Vacation Rentals with Pool in Paradise Shores, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Sarasota
  6.  Paradise Shores

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3677 Best Vacation Rentals with Pool in Paradise Shores (Starting from $159)

Southside Village Resort
Southside Village Resort
Apartment
Sarasota, FL, USA
0.7k from Paradise Shores center

Fireplace/Heating, Pet Friendly, Pool, Oceanfront, Guest Services, Ocean View, View

4 Bedrooms2 Guests
New to Booking
$175
Average price / night
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Welcome to Off Tropic!
Welcome to Off Tropic!
House
Sarasota, FL, 34239, United States
0.5k from Paradise Shores center

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

3 Bedrooms6 Guests
9.4

Superb

6 reviews

$363
Average price / night
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Coastal Luxe, SaltPool Spa, 5miles to Siesta
Coastal Luxe, SaltPool Spa, 5miles to Siesta
House
Sarasota, FL, USA
1.1k from Paradise Shores center

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

5 Bedrooms18 Guests
9.5

Superb

2 reviews

$989
Average price / night
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Private paradise in exclusive neighborhood
Private paradise in exclusive neighborhood
House
Sarasota, FL, 34239, United States
0.5k from Paradise Shores center

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

3 Bedrooms6 Guests
New to Booking
$568
Average price / night
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Heated Saltwater Pool, Breathtaking outdoor terraces, beautiful landscaping- Villa Serene Escape
Heated Saltwater Pool, Breathtaking outdoor terraces, beautiful landscaping- Villa Serene Escape
House
Paradise Shores, Sarasota, Florida, USA
1.1k from Paradise Shores center

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

6 Bedrooms12 Guests
New to Booking
$456
Average price / night
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Aria 1-bed apartment in Southside village, Sarasota with new pool, WiFi
Aria 1-bed apartment in Southside village, Sarasota with new pool, WiFi
Apartment
Sarasota, FL, 34239, United States
0.6k from Paradise Shores center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Patio, Pool

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$268
Average price / night
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Casamigos - 1805
Casamigos - 1805
House
Sarasota, FL, USA
1.2k from Paradise Shores center

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

4 Bedrooms10 Guests
New to Booking
$1146
Average price / night
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Entire private house
Entire private house
House
Sarasota, FL, 34239, United States
0.7k from Paradise Shores center

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

5 Bedrooms10 Guests
10.0

Exceptional

48 reviews

$545
Average price / night
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Ventana Rosa - 1905
Ventana Rosa - 1905
House
Sarasota, FL, USA
1.3k from Paradise Shores center

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

3 Bedrooms10 Guests
New to Booking
$534
Average price / night
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Sarasota Renovated Waterfront Home with Dock Wide Open Bay Views Heated Pool
Sarasota Renovated Waterfront Home with Dock Wide Open Bay Views Heated Pool
House
Sarasota, FL, 34239, United States
0.7k from Paradise Shores center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$1119
Average price / night
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Organic Fun
Organic Fun
House
Sarasota, FL, USA
1.3k from Paradise Shores center

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

4 Bedrooms8 Guests
5.0

Review score

1 reviews

$433
Average price / night
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Relax at the Blue Buttercup in Sarasota's sweet SouthSide village!
Relax at the Blue Buttercup in Sarasota's sweet SouthSide village!
Apartment
Sarasota, FL, 34239, United States
0.7k from Paradise Shores center

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

1 Bedroom2 Guests
10.0

Exceptional

5 reviews

$176
Average price / night
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Sunny Oasis in Sarasota Florida
Sunny Oasis in Sarasota Florida
House
Sarasota, FL, USA
1.4k from Paradise Shores center

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

1 Bedroom6 Guests
New to Booking
$445
Average price / night
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Southside Bungalow with Pool, Spa & Putting Green
Southside Bungalow with Pool, Spa & Putting Green
House
Sarasota, FL, 34239, United States
0.8k from Paradise Shores center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$534
Average price / night
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PRIVATE POOL OASIS BY SIESTA KEY WITH YOGA RETREAT
PRIVATE POOL OASIS BY SIESTA KEY WITH YOGA RETREAT
Villa
Sarasota, FL, USA
1.4k from Paradise Shores center

