3804+ Perfect Pickle Stays with Nearby Pickleball Facilities |
Sunset Key pickleball Stays, Resort Rentals, & Homes
New
House
2 Bedrooms
2 Baths
4 Guests
1099 ft²
Oceanfront
Pool
Ocean View
Balcony/Terrace
US $330/Night
7 Nights - US $2,312
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
Cottage
- Key West
- ·
- Uptown - Upper Duval
- 0.15 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
- Ocean View
- Balcony/Terrace
- View
Pet Friendly
US $563/Night
7 Nights - US $3,942
Condo
9.8Exceptional
(227 Reviews)
2 Bedrooms
2 Baths
6 Guests
1469 ft²
- Oceanfront
Hot Tub
Spa- Pool
US $452/Night
7 Nights - US $3,162
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
Condo
- Key West
- ·
- Uptown - Upper Duval
- 0.13 mi to center
9.8Exceptional
(96 Reviews)
2 Bedrooms
2 Baths
8 Guests
1500 ft²
Fireplace/Heating- Ocean View
- Balcony/Terrace
- View
US $726/Night
7 Nights - US $5,079
New
House
- Key West
- ·
- Key West Historic District
- 0.37 mi to center
9.8Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
960 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
US $216/Night
7 Nights - US $1,513
Condo
9.6Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1175 ft²
- Hot Tub
- Pool
- Balcony/Terrace
Kitchen
US $150/Night
7 Nights - US $1,048
Condo
9.4Exceptional
(59 Reviews)
2 Bedrooms
3 Baths
6 Guests
1905 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $613/Night
7 Nights - US $4,289
Luxury Places to Stay in Sunset Key
Over 3795+ Luxury Places to Stay in or Near Sunset Key
House
9.8Exceptional
(109 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $2,471/Night
7 Nights - US $17,295
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
4 Baths
10 Guests
2400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,596/Night
7 Nights - US $11,175
Villa
10.0Exceptional
(1 Review)
3 Bedrooms
4 Baths
7 Guests
2800 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,048/Night
7 Nights - US $7,337
House
9.6Exceptional
(29 Reviews)
3 Bedrooms
2 Baths
6 Guests
1938 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $831/Night
7 Nights - US $5,814
House
9.4Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $821/Night
7 Nights - US $5,749
Condo
9.8Exceptional
(53 Reviews)
4 Bedrooms
3 Baths
8 Guests
2038 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $779/Night
7 Nights - US $5,452
Condo
9.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $768/Night
7 Nights - US $5,378
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
7 Guests
1650 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $739/Night
7 Nights - US $5,170
Condo
9.2Exceptional
(56 Reviews)
2 Bedrooms
2 Baths
6 Guests
1186 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $653/Night
7 Nights - US $4,573
Top-Rated Villas with a Pool in Sunset Key
Over 2797+ Top-Rated Private Villas with a Pool in or Near Sunset Key
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
1420 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $391/Night
7 Nights - US $2,740
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
1440 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $385/Night
7 Nights - US $2,698
Condo
9.4Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1099 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $521/Night
7 Nights - US $3,648
House
3 Bedrooms
3 Baths
6 Guests
1950 ft²
- Pool
- Balcony/Terrace
- Kitchen
Air Conditioner
US $616/Night
7 Nights - US $4,309
Condo
3 Bedrooms
4 Baths
8 Guests
1876 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $440/Night
7 Nights - US $3,080
House
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $398/Night
7 Nights - US $2,787
House
2 Bedrooms
2 Baths
4 Guests
1092 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $369/Night
7 Nights - US $2,585
Hotel
10.0Exceptional
(1005 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $290/Night
7 Nights - US $2,027
Cottage
10.0Exceptional
(238 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $773/Night
7 Nights - US $5,412
Pet-Friendly Villas in Sunset Key
Over 1113+ Pet-Friendly Private Villas in or Near Sunset Key
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
- 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
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
US $731/Night
7 Nights - US $5,115
New
House
3 Bedrooms
3 Baths
6 Guests
1615 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,038/Night
7 Nights - US $7,267
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
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 $421/Night
7 Nights - US $2,947
New
House
3 Bedrooms
3 Baths
5 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $239/Night
7 Nights - US $1,675
Apartment
10.0Exceptional
(96 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
Internet
US $357/Night
7 Nights - US $2,502
Large Private Villas in Sunset Key
Over 376+ Large Villas in or Near Sunset Key for Groups and Families
Villa
10.0Exceptional
(58 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $618/Night
7 Nights - US $4,323
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
(45 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $614/Night
7 Nights - US $4,299
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
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $325/Night
7 Nights - US $2,276
Villa
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $379/Night
7 Nights - US $2,656
Villa
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $379/Night
