Best Vacation Homes in Sunset Key
Condo
10.0(219 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
Oceanfront
Parking
Pool
Ocean View
CA $464/Night
7 Nights - CA $3,251
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
Breakfast- Parking
- Pool
View
CA $1,330/Night
7 Nights - CA $9,313
House
10.0(5 Reviews)
1 Bedroom
1 Bath
- Parking
- Pool
Balcony/Terrace
Kitchen
CA $588/Night
7 Nights - CA $4,113
House
10.0(193 Reviews)
2 Bedrooms
2 Baths
4 Guests
1080 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $917/Night
7 Nights - CA $6,420
House
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
Pet Friendly
Child Friendly
Security/Safety
CA $508/Night
7 Nights - CA $3,556
Condo
10.0(192 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $463/Night
7 Nights - CA $3,244
House
10.0(187 Reviews)
2 Bedrooms
2 Baths
6 Guests
765 ft²
Private Pool- Pool
- Balcony/Terrace
- Kitchen
CA $913/Night
7 Nights - CA $6,388
Condo
10.0(172 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
Hot Tub- Parking
- Pool
CA $929/Night
7 Nights - CA $6,503
Sunset Key Luxury Rentals
House
4 Bedrooms
4 Baths
8 Guests
3175.35 ft²
- Parking
- Pool
Spa
Internet
Unlock the Best Price
House
9.5(2 Reviews)
6 Bedrooms
6 Baths
24 Guests
2400.35 ft²
EV Charge Station- Parking
- Pool
- Balcony/Terrace
CA $8,377/Night
7 Nights - CA $58,638
House
8 Bedrooms
10 Baths
20 Guests
3702.79 ft²
- Parking
- Pool
- Spa
- Internet
CA $7,947/Night
7 Nights - CA $55,629
Apartment
8 Bedrooms
8 Baths
25 Guests
2701.74 ft²
- Child Friendly
- Security/Safety
CA $7,935/Night
7 Nights - CA $55,547
House
4 Bedrooms
4 Baths
8 Guests
1679.17 ft²
- Parking
- Pool
- Spa
- Internet
CA $7,463/Night
7 Nights - CA $52,239
House
10.0(13 Reviews)
11 Bedrooms
5 Baths
20 Guests
5000 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $7,253/Night
7 Nights - CA $50,768
CA $7,035/Night
7 Nights - CA $49,243
House
8 Bedrooms
5 Baths
20 Guests
150.69 ft²
- Oceanfront
- Hot Tub
- Breakfast
- EV Charge Station
CA $6,497/Night
7 Nights - CA $45,478
Sunset Key Pet Friendly Vacation Rentals
Apartment
10.0(98 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Kitchen
Air Conditioner- Internet
- Pet Friendly
CA $438/Night
7 Nights - CA $3,066
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
645.83 ft²
- Parking
- Pool
- View
- Air Conditioner
CA $1,869/Night
7 Nights - CA $13,082
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Internet
CA $1,016/Night
7 Nights - CA $7,110
Condo
10.0(75 Reviews)
1 Bedroom
1 Bath
4 Guests
731 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $578/Night
7 Nights - CA $4,049
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
785.77 ft²
- Pet Friendly
- Child Friendly
- Security/Safety
CA $753/Night
7 Nights - CA $5,273
Condo
10.0(66 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $717/Night
7 Nights - CA $5,019
House
10.0(42 Reviews)
2 Bedrooms
3 Baths
8 Guests
1370 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
CA $997/Night
7 Nights - CA $6,980
House
10.0(39 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $1,567/Night
7 Nights - CA $10,970
Sunset Key Large Vacation Homes
Villa
10.0(60 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $759/Night
7 Nights - CA $5,311
House
10.0(3 Reviews)
4 Bedrooms
4 Baths
12 Guests
2346.53 ft²
- Internet
- Child Friendly
Laundry- Security/Safety
CA $3,759/Night
7 Nights - CA $26,314
Villa
10.0(24 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $404/Night
7 Nights - CA $2,829
House
10.0(1 Review)
4 Bedrooms
4 Baths
12 Guests
2443.41 ft²
- Parking
- Pool
- View
- Air Conditioner
CA $3,940/Night
7 Nights - CA $27,582
Villa
10.0(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
CA $529/Night
7 Nights - CA $3,707
Villa
10.0(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
CA $493/Night
7 Nights - CA $3,447
Villa
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
CA $350/Night
7 Nights - CA $2,451
House
10.0(1 Review)
2 Bedrooms
5 Baths
14 Guests
2571 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $2,131/Night
7 Nights - CA $14,920
Why Choose Rent By Owner for your Sunset Key Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Sunset Key
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation in Sunset Key ensures you enjoy the region’s beautiful climate and vibrant atmosphere at its best, making your stay truly memorable.
