bedrooms
8 Baths
25 Guests
2701.74 ft²
- Child Friendly
- Security/Safety
US $5,686/Night
7 Nights - US $39,799
House
- Key West
- ·
- Bahama Village
- 0.09 mi to center
4 Bedrooms
4 Baths
8 Guests
1679.17 ft²
- Parking
- Pool
- Spa
Internet
US $5,347/Night
7 Nights - US $37,429
Top-Rated Vacation Rentals with a Pool in Sunset Key
Over 2565+ Top-Rated Vacation Rentals with a Pool in or Near Sunset Key
Cottage
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(209 Reviews)
3 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $229/Night
7 Nights - US $1,602
Condo
10.0Exceptional
(171 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $568/Night
7 Nights - US $3,973
Condo
10.0Exceptional
(164 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $491/Night
7 Nights - US $3,438
House
- Key West
- ·
- Uptown - Upper Duval
- 0.10 mi to center
10.0Exceptional
(153 Reviews)
5 Bedrooms
4 Baths
12 Guests
2700 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $1,568/Night
7 Nights - US $10,976
Condo
10.0Exceptional
(152 Reviews)
2 Bedrooms
2 Baths
6 Guests
1463 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $621/Night
7 Nights - US $4,347
House
10.0Exceptional
(144 Reviews)
5 Bedrooms
5 Baths
12 Guests
2651 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,763/Night
7 Nights - US $12,341
Condo
10.0Exceptional
(129 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $600/Night
7 Nights - US $4,197
House
- Key West
- ·
- Key West Historic District
- 0.14 mi to center
10.0Exceptional
(111 Reviews)
1 Bedroom
1 Bath
2 Guests
277 ft²
- Pool
- Balcony/Terrace
- Kitchen
Air Conditioner
US $341/Night
7 Nights - US $2,384
Condo
- Key West
- ·
- Key West Historic District
- 0.38 mi to center
10.0Exceptional
(108 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $379/Night
7 Nights - US $2,653
Pet-Friendly Vacation Rentals in Sunset Key
Over 1068+ Pet-Friendly Vacation Rentals in or Near Sunset Key
Apartment
10.0Exceptional
(99 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $332/Night
7 Nights - US $2,327
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
- Kitchen
US $792/Night
7 Nights - US $5,546
Condo
10.0Exceptional
(76 Reviews)
1 Bedroom
1 Bath
4 Guests
731 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $431/Night
7 Nights - US $3,018
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 $540/Night
7 Nights - US $3,778
Condo
- Key West
- ·
- Uptown - Upper Duval
- 0.12 mi to center
10.0Exceptional
(69 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $744/Night
7 Nights - US $5,205
House
- Key West
- ·
- Uptown - Upper Duval
- 0.05 mi to center
10.0Exceptional
(42 Reviews)
2 Bedrooms
3 Baths
8 Guests
1370 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $672/Night
7 Nights - US $4,707
House
- Key West
- ·
- Uptown - Upper Duval
- 0.09 mi to center
10.0Exceptional
(40 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,321/Night
7 Nights - US $9,246
Condo
10.0Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $400/Night
7 Nights - US $2,802
Large Vacation Homes & Villas in Sunset Key
Over 347+ Large Vacation Homes & Villas in or Near Sunset Key
Villa
10.0Exceptional
(66 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $632/Night
7 Nights - US $4,427
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 $2,492/Night
7 Nights - US $17,441
Boat Rental
3 Bedrooms
2 Baths
10 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $254/Night
7 Nights - US $1,780
Villa
10.0Exceptional
(25 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $312/Night
7 Nights - US $2,185
House
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
12 Guests
2443.41 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $2,823/Night
7 Nights - US $19,762
Villa
10.0Exceptional
(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $503/Night
7 Nights - US $3,520
Villa
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $506/Night
7 Nights - US $3,541
Villa
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $367/Night
7 Nights - US $2,570
House
- Key West
- ·
- Uptown - Upper Duval
- 0.05 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
5 Baths
14 Guests
2571 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,566/Night
7 Nights - US $10,959
Wheelchair Accessible Vacation Homes in Sunset Key
Over 619+ Wheelchair Accessible Vacation Homes in or Near Sunset Key
Condo
10.0Exceptional
(60 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $703/Night
7 Nights - US $4,918
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1151.74 ft²
- Pool
- Balcony/Terrace
- View
- Air Conditioner
US $474/Night
7 Nights - US $3,318
House
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $2,792/Night
7 Nights - US $19,544
Condo
10.0Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $633/Night
7 Nights - US $4,430
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
Condo
10.0Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $568/Night
7 Nights - US $3,974
Condo
