3758+ Vacation Home Rentals in Sunset Key |
Sunset Key Vacation Rentals & Ski-in/Ski-out Homes
10.0
Exceptional
(2 Reviews)
- Key West
- Uptown - Upper Duval
- 0.09 mi to center
1222 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $1,451/Night
For 7 Nights US $10,156
10.0
Exceptional
(4 Reviews)
2002.09 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- View
- Breakfast
- Parking
US $953/Night
For 7 Nights US $6,673
10.0
Exceptional
(6 Reviews)
- Key West
- Uptown - Upper Duval
- 0.15 mi to center
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Ocean View
- Balcony/Terrace
- View
US $916/Night
For 7 Nights US $6,413
New
- Key West
- Uptown - Upper Duval
- 0.03 mi to center
1618 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $1,524/Night
For 7 Nights US $10,666
10.0
Exceptional
(3 Reviews)
1496.18 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Pool
- View
- Breakfast
US $891/Night
For 7 Nights US $6,236
New
1750 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $1,220/Night
For 7 Nights US $8,542
New
3500 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $999/Night
For 7 Nights US $6,993
New
6 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $956/Night
For 7 Nights US $6,694
New
- Key West
- Historic Seaport
- 0.15 mi to center
3000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $623/Night
For 7 Nights US $4,363
Luxury Places to Stay in Sunset Key
Over 3749+ Luxury Places to Stay in or Near Sunset Key
Unlock the Best Price
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New
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
Unlock the Best Price
New
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
Unlock the Best Price
New
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
Unlock the Best Price
Unlock the Best Price
New
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
Unlock the Best Price
New
- Key West
- Uptown - Upper Duval
- 0.07 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
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Top-Rated Vacation Rentals with a Pool in Sunset Key
Over 2752+ Top-Rated Vacation Rentals with a Pool in or Near Sunset Key
10.0
Exceptional
(1000 Reviews)
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Balcony/Terrace
US $367/Night
For 7 Nights US $2,570
10.0
Exceptional
(236 Reviews)
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Private Pool
- Oceanfront
- Fireplace/Heating
US $954/Night
For 7 Nights US $6,680
10.0
Exceptional
(232 Reviews)
- Key West
- Truman Annex
- 0.20 mi to center
674 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $246/Night
For 7 Nights US $1,721
10.0
Exceptional
(229 Reviews)
- Key West
- Uptown - Upper Duval
- 0.16 mi to center
1440 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Private Pool
- Pool
- Balcony/Terrace
US $1,156/Night
For 7 Nights US $8,094
10.0
Exceptional
(218 Reviews)
- Key West
- Truman Annex
- 0.21 mi to center
700 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $321/Night
For 7 Nights US $2,250
10.0
Exceptional
(209 Reviews)
- Key West
- Truman Annex
- 0.16 mi to center
1250 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Pool
US $338/Night
For 7 Nights US $2,363
10.0
Exceptional
(205 Reviews)
1875 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $2,592/Night
For 7 Nights US $18,141
10.0
Exceptional
(201 Reviews)
- Key West
- Uptown - Upper Duval
- 0.02 mi to center
1154 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $1,215/Night
For 7 Nights US $8,505
10.0
Exceptional
(193 Reviews)
1855 ft²
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $1,668/Night
For 7 Nights US $11,673
Pet-Friendly Vacation Rentals in Sunset Key
Over 1072+ Pet-Friendly Vacation Rentals in or Near Sunset Key
New
1588 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $376/Night
For 7 Nights US $2,634
10.0
Exceptional
(2 Reviews)
785.77 ft²
6 Guests
2 Bedrooms
1 Bathroom
House
- Pet Friendly
- Parking
- Internet
US $830/Night
For 7 Nights US $5,809
10.0
Exceptional
(1 Review)
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Balcony/Terrace
- Pet Friendly
US $944/Night
For 7 Nights US $6,610
New
650 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
US $363/Night
For 7 Nights US $2,543
10.0
Exceptional
(2 Reviews)
- Key West
- Uptown - Upper Duval
- 0.10 mi to center
398.26 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Internet
- Child Friendly
US $370/Night
For 7 Nights US $2,587
New
1533 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Pet Friendly
US $251/Night
For 7 Nights US $1,759
10.0
Exceptional
(96 Reviews)
300 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
US $380/Night
For 7 Nights US $2,662
10.0
Exceptional
(69 Reviews)
731 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Pool
- Balcony/Terrace
- Pet Friendly
US $529/Night
For 7 Nights US $3,704
10.0
Exceptional
(61 Reviews)
- Key West
- Uptown - Upper Duval
- 0.12 mi to center
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
US $625/Night
For 7 Nights US $4,373
Large Vacation Homes & Villas in Sunset Key
Over 376+ Large Vacation Homes & Villas in or Near Sunset Key
10.0
Exceptional
(55 Reviews)
850 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $941/Night
For 7 Nights US $6,584
10.0
Exceptional
(1 Review)
- Key West
- Key West Historic District
- 0.15 mi to center
2045.14 ft²
14 Guests
1 Bedroom
4 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Child Friendly
- Barbecue/Outdoor Cooking
US $875/Night
For 7 Nights US $6,125
10.0
Exceptional
(44 Reviews)
850 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $758/Night
For 7 Nights US $5,308
9.7
Exceptional
(379 Reviews)
522.82 ft²
28 Guests
9 Bedrooms
9 Bathrooms
Free Cancellation
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $369/Night
For 7 Nights US $2,583
10.0
Exceptional
(23 Reviews)
350 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $610/Night
For 7 Nights US $4,268
10.0
Exceptional
(17 Reviews)
550 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $506/Night
