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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Shark Key

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134 Best Vacation Rentals with Pool in Shark Key (Starting from $281)

Dock and Balcony Serene Big Coppitt Key Escape
Dock and Balcony Serene Big Coppitt Key Escape
House
Key West, FL, USA
1.2k from Shark Key center

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

3 Bedrooms6 Guests
New to Booking
$281
Average price / night
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Beautiful 3 bedroom 2 bath pool house close to Key West
Beautiful 3 bedroom 2 bath pool house close to Key West
House
Big Coppitt Key, FL, 33040, United States
1.0k from Shark Key center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$400
Average price / night
Check Availability
Ritaville - Monthly Rental
Ritaville - Monthly Rental
House
Stock Island, FL, USA
3.5k from Shark Key center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms11 Guests
New to Booking
$641
Average price / night
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Custom Pool home with Dazzling Ocean Views of the crystal clear Florida Keys waters!
Custom Pool home with Dazzling Ocean Views of the crystal clear Florida Keys waters!
House
Big Coppitt Key, FL, 33040, United States
1.0k from Shark Key center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Hot Tub, Internet

3 Bedrooms8 Guests
New to Booking
$608
Average price / night
Check Availability
Parking Pool Dock - Starboard House
Parking Pool Dock - Starboard House
House
Key West, FL, USA
8.8k from Shark Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms20 Guests
New to Booking
$2900
Average price / night
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Blue Gem | Family-Friendly Waterfront  w/Pool, Tiki Bar/Dock (Monthly Stay)
Blue Gem | Family-Friendly Waterfront w/Pool, Tiki Bar/Dock (Monthly Stay)
House
Key West, FL, 33040, United States
1.1k from Shark Key center

AC, Barbecue, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$329
Average price / night
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Parking Pool & Dock - Shellstone House
Parking Pool & Dock - Shellstone House
House
Key West, FL, USA
8.8k from Shark Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$3262
Average price / night
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Fisherman's Paradise on the Water
Fisherman's Paradise on the Water
House
Key West, FL, 33040, United States
1.1k from Shark Key center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$369
Average price / night
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The Fairhaven House at Solaire Lunara Bay
The Fairhaven House at Solaire Lunara Bay
House
Key West, FL, USA
8.8k from Shark Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom16 Guests
New to Booking
$3719
Average price / night
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**INFINITE HORIZONS @ BIG COPPITT** Waterfront Home & Pool + LAST KEY SERVICES…
**INFINITE HORIZONS @ BIG COPPITT** Waterfront Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
1.3k from Shark Key center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$757
Average price / night
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The Joyrise House at Solaire Lunara Bay
The Joyrise House at Solaire Lunara Bay
House
Key West, FL, USA
8.8k from Shark Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$5185
Average price / night
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The Great Escape: 3BR Waterfront Retreat, Heated Pool, Stunning Sunsets & Just Minutes to Key West
The Great Escape: 3BR Waterfront Retreat, Heated Pool, Stunning Sunsets & Just Minutes to Key West
House
Key West, FL, 33040, United States
2.3k from Shark Key center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
New to Booking
$401
Average price / night
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New Waterfront Home - Sunray House
New Waterfront Home - Sunray House
House
Key West, FL, USA
8.9k from Shark Key center

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

8 Bedrooms16 Guests
New to Booking
$3045
Average price / night
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Home in Blue water Key
Home in Blue water Key
House
Key West, FL, 33040, United States
4.7k from Shark Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$562
Average price / night
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Waterfront Luxury Home - Tidelands House
Waterfront Luxury Home - Tidelands House
House
Key West, FL, USA
8.9k from Shark Key center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$3045
Average price / night
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Key West Beach House with heated pool, tiki, and dock.♿︎
Key West Beach House with heated pool, tiki, and dock.♿︎
House
Key West, FL, 33040, United States
5.6k from Shark Key center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms10 Guests
9.6

Exceptional

8 reviews

$646
Average price / night
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New Waterfront Home - Dreamside House
New Waterfront Home - Dreamside House
House
Key West, FL, USA
8.9k from Shark Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$1924
Average price / night
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Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount
Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount
House
Key West, FL, 33040, United States
5.7k from Shark Key center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.4

Superb

15 reviews

$346
Average price / night
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Mastway House -Pool & Dock!
Mastway House -Pool & Dock!
House
Key West, FL, USA
8.9k from Shark Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$2907
Average price / night
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Sunset Bay: Spacious 5BR Getaway, Dockage, Heated Pool, Dog OK, Stunning Views & Minutes to Key West
Sunset Bay: Spacious 5BR Getaway, Dockage, Heated Pool, Dog OK, Stunning Views & Minutes to Key West
House
Saddlebunch Key, FL, 33040, United States
5.8k from Shark Key center

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

5 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$419
Average price / night
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The Crestwood House - Private Heated Pool & Parking
The Crestwood House - Private Heated Pool & Parking
House
Key West, FL, USA
9.0k from Shark Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

6 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$2969
Average price / night
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Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!
Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!
House
Key West, FL, 33040, United States
5.8k from Shark Key center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms8 Guests
New to Booking
$331
Average price / night
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Luxurious Oceanfront 5BR Property with heated Pool & Waterfall
Luxurious Oceanfront 5BR Property with heated Pool & Waterfall
House
Key West, FL, 33040, United States
5.9k from Shark Key center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
10.0

Exceptional

9 reviews

$851
Average price / night
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Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!
Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!
House
Key West, FL, 33040, United States
5.9k from Shark Key center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$703
Average price / night
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Ocean 9 Villa, Amazing Waterfront, 15 mins away from Duval Street!
Ocean 9 Villa, Amazing Waterfront, 15 mins away from Duval Street!
House
Key West, FL, 33040, United States
6.1k from Shark Key center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms12 Guests
New to Booking
$703
Average price / night
Check Availability
The Perfect Catch: Family Fun and Boater's Bliss in the Keys!
The Perfect Catch: Family Fun and Boater's Bliss in the Keys!
House
Lower Florida Keys, FL, 33042, United States
8.4k from Shark Key center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
New to Booking
$684
Average price / night
Check Availability
**OCEANFRONT OASIS @ KEY HAVEN** Private Home & Pool + LAST KEY SERVICES…
**OCEANFRONT OASIS @ KEY HAVEN** Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
8.8k from Shark Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$836
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 Shark Key.

Where to stay in Shark Key? Best neighborhoods & areas

Shark Key Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 134 verified vacation rentals with a pool in Shark 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 Shark Key vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $281 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Shark 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 Shark Key welcome pets. Currently, 73 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 Shark Key often include additional outdoor features such as Pool, Wellness Facilities, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Shark 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.