10.0Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
1325 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $712/Night
7 Nights - US $4,981
Condo
- Key West
- ·
- Historic Seaport
- 0.21 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1195 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $627/Night
7 Nights - US $4,386
House
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
6 Guests
550 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $664/Night
7 Nights - US $4,648
Sunset Key Resorts and Airbnb Homes Under $200
Over 218+ Sunset Key Resorts and Airbnb Homes Under $200
Apartment
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
475 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $141/Night
7 Nights - US $987
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
House
- Key West
- ·
- Uptown - Upper Duval
- 0.13 mi to center
9.8Exceptional
(548 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,331
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 $198/Night
7 Nights - US $1,387
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
- ·
- 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
- Key West
- ·
- Key West Historic District
- 0.36 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1020 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $191/Night
7 Nights - US $1,339
House
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
4 Guests
620 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $174/Night
7 Nights - US $1,219
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 $195/Night
7 Nights - US $1,368
Instantly Bookable Vacation Homes in Sunset Key
Over 2281+ Instantly Bookable Vacation Homes in or Near Sunset Key
Cottage
- Key West
- ·
- Bahama Village
- 0.13 mi to center
10.0Exceptional
(172 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $555/Night
7 Nights - US $3,887
US $937/Night
7 Nights - US $6,560
House
- Key West
- ·
- Key West Historic District
- 0.12 mi to center
10.0Exceptional
(135 Reviews)
2 Bedrooms
2 Baths
4 Guests
840 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $785/Night
7 Nights - US $5,497
House
- Key West
- ·
- Key West Historic District
- 0.14 mi to center
10.0Exceptional
(107 Reviews)
1 Bedroom
1 Bath
2 Guests
290 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $327/Night
7 Nights - US $2,291
Apartment
- Key West
- ·
- Key West Historic District
- 0.09 mi to center
10.0Exceptional
(93 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Parking
- Pool
- Ocean View
- View
US $791/Night
7 Nights - US $5,540
Apartment
- Key West
- ·
- Key West Historic District
- 0.09 mi to center
10.0Exceptional
(81 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $478/Night
7 Nights - US $3,348
Cottage
- Key West
- ·
- Historic Seaport
- 0.13 mi to center
10.0Exceptional
(80 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $802/Night
7 Nights - US $5,611
House
10.0Exceptional
(79 Reviews)
2 Bedrooms
1 Bath
4 Guests
1080 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $646/Night
7 Nights - US $4,520
Apartment
- Key West
- ·
- Key West Historic District
- 0.09 mi to center
10.0Exceptional
(66 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $488/Night
7 Nights - US $3,418
Book a Last Minute Place to Stay in Sunset Key
About Sunset Key Vacation Rentals
Explore over 3592 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 762.29 ft² of space, and are priced at an average of US $767 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 | 1866 |
| Holiday Apartments | 526 |
| Cottages | 99 |
| B&B | 36 |
| Villas | 26 |
| Unique Vacation Rentals | 16 |
| 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.
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Walkable Cottage w/Pool Access in Key West!
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- Everything Key West has to offer @ Mango Cottage
- Central Condo w/Deck & Pool Access in Key West!
- Key West Beachfront Luxury 2/2 Condo A212
- Heart of Downtown Key West Cottage With Off-Street Parking
- Your Condo by the Beach with Ocean View
- *FOLLOW THE SUN* Ocean Condo/Pool & Tennis + Last Key White Glove Service.
How many vacation rentals have private pools in Sunset Key?
Uncover 687 vacation rentals boasting private pools near Sunset Key. Explore top-rated RBO homes offering access to a swimming pool:
- Tropical Oasis in the Truman Annex with a private pool
- Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
- Furnished 2BR Condo – Gated Old Town Key West – Monthly/Seasonal – Walk to Duval
- ~ INN COGNEATO ~Experience island life in a private oasis with heated pool.
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.™
- FLEMING-O (Flamingo) Cottage is the perfect getaway
- Somewhere on the beach
- Duval Dream Loft by Brightwild Right on Duval
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 3592 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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