For 7 Nights US $3,541
10.0
Exceptional
(8 Reviews)
500 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $503/Night
For 7 Nights US $3,520
10.0
Exceptional
(1 Review)
350 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $569/Night
For 7 Nights US $3,984
10.0
Exceptional
(1 Review)
200 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $438/Night
For 7 Nights US $3,063
Wheelchair Accessible Vacation Homes in Sunset Key
Over 693+ Wheelchair Accessible Vacation Homes in or Near Sunset Key
10.0
Exceptional
(166 Reviews)
1357 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Spa
US $639/Night
For 7 Nights US $4,472
10.0
Exceptional
(1 Review)
6 Guests
2 Bedrooms
1 Bathroom
Apartment
- Ocean View
- View
- Pet Friendly
US $276/Night
For 7 Nights US $1,932
9.4
Exceptional
(1004 Reviews)
- Key West
- Bahama Village
- 0.09 mi to center
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Pool
- Balcony/Terrace
- Breakfast
US $413/Night
For 7 Nights US $2,894
10.0
Exceptional
(164 Reviews)
750 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $322/Night
For 7 Nights US $2,257
9.5
Exceptional
(508 Reviews)
419.79 ft²
6 Guests
3 Bathrooms
Resort
- Oceanfront
- Fireplace/Heating
- Pool
US $1,688/Night
For 7 Nights US $11,816
10.0
Exceptional
(159 Reviews)
1357 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Spa
US $620/Night
For 7 Nights US $4,342
10.0
Exceptional
(143 Reviews)
1463 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $509/Night
For 7 Nights US $3,560
10.0
Exceptional
(125 Reviews)
1357 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Spa
US $685/Night
For 7 Nights US $4,792
10.0
Exceptional
(59 Reviews)
1350 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Spa
- Pool
US $734/Night
For 7 Nights US $5,136
Sunset Key Resorts and Airbnb Homes Under $200
Over 234+ Sunset Key Resorts and Airbnb Homes Under $200
New
405 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $181/Night
For 7 Nights US $1,266
10.0
Exceptional
(1 Review)
710.42 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pool
- View
- Pet Friendly
US $190/Night
For 7 Nights US $1,330
New
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Child Friendly
US $175/Night
For 7 Nights US $1,222
New
622 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $155/Night
For 7 Nights US $1,082
9.0
Exceptional
(1414 Reviews)
235.27 ft²
18 Guests
11 Bedrooms
7 Bathrooms
Bed & Breakfast
- Balcony/Terrace
- View
- Air Conditioner
US $199/Night
For 7 Nights US $1,393
10.0
Exceptional
(45 Reviews)
- Key West
- Bahama Village
- 0.11 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $191/Night
For 7 Nights US $1,337
10.0
Exceptional
(31 Reviews)
650 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $141/Night
For 7 Nights US $984
10.0
Exceptional
(26 Reviews)
475 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $145/Night
For 7 Nights US $1,015
10.0
Exceptional
(23 Reviews)
- Key West
- Truman Annex
- 0.17 mi to center
513 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $193/Night
For 7 Nights US $1,348
Instantly Bookable Vacation Homes in Sunset Key
Over 2397+ Instantly Bookable Vacation Homes in or Near Sunset Key
New
- Key West
- Key West Historic District
- 0.38 mi to center
1350 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Pool
- Kitchen
- Air Conditioner
US $348/Night
For 7 Nights US $2,437
10.0
Exceptional
(6 Reviews)
1266 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $261/Night
For 7 Nights US $1,826
10.0
Exceptional
(192 Reviews)
- Key West
- Truman Annex
- 0.20 mi to center
700 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $276/Night
For 7 Nights US $1,931
10.0
Exceptional
(186 Reviews)
- Key West
- Truman Annex
- 0.17 mi to center
1080 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $812/Night
For 7 Nights US $5,681
10.0
Exceptional
(178 Reviews)
- Key West
- Truman Annex
- 0.21 mi to center
800 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $213/Night
For 7 Nights US $1,488
10.0
Exceptional
(162 Reviews)
- Key West
- Bahama Village
- 0.11 mi to center
950 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $439/Night
For 7 Nights US $3,070
10.0
Exceptional
(152 Reviews)
- Key West
- Historic Seaport
- 0.22 mi to center
800 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Hot Tub
- Ocean View
US $919/Night
For 7 Nights US $6,431
10.0
Exceptional
(146 Reviews)
- Key West
- Bahama Village
- 0.13 mi to center
3 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Parking
US $374/Night
For 7 Nights US $2,615
10.0
Exceptional
(135 Reviews)
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $798/Night
For 7 Nights US $5,583
Book a Last Minute Place to Stay in Sunset Key
About Sunset Key Vacation Rentals
Explore over 3758 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 786.34 ft² of space, and are priced at an average of US $858 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 | 1929 |
| Holiday Apartments | 511 |
| Cottages | 111 |
| B&B | 44 |
| Villas | 31 |
| Unique Vacation Rentals | 15 |
| Cabin Rentals | 7 |
| Others | 1 |
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
- Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
- 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!
- 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
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
How many vacation rentals have private pools in Sunset Key?
Uncover 737 vacation rentals boasting private pools near Sunset Key. Explore top-rated RBO homes offering access to a swimming pool:
- 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 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.™
- Everything Key West has to offer @ Mango Cottage
- A Place In Paradise by AvantStay Key West Walkable w Shared Pool Month Long Stays Only
- 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 3758 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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