7 Nights - US $2,656
Villa
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $291/Night
7 Nights - US $2,034
Villa
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
350 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $316/Night
7 Nights - US $2,213
Wheelchair Accessible Holiday Homes in Sunset Key
Over 683+ Wheelchair Accessible Villas and Holiday Homes in or Near Sunset Key
Condo
10.0Exceptional
(168 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $555/Night
7 Nights - US $3,882
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
Bed & Breakfast
- Key West
- ·
- Bahama Village
- 0.09 mi to center
9.4Exceptional
(1002 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Parking
US $224/Night
7 Nights - US $1,567
Condo
10.0Exceptional
(166 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $307/Night
7 Nights - US $2,149
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
(161 Reviews)
3 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
US $515/Night
7 Nights - US $3,603
Condo
10.0Exceptional
(145 Reviews)
2 Bedrooms
2 Baths
6 Guests
1463 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $489/Night
7 Nights - US $3,420
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
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
Sunset Key Villas, Airbnb and Holiday Homes Under $200
Over 283+ Sunset Key Private Villas, Airbnb 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
House
9.6Exceptional
(1001 Reviews)
1 Bedroom
1 Bath
- Ocean View
- Balcony/Terrace
- View
- Breakfast
US $173/Night
7 Nights - US $1,210
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
Condo
10.0Exceptional
(31 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $141/Night
7 Nights - US $984
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
Apartment
10.0Exceptional
(27 Reviews)
1 Bedroom
1 Bath
2 Guests
475 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $140/Night
7 Nights - US $980
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
Instantly Bookable Villa Rentals in Sunset Key
Over 2419+ Instantly Bookable Private Villas in or Near Sunset Key
Hotel
3 Baths
- Pool
- Kitchen
- Parking
- Air Conditioner
US $913/Night
7 Nights - US $6,393
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
Condo
- Key West
- ·
- Truman Annex
- 0.20 mi to center
10.0Exceptional
(232 Reviews)
2 Bedrooms
1 Bath
4 Guests
674 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $236/Night
7 Nights - US $1,652
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 $587/Night
7 Nights - US $4,106
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 $274/Night
7 Nights - US $1,918
House
- Key West
- ·
- Bahama Village
- 0.11 mi to center
10.0Exceptional
(162 Reviews)
2 Bedrooms
2 Baths
4 Guests
950 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $439/Night
7 Nights - US $3,070
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 $781/Night
7 Nights - US $5,465
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
Book a Last Minute Place to Stay in Sunset Key
About Sunset Key Vacation Rentals
Discover over 3804 amazing vacation rental options in Sunset Key with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Sunset Key.
Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 792.44 ft², with prices averaging US $767 per night.
With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Sunset Key.
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Top Pickleball-Ready Accommodation Types in Sunset Key
| Type | Count |
|---|---|
| Vacation Homes | 1950 |
| Holiday Apartments | 531 |
| Cottages | 112 |
| Villas | 31 |
Use these Quick Filters to Find a Vacation Rental in Sunset Key
★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Sunset Key with PickleTrip™.
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, resorts, and hotels in Sunset Key with Courts?
Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Sunset Key. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Sunset Key!
- 3 bedroom with living room and sitting room and a pool just 2 blocks from Higgs beach
- 4-bedroom resort style home in awesome Key West with large pool and private deck
- Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
- BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/Pool!
- Bahama Village Sanctuary - Family & Dog Friendly
- ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/Pool, Fitness Area & Beach!
- ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
- A Duval Street Oasis with balcony overlooking Duval
- GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/Pool and Ocean Views!
- Old Town Key West classic with private saltwater pool & enclosed patio- by shops
How many pickleball-ready properties have private pools in Sunset Key?
Discover 758 accommodations with private or nearby pickleball courts in Sunset Key. Some of the best destinations to stay and play pickleball are:
- 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 rentals, resorts, or hotels in Sunset Key is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Sunset Key? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Somewhere on the beach
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
How many PickleTrip vacation rentals or resorts are available in Sunset Key?
PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 3804 properties listed in Sunset Key in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.
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