Vacation Rentals with Pool in Bay Island, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Sarasota
  6.  Bay Island

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3639 Best Vacation Rentals with Pool in Bay Island (Starting from $229)

Family friendly with large pool
Family friendly with large pool
House
Sarasota, FL, USA
0.3k from Bay Island center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1078
Average price / night
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Another Day in Paradise!
Another Day in Paradise!
House
Sarasota, FL, 34242, United States
0.1k from Bay Island center

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

2 Bedrooms5 Guests
10.0

Exceptional

51 reviews

$474
Average price / night
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Casa Leone - 3446
Casa Leone - 3446
House
Siesta Key, FL, USA
0.3k from Bay Island center

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

4 Bedrooms10 Guests
New to Booking
$847
Average price / night
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The Seagrape Villa -Family Friendly- Luxury Accommodation in Paradise
The Seagrape Villa -Family Friendly- Luxury Accommodation in Paradise
House
Sarasota, FL, 34242, United States
0.1k from Bay Island center

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

5 Bedrooms10 Guests
10.0

Exceptional

52 reviews

$676
Average price / night
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Siesta Dolce - 3750
Siesta Dolce - 3750
House
Siesta Key, FL, USA
0.5k from Bay Island center

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

4 Bedrooms6 Guests
New to Booking
$709
Average price / night
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Sunny Siesta Key Retreat w/ Private Heated Pool | 2BR | Dog-Friendly
Sunny Siesta Key Retreat w/ Private Heated Pool | 2BR | Dog-Friendly
House
Siesta Key, FL, 34242, United States
0.2k from Bay Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
New to Booking
$229
Average price / night
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Sunset West - 3360
Sunset West - 3360
House
Siesta Key, FL, USA
0.5k from Bay Island center

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

4 Bedrooms10 Guests
New to Booking
$1121
Average price / night
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Escape to The Big Dipper: Siesta Key Canal Front Home with Pool and Private Dock
Escape to The Big Dipper: Siesta Key Canal Front Home with Pool and Private Dock
House
Siesta Key, FL, 34242, United States
0.3k from Bay Island center

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

4 Bedrooms10 Guests
New to Booking
$1146
Average price / night
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Casa Playa
Casa Playa
House
Bailey Hall, FL, USA
0.5k from Bay Island center

Sports/Activities, Pool, Security/Safety, Fireplace/Heating, Internet, Parking, Child Friendly

1 Bedroom10 Guests
New to Booking
$841
Average price / night
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Salty Sailfish | Private Pool + Hot Tub + Siesta Key
Salty Sailfish | Private Pool + Hot Tub + Siesta Key
House
Sarasota, FL, 34242, United States
0.3k from Bay Island center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$1116
Average price / night
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Shell Beach Home 209
Shell Beach Home 209
House
Sarasota, FL, USA
0.5k from Bay Island center

Accommodations, Pools, Villas, Vacation homes, Cottages, 4-star, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$741
Average price / night
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Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony
Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony
House
Sarasota, FL, 34242, United States
0.3k from Bay Island center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$452
Average price / night
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Your Personal Resort-7BR, Pool, Tennis, Boating &
Your Personal Resort-7BR, Pool, Tennis, Boating &
House
Sarasota, FL, USA
0.5k from Bay Island center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

7 Bedrooms15 Guests
New to Booking
$2068
Average price / night
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Casa Leone | Pet Friendly 🐶 on Siesta Key w/ Private Heated Pool, Golf Cart, & Putting Green!
Casa Leone | Pet Friendly 🐶 on Siesta Key w/ Private Heated Pool, Golf Cart, & Putting Green!
House
Siesta Key, FL, 34242, United States
0.3k from Bay Island center

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

4 Bedrooms10 Guests
9.4

Superb

37 reviews

$720
Average price / night
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Brisas Del Mar
Brisas Del Mar
House
Sarasota, FL, USA
0.5k from Bay Island center

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

4 Bedrooms10 Guests
New to Booking
$779
Average price / night
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AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool
AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool
House
Siesta Key, FL, 34242, United States
0.3k from Bay Island center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking

5 Bedrooms10 Guests
10.0

Exceptional

27 reviews

$1917
Average price / night
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Palm Paradise - Pet Friendly Home on Siesta Key w/Large Heated Private Pool & Outdoor Area!
Palm Paradise - Pet Friendly Home on Siesta Key w/Large Heated Private Pool & Outdoor Area!
House
Sarasota, FL, USA
0.6k from Bay Island center

Spa, Security/Safety, Parking, Internet, Sports/Activities, Pool, Guest Services

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$728
Average price / night
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Siesta Key Sports Paradise- bball, vball, tennis, pickleball
Siesta Key Sports Paradise- bball, vball, tennis, pickleball
House
Sarasota, FL, 34242, United States
0.4k from Bay Island center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$859
Average price / night
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Shore Thing - 185
Shore Thing - 185
House
Siesta Key, FL, USA
0.6k from Bay Island center

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

5 Bedrooms11 Guests
New to Booking
$1133
Average price / night
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Spacious Siesta Key Home with Private Heated Pool – Pet Friendly, Near Beaches
Spacious Siesta Key Home with Private Heated Pool – Pet Friendly, Near Beaches
House
Siesta Key, FL, 34242, United States
0.4k from Bay Island center

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

3 Bedrooms9 Guests
9.0

Fabulous

53 reviews

$413
Average price / night
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Shell Beach - The Treehouse 210
Shell Beach - The Treehouse 210
House
Sarasota, FL, USA
0.6k from Bay Island center

Luxury, Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, 4-star, Lodgings

4 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$449
Average price / night
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Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Villa
Sarasota, FL, 34242, United States
0.4k from Bay Island center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

7 Bedrooms14 Guests
10.0

Exceptional

10 reviews

$1963
Average price / night
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Sunset West | Private Pool, Spa, Near Siesta Key Beach & Siesta Key Village
Sunset West | Private Pool, Spa, Near Siesta Key Beach & Siesta Key Village
House
Siesta Key, FL, 34242, United States
0.5k from Bay Island center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$710
Average price / night
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Beachside Private Vacation Home w/ Large Heated Pool
Beachside Private Vacation Home w/ Large Heated Pool
House
Sarasota, FL, 34242, United States
0.5k from Bay Island center

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

3 Bedrooms6 Guests
9.4

Superb

54 reviews

$443
Average price / night
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Holiday Sunshine Savings: Luxurious Waterfront Retreat minutes from beach
Holiday Sunshine Savings: Luxurious Waterfront Retreat minutes from beach
House
Siesta Key, FL, 34242, United States
0.5k from Bay Island center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
10.0

Exceptional

56 reviews

$1218
Average price / night
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Dog-friendly gated spacious Siesta Key Getaway — Pool, Spa, & Mancave.
Dog-friendly gated spacious Siesta Key Getaway — Pool, Spa, & Mancave.
House
Siesta Key, FL, 34242, United States
0.5k from Bay Island center

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

5 Bedrooms10 Guests
9.8

Exceptional

13 reviews

$984
Average price / night
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Stunning Siesta Key,,  .  , Walk to Shell Beach, HEATED POOL - Discounts
Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts
House
Sarasota, FL, 34242, United States
0.5k from Bay Island center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms14 Guests
9.8

Exceptional

128 reviews

$646
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 Bay Island.

Where to stay in Bay Island? Best neighborhoods & areas

Bay Island Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 3639 verified vacation rentals with a pool in Bay Island. 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 Bay Island vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $229 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Bay Island 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 Bay Island welcome pets. Currently, 54 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 Bay Island 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 Bay Island 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.