Peak Season Highlights
February to April
During these months, you'll experience the warm, inviting weather ideal for enjoying the stunning surroundings of this destination. Expect lively activities and a vibrant atmosphere, making it perfect for a memorable vacation.
Average Temperature Daytime: around 75-85°F - Nighttime: about 65-75°F
December to January
This time of year attracts visitors seeking escape from colder climates, bringing pleasant temperatures and festive holiday events to the area. It's an excellent season for relaxing in your preferred accommodation while soaking up the sun.
Average Temperature Daytime: approximately 70-80°F - Nighttime: roughly 60-70°F
Off-Season Highlights
May to June
As the region transitions into summer, the early months offer slightly cooler conditions and fewer crowds, providing a more peaceful atmosphere for your stay.
Average Temperature Daytime: around 80-88°F - Nighttime: about 70-77°F
September to November
Following the busy summer months, the shoulder season presents more relaxed travel plans with comfortable weather, making it an ideal period for exploring the area without the peak season crowds.
Average Temperature Daytime: approximately 78-85°F - Nighttime: roughly 68-75°F
Weekly Weather Forecast for Sunset Key
How to Book Your Sunset Key Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to private outdoor pools or swimming areas to relax in the sun.
- Take advantage of spacious outdoor patios or decks for dining and entertaining.
- Benefit from well-maintained BBQ grills for outdoor cooking experiences.
- Relax on beautifully landscaped gardens or lush lawns surrounding your rental.
- Make use of shaded pergolas or gazebos ideal for lounging outdoors.
- Explore nearby sandy beaches and water activities available to guests.
- Utilize outdoor showers or rinse stations for easy clean-up after beach days.
Top Attractions Around Sunset Key
What attractions are nearby?
While staying in this scenic area, you can enjoy a variety of nearby activities such as relaxing on pristine beaches, exploring vibrant local marine life through snorkeling and kayaking, or taking leisurely strolls along charming waterfront pathways that showcase the region's natural beauty.
Family Activities
- Snorkeling Adventures: Explore the vibrant marine life just off the coast, making it a perfect family activity while staying in this island destination.
- Beach Relaxation and Picnics: Spend quality time on the soft sands with water views, enjoying a family picnic in the tranquil surroundings of this island haven.
- Sunset Watching: Experience breathtaking sunsets together from the shores or your rental’s balcony, creating unforgettable family memories.
- Kayaking and Paddleboarding: Rent gear to paddle along the calm waters, ideal for young children and beginners seeking outdoor fun in this key region.
Adult Activities
- Sunset Cruises: Embark on an evening cruise to witness breathtaking sunsets over the tranquil waters surrounding this island paradise.
- Snorkeling Adventures: Explore vibrant coral reefs and marine life just off the coast, offering a memorable underwater experience in the area.
- Relaxing Beach Days: Spend your days lounging on pristine beaches, soaking up the sun while enjoying the serene atmosphere of this destination.
- Dining Experiences: Savor fresh seafood and regional delicacies at waterfront restaurants that highlight the region's culinary charm.
Sunset Key Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Beach Days Early: Take advantage of the tranquil beaches by arriving early to secure your spot and enjoy peaceful mornings along the coastline.
- Explore Local Dining Options: Savor the region’s fresh seafood and local flavors by trying out nearby eateries that showcase authentic culinary delights.