Internet, Air Conditioner, Pool, Parking, Kitchen, Child Friendly

2 Bedrooms4 Guests
New to Booking
$536
Average price / night
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Tropical Beach/Town Studio Prime Mainland Location
Tropical Beach/Town Studio Prime Mainland Location
Apartment
Sarasota, FL, 34239, United States
0.9k from Paradise Shores center

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

10.0

Exceptional

35 reviews

$202
Average price / night
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Paradise Palace
Paradise Palace
House
Sarasota, FL, USA
1.7k from Paradise Shores center

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

4 Bedrooms11 Guests
New to Booking
$530
Average price / night
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Arlington Park Area! Heated Pool 3 bedroom/ 2 bath
Arlington Park Area! Heated Pool 3 bedroom/ 2 bath
House
Sarasota, FL, 34239, United States
0.9k from Paradise Shores center

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

3 Bedrooms6 Guests
9.2

Superb

32 reviews

$295
Average price / night
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Pool - Near Beach - Outdoor Games for Family - Close to DT
Pool - Near Beach - Outdoor Games for Family - Close to DT
House
Sarasota, FL, USA
1.7k from Paradise Shores center

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

4 Bedrooms10 Guests
New to Booking
$517
Average price / night
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Amazing Location West of the Trail
Amazing Location West of the Trail
House
Sarasota, FL, 34239, United States
0.9k from Paradise Shores center

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

2 Bedrooms4 Guests
9.6

Exceptional

20 reviews

$276
Average price / night
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The Shaded Sanctuary: Enjoy this beautiful home surrounded by some of Florida's
The Shaded Sanctuary: Enjoy this beautiful home surrounded by some of Florida's
House
Sarasota, FL, 34239, United States
1.0k from Paradise Shores center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$469
Average price / night
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Newly renovated classic villa in exclusive neighborhood.
Newly renovated classic villa in exclusive neighborhood.
House
Sarasota, FL, 34239, United States
1.0k from Paradise Shores center

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

4 Bedrooms8 Guests
9.8

Exceptional

28 reviews

$614
Average price / night
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Coastal Beach Cabana, Siesta Key beach access, best neighborhood in Sarasota!
Coastal Beach Cabana, Siesta Key beach access, best neighborhood in Sarasota!
House
Sarasota, FL, 34239, United States
1.0k from Paradise Shores center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$455
Average price / night
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Tropical Oasis with Private Pool & Spa, minutes from Siesta Key Beach!
Tropical Oasis with Private Pool & Spa, minutes from Siesta Key Beach!
House
Sarasota, FL, 34239, United States
1.1k from Paradise Shores center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$769
Average price / night
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Hidden Oasis Newly Updated Beautiful Condo & Private Courtyard to Wine & Dine!
Hidden Oasis Newly Updated Beautiful Condo & Private Courtyard to Wine & Dine!
Condo
Sarasota, FL, 34239, United States
1.1k from Paradise Shores center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$159
Average price / night
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Coastal Luxe, Spacious 5bedroom house 5miles to Siesta with saltwater pool, WiFi
Coastal Luxe, Spacious 5bedroom house 5miles to Siesta with saltwater pool, WiFi
House
Sarasota, FL, 34239, United States
1.1k from Paradise Shores center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms16 Guests
10.0

Exceptional

8 reviews

$1026
Average price / night
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Near Siesta Key 5BR • Pool, Spa, Outdoor Kitchen
Near Siesta Key 5BR • Pool, Spa, Outdoor Kitchen
House
Sarasota, FL, 34239, United States
1.1k from Paradise Shores center

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

5 Bedrooms8 Guests
New to Booking
$1113
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 Paradise Shores.

Stay Near Paradise Shores's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Paradise Shores Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 3677 verified vacation rentals with a pool in Paradise Shores. 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 Paradise Shores vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $159 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Paradise Shores 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 Paradise Shores welcome pets. Currently, 47 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 Paradise Shores often include additional outdoor features such as Pool, Fireplace/Heating, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Paradise Shores 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.