Vacation Rentals with Pool in Sunset Key, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Sunset Key

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1469 Best Vacation Rentals with Pool in Sunset Key (Starting from $387)

Ocean Key Resort & Spa, a Noble House Resort
Ocean Key Resort & Spa, a Noble House Resort
Resort
Key West, FL, USA
0.7k from Sunset Key center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, 4-star, Lodgings, Jacuzzis

97 Bedrooms46 Guests
8.7

Fabulous

116 reviews

$578
Average price / night
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Key West Sunset Serenade - w Pool & Beach Access
Key West Sunset Serenade - w Pool & Beach Access
House
Key West, FL, 33040, United States
0.0k from Sunset Key center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
New to Booking
$494
Average price / night
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Pier House Resort & Spa
Pier House Resort & Spa
Resort
Key West, FL, USA
0.8k from Sunset Key center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 4-star, Lodgings

140 Bedrooms62 Guests
8.3

Very Good

664 reviews

$534
Average price / night
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Villa Porta del Sole - 3BR Sunset Key Villa with Private Pool, Direct Beach Access and Sunset Ocean View!
Villa Porta del Sole - 3BR Sunset Key Villa with Private Pool, Direct Beach Access and Sunset Ocean View!
House
Key West, FL, 33040, United States
0.1k from Sunset Key center

AC, Barbecue, Dryer, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1102
Average price / night
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Opal Key Resort & Marina
Opal Key Resort & Marina
Resort
Key West, FL, USA
0.8k from Sunset Key center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Hot tubs

188 Bedrooms106 Guests
8.6

Fabulous

1178 reviews

$716
Average price / night
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Modern Luxury Meets Island Privacy: Executive Villa on Exclusive Sunset Key
Modern Luxury Meets Island Privacy: Executive Villa on Exclusive Sunset Key
Villa
Key West, FL, 33040, United States
0.4k from Sunset Key center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms5 Guests
New to Booking
$530
Average price / night
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Harborside Harmony by Last Key Realty
Harborside Harmony by Last Key Realty
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$959
Average price / night
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Ocean Key Resort - A Noble House Resort
Ocean Key Resort - A Noble House Resort
Resort
Zero Duval St., Key West, FL, 33040, United States
0.7k from Sunset Key center

AC, Balcony, Bar, Breakfast Available, Business Services, Crib, Elevator, Fitness Equipment, Frontdesk 24 Hour

9.2

Superb

1002 reviews

$592
Average price / night
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Old Town Oasis by Last Key Realty
Old Town Oasis by Last Key Realty
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms6 Guests
8.0

Good

1 reviews

$497
Average price / night
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Feather Queen at Custom House Inn | Two Vibrant Suites!
Feather Queen at Custom House Inn | Two Vibrant Suites!
Apartment
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Dryer, Free Parking, Internet, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1074
Average price / night
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Hyatt Centric Key West Resort & Spa
Hyatt Centric Key West Resort & Spa
Resort
Key West, FL, USA
0.9k from Sunset Key center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 4-star, Lodgings

118 Bedrooms30 Guests
8.2

Very Good

545 reviews

$387
Average price / night
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2-bedroom condo in the heart of Key West- private beach & pool, tiki bar on-site
2-bedroom condo in the heart of Key West- private beach & pool, tiki bar on-site
Condo
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$652
Average price / night
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Last Minute
Last Minute
House
Key West, FL, USA
0.9k from Sunset Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

3 Bedrooms6 Guests
8.0

Good

2 reviews

$1115
Average price / night
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Sunset at Harbour Place
Sunset at Harbour Place
Apartment
Sunset Key, Key West, Florida, USA
0.9k from Sunset Key center

Apartments, Accommodations, Pools, Lodgings, Places to stay, Accessible hotels

2 Bedrooms6 Guests
7.0

Good

1 reviews

$786
Average price / night
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Luxury Waterfront Stay @ The Galleon, Mins from Downtown
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
Apartment
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Dryer, Extra Bed, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
New to Booking
$675
Average price / night
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Trumans Hideaway by AvantStay Great Location w Patio Outdoor Dining BBQ Shared Pool Week Long Stays
Trumans Hideaway by AvantStay Great Location w Patio Outdoor Dining BBQ Shared Pool Week Long Stays
House
Key West, FL, USA
0.9k from Sunset Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$557
Average price / night
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Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 20-27, 2026
Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 20-27, 2026
Condo
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Arcade, Barbecue, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
New to Booking
$881
Average price / night
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Sundown Refuge by AvantStay Great Location w Patio Outdoor Dining BBQ Shared Pool Week Long Stays
Sundown Refuge by AvantStay Great Location w Patio Outdoor Dining BBQ Shared Pool Week Long Stays
House
Key West, FL, USA
0.9k from Sunset Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom5 Guests
New to Booking
$579
Average price / night
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DOWNTOWN KEY WEST 2BED OCEANFRONT!
DOWNTOWN KEY WEST 2BED OCEANFRONT!
Condo
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Balcony, Dryer, Internet, Laundry, No Smoking, Pool, Washer

2 Bedrooms6 Guests
8.0

Good

2 reviews

$534
Average price / night
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The Beaming Barracuda by Last Key Realty
The Beaming Barracuda by Last Key Realty
House
Key West, FL, USA
1.0k from Sunset Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$790
Average price / night
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2 Sunset Harbor Resort, Pool, Hot Tub, In Town!
2 Sunset Harbor Resort, Pool, Hot Tub, In Town!
Resort
Key West, FL, 33040, United States
0.9k from Sunset Key center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms2 Guests
New to Booking
$2137
Average price / night
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2 Sunset Harbor Resort Key West, Hot Tub, Pool!
2 Sunset Harbor Resort Key West, Hot Tub, Pool!
Resort
Key West, FL, 33040, United States
0.9k from Sunset Key center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
New to Booking
$2025
Average price / night
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2 Sunset Harbor Resort Key West Florida
2 Sunset Harbor Resort Key West Florida
Resort
Key West, FL, 33040, United States
0.9k from Sunset Key center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms2 Guests
New to Booking
$11248
Average price / night
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Tropical Executive at The Truman Annex in Key West
Tropical Executive at The Truman Annex in Key West
Condo
Key West, FL, 33040, United States
0.9k from Sunset Key center

AC, Dryer, Elevator, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.6

Exceptional

27 reviews

$409
Average price / night
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A Sunset & Harbour View at The Truman Annex in Key West
A Sunset & Harbour View at The Truman Annex in Key West
Condo
Key West, FL, 33040, United States
0.9k from Sunset Key center

AC, Balcony, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.6

Exceptional

27 reviews

$411
Average price / night
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Catch of the Day at The Truman Annex in Key West
Catch of the Day at The Truman Annex in Key West
Condo
Key West, FL, 33040, United States
0.9k from Sunset Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
9.6

Exceptional

29 reviews

$554
Average price / night
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Paradise on the Ocean at The Truman Annex in Key West
Paradise on the Ocean at The Truman Annex in Key West
Condo
Key West, FL, 33040, United States
0.9k from Sunset Key center

AC, Balcony, Dryer, Elevator, Extra Bed, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
8.2

Very Good

25 reviews

$443
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Sunset Key.

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Sunset Key Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in Sunset Key. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Sunset Key vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $387 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Sunset Key offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Sunset Key welcome pets. Currently, 19 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Sunset Key often include additional outdoor features such as Pool, Laundry, and Wellness Facilities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Sunset Key offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.