- Make Use of Water Activities: Engage in water-based adventures like kayaking or paddleboarding to fully immerse yourself in the vibrant marine environment here.
- Choose a Prime Location: Select a vacation rental positioned close to key attractions and calm beaches for maximum relaxation and convenience during your stay.
Transportation Options
- Ferry Service: You can enjoy a scenic boat ride from Key West to this island sanctuary, offering a convenient and picturesque transportation option for your stay.
- Private Boat Charters: For a personalized experience, charter a boat to reach the area directly, providing flexibility and a luxurious way to explore the region.
- Bike Rentals: Exploring by bike allows you to traverse the island comfortably while taking in the serene surroundings of this destination.
- Walking Access: The compact size of the area makes walking a practical and enjoyable way to navigate between your vacation rental and nearby spots.
Local Customs Options
- Respect for the Local Fishing Traditions: When visiting here, it’s customary to honor the region’s rich fishing heritage by practicing sustainable practices and respecting local fishing regulations.
- Greeting with Courteous Hospitality: Warm welcomes and friendly gestures are a valued part of the customs on this destination, reflecting the area's laid-back and welcoming atmosphere.
- Celebrating Island Festivals: Participation in community celebrations and festivals showcases the region's vibrant culture, inviting visitors to engage respectfully and observe local traditions.
- Environmental Respect and Preservation: It is important to follow guidelines that help preserve the pristine beauty of the area, including proper waste disposal and mindful use of natural resources.
Frequently Asked Questions About Sunset Key?
1. What are the top vacation rentals in Sunset Key?
There are a lot of options in Sunset Key. If you plan on staying in the Sunset Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sunset Key:
- Almond Tree Inn Hotel - Adults Only
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Walkable Cottage w/Pool Access in Key West!
- 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
2. How many vacation rentals have private pools in Sunset Key?
There are 710 vacation rentals with private pools near Sunset Key. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Sunset Key are best for families?
If you are looking for a family-friendly vacation home in Sunset Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sunset Key:
4. How many Rentbyowner vacation rentals are available in Sunset Key?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 3674 in the Sunset Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Sunset Key.
5. What is the cancellation policy for vacation rentals in Sunset Key, Key West?
Cancellation policies vary depending on the property owner or manager. To ensure you understand the specific rules and any applicable fees, please review the listing details carefully or contact the host directly before confirming your reservation.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or taxes may apply and are detailed in each listing. It’s recommended to read the full rental description or reach out to the owner to clarify any extra costs before booking.
7. What amenities are typically included with vacation rentals in this region?
Most properties offer amenities like Wi-Fi, fully equipped kitchens, and outdoor spaces. For specific features such as pools or boat docks, be sure to check each listing directly or contact the owner for complete details.
8. How do I confirm the availability of a vacation rental on my preferred dates?
Availability updates are maintained in real-time on the booking platform. To secure your stay, simply select your dates and proceed with the reservation process or contact the property owner to confirm availability.
9. What steps should I take if I encounter issues during my stay?
In case of problems, it is best to contact the property owner or the local support team listed on your booking confirmation. They can assist with resolving issues promptly and ensuring a smooth experience during your time here.
Sunset Key Top Rated Vacation Rentals
CA $366/Night
7 Nights - CA $2,562
New
Cottage
10.0(209 Reviews)
3 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $315/Night
7 Nights - CA $2,205
House
10.0(204 Reviews)
3 Bedrooms
3 Baths
6 Guests
1154 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,824/Night
7 Nights - CA $12,768
House
10.0(195 Reviews)
3 Bedrooms
3 Baths
7 Guests
1855 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,549/Night
7 Nights - CA $10,842
House
10.0(181 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Kitchen
CA $1,617/Night
7 Nights - CA $11,320
Condo
10.0(167 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $431/Night
7 Nights - CA $3,015
Condo
10.0(164 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $693/Night
7 Nights - CA $4,847
House
10.0(152 Reviews)
5 Bedrooms
4 Baths
12 Guests
2700 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $2,277/Night
7 Nights - CA $15,942
