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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Sarasota
  6.  Siesta Key Beach

Refine your search

Price per night

Amenity Filter

Rating

3554 Best Vacation Rentals with Pool in Siesta Key Beach (Starting from $142)

Beachfront Siesta Key Condo with Pool Access!
Beachfront Siesta Key Condo with Pool Access!
Apartment
Siesta Key, FL, USA
0.3k from Siesta Key Beach center

Apartments, Accommodations, Parking, Spa, Lodgings, Beach, Places to stay, Self-catering, Condos

2 Bedrooms8 Guests
7.0

Good

17 reviews

$216
Average price / night
Check Availability
Condo# 411 Siesta Key Beach Sunsets
Condo# 411 Siesta Key Beach Sunsets
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Internet

2 Bedrooms6 Guests
10.0

Exceptional

46 reviews

$278
Average price / night
Check Availability
Beach Way Getaway
Beach Way Getaway
Apartment
Siesta Key, FL, USA
0.4k from Siesta Key Beach center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
8.0

Good

1 reviews

$306
Average price / night
Check Availability
Condo# 403 Siesta Key- Gulf View
Condo# 403 Siesta Key- Gulf View
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$273
Average price / night
Check Availability
Admirals Watch - 673
Admirals Watch - 673
House
Siesta Key, FL, USA
0.4k from Siesta Key Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

1 Bedroom8 Guests
9.2

Superb

5 reviews

$1344
Average price / night
Check Availability
Condo# 419 Directly across from Siesta Beach - beach, gulf and pool views
Condo# 419 Directly across from Siesta Beach - beach, gulf and pool views
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Internet

2 Bedrooms6 Guests
9.4

Superb

3 reviews

$288
Average price / night
Check Availability
Villa Vista Mare - 675
Villa Vista Mare - 675
House
Siesta Key, FL, USA
0.4k from Siesta Key Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

3 Bedrooms8 Guests
9.8

Exceptional

7 reviews

$1849
Average price / night
Check Availability
Overlooking Siesta Beach Penthouse #408
Overlooking Siesta Beach Penthouse #408
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Living Area

2 Bedrooms6 Guests
New to Booking
$300
Average price / night
Check Availability
Silver Shore - 657B
Silver Shore - 657B
House
Siesta Key, FL, USA
0.4k from Siesta Key Beach center

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

3 Bedrooms12 Guests
New to Booking
$1148
Average price / night
Check Availability
Siesta Key - steps to the beach & pool#108
Siesta Key - steps to the beach & pool#108
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Living Area

2 Bedrooms4 Guests
New to Booking
$279
Average price / night
Check Availability
Crystal Sands - 657A
Crystal Sands - 657A
House
Siesta Key, FL, USA
0.4k from Siesta Key Beach center

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

3 Bedrooms10 Guests
7.0

Good

3 reviews

$912
Average price / night
Check Availability
Extraordinary Beach view of Siesta Key Beach! Condo# 311 - Fully Renovated!
Extraordinary Beach view of Siesta Key Beach! Condo# 311 - Fully Renovated!
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
8.0

Good

4 reviews

$269
Average price / night
Check Availability
Sweet Beach Retreat
Sweet Beach Retreat
Apartment
FL, USA
0.4k from Siesta Key Beach center

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

2 Bedrooms6 Guests
New to Booking
$142
Average price / night
Check Availability
Condo# 404 Beautiful Gulf View on Siesta Key
Condo# 404 Beautiful Gulf View on Siesta Key
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.6

Exceptional

60 reviews

$278
Average price / night
Check Availability
Ocean-Views, Pool, Private Elevator, Covered Patio & Fire-Table, 150 steps to Beach!
Ocean-Views, Pool, Private Elevator, Covered Patio & Fire-Table, 150 steps to Beach!
House
Siesta Key, FL, USA
0.4k from Siesta Key Beach center

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

3 Bedrooms10 Guests
New to Booking
$1325
Average price / night
Check Availability
Condo#407 2 Bed/2 bath Condo Steps to Siesta Key Beach!
Condo#407 2 Bed/2 bath Condo Steps to Siesta Key Beach!
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$290
Average price / night
Check Availability
Beachside Haven - 650C
Beachside Haven - 650C
House
Siesta Key, FL, USA
0.4k from Siesta Key Beach center

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

3 Bedrooms8 Guests
New to Booking
$733
Average price / night
Check Availability
Condo# 416 2 Bed/1 bath Condo Steps to Siesta Key Beach!
Condo# 416 2 Bed/1 bath Condo Steps to Siesta Key Beach!
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.2

Superb

21 reviews

$292
Average price / night
Check Availability
Island Escape - 638
Island Escape - 638
House
Siesta Key, FL, USA
0.5k from Siesta Key Beach center

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

4 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$2136
Average price / night
Check Availability
Condo# 409  Steps from Siesta Key Beach Condo
Condo# 409 Steps from Siesta Key Beach Condo
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.4

Superb

24 reviews

$273
Average price / night
Check Availability
Condo#401 Overlooks Siesta Key Beach Entrance
Condo#401 Overlooks Siesta Key Beach Entrance
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

18 reviews

$273
Average price / night
Check Availability
Unit 103- Paradise Awaits
Unit 103- Paradise Awaits
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

30 reviews

$292
Average price / night
Check Availability
Condo# 219 Siesta key Paradise unit 219
Condo# 219 Siesta key Paradise unit 219
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.4

Superb

14 reviews

$278
Average price / night
Check Availability
Condo#115  2 Bed/1  bath Condo Steps to Siesta Key Beach!
Condo#115 2 Bed/1 bath Condo Steps to Siesta Key Beach!
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

16 reviews

$291
Average price / night
Check Availability
Condo#215 Siesta Key Condominium
Condo#215 Siesta Key Condominium
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
8.8

Fabulous

5 reviews

$278
Average price / night
Check Availability
Condo# 318 2 Bed/1 bath Condo Steps to Siesta Key Beach!
Condo# 318 2 Bed/1 bath Condo Steps to Siesta Key Beach!
Condo
Sarasota, FL, 34242, United States
0.2k from Siesta Key Beach center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Internet

2 Bedrooms6 Guests
3.0

Review score

2 reviews

$278
Average price / night
Check Availability
Vacation Ready 2 Bed 2 bath Siesta Key Beach with Gulf Views Steps to Beach
Vacation Ready 2 Bed 2 bath Siesta Key Beach with Gulf Views Steps to Beach
Condo
Siesta Key, FL, 34242, United States
0.3k from Siesta Key Beach center

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

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$382
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 Siesta Key Beach.

Where to stay in Siesta Key Beach? Best neighborhoods & areas

Siesta Key Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 3554 verified vacation rentals with a pool in Siesta Key Beach. 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 Siesta Key Beach vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $142 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Siesta Key Beach 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 Siesta Key Beach welcome pets. Currently, 10 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 Siesta Key Beach often include additional outdoor features such as Pool, View, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Siesta Key Beach 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.