Holiday rentals near Pioneer Park
We found 6,920 holiday rentals — enter your dates for availability
Select the perfect holiday home within easy reach of Pioneer Park. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as a garden and pool. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Pioneer Park
Showing deals for:21 Nov - 28 Nov
Image gallery for Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Bradenton, FL
8% off
Price is NZ$5,061
NZ$5,061
NZ$723 nightly
Includes taxes & fees
Image gallery for Modern near Siesta Beach
9.89.8 out of 10 rating
Exceptional
(44 reviews)
Modern near Siesta Beach
Sarasota, FL
8% off
Price is NZ$6,438
NZ$6,438
NZ$920 nightly
Includes taxes & fees
Image gallery for Stunning Fully Remodeled House with Heated Pool! 30%OFF
9.29.2 out of 10 rating
Wonderful
(51 reviews)
Stunning Fully Remodeled House with Heated Pool! 30%OFF
Sarasota, FL
8% off
Price is NZ$5,603
NZ$5,603
NZ$800 nightly
Includes taxes & fees
Image gallery for Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
1010 out of 10 rating
Exceptional
(41 reviews)
Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
Sarasota, FL
8% off
Price is NZ$5,626
NZ$5,626
NZ$804 nightly
Includes taxes & fees
Image gallery for Fall Into Paradise Your Endless Summer Starts Now
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Fall Into Paradise Your Endless Summer Starts Now
Siesta Key, FL
8% off
Price is NZ$5,255
NZ$5,255
NZ$751 nightly
Includes taxes & fees
Image gallery for Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Sarasota, FL
7% off
Price is NZ$1,883
NZ$1,883
NZ$269 nightly
Includes taxes & fees
Image gallery for Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
1010 out of 10 rating
Exceptional
(32 reviews)
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Sarasota, FL
7% off
Price is NZ$4,988
NZ$4,988
NZ$713 nightly
Includes taxes & fees
Image gallery for Fall Into Paradise Your Endless Summer Starts Now
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Fall Into Paradise Your Endless Summer Starts Now
Siesta Key, FL
8% off
Price is NZ$6,326
NZ$6,326
NZ$904 nightly
Includes taxes & fees
Image gallery for Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
9.49.4 out of 10 rating
Exceptional
(24 reviews)
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Sarasota, FL
7% off
Price is NZ$2,294
NZ$2,294
NZ$328 nightly
Includes taxes & fees
Image gallery for Tiki Tide Villa | Private POOL + Tiki Hut!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Tiki Tide Villa | Private POOL + Tiki Hut!
Sarasota, FL
7% off
Price is NZ$6,930
NZ$6,930
NZ$990 nightly
Includes taxes & fees
Image gallery for Welcome To Shoreline: 4BR, Heated Pool, 7miles to Gulf Beaches, Sleeps10
1010 out of 10 rating
Exceptional
(12 reviews)
Welcome To Shoreline: 4BR, Heated Pool, 7miles to Gulf Beaches, Sleeps10
Sarasota, FL
7% off
Price is NZ$6,242
NZ$6,242
NZ$892 nightly
Includes taxes & fees
Image gallery for Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Siesta Key, FL
8% off
Price is NZ$6,260
NZ$6,260
NZ$894 nightly
Includes taxes & fees
Image gallery for Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
Sarasota, FL
6% off
Price is NZ$3,760
NZ$3,760
NZ$537 nightly
Includes taxes & fees
Image gallery for Fall Into Paradise 7 Night Stay
9.09.0 out of 10 rating
Wonderful
(44 reviews)
Fall Into Paradise 7 Night Stay
Sarasota, FL
7% off
Price is NZ$3,768
NZ$3,768
NZ$538 nightly
Includes taxes & fees
Image gallery for Sunshine Haven | HUGE Backyard, Private heated Pool + Fire Pit!
1010 out of 10 rating
Exceptional
(12 reviews)
Sunshine Haven | HUGE Backyard, Private heated Pool + Fire Pit!
Sarasota, FL
6% off
Price is NZ$3,562
NZ$3,562
NZ$509 nightly
Includes taxes & fees
Image gallery for Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
9.49.4 out of 10 rating
Exceptional
(135 reviews)
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Siesta Key, FL
8% off
Price is NZ$3,060
NZ$3,060
NZ$437 nightly
Includes taxes & fees
Image gallery for Southside Bungalow with Pool, Spa & Putting Green
1010 out of 10 rating
Exceptional
(9 reviews)
Southside Bungalow with Pool, Spa & Putting Green
Sarasota, FL
8% off
Price is NZ$7,339
NZ$7,339
NZ$1,048 nightly
Includes taxes & fees
Image gallery for Bright & Beachy - Steps to the water! Community pool closure Aug 4-31st
1010 out of 10 rating
Exceptional
(90 reviews)
Bright & Beachy - Steps to the water! Community pool closure Aug 4-31st
Siesta Key, FL
8% off
Price is NZ$4,723
NZ$4,723
NZ$675 nightly
Includes taxes & fees
Image gallery for Fall Into Paradise Your Endless Summer Starts Now
9.69.6 out of 10 rating
Exceptional
(80 reviews)
Fall Into Paradise Your Endless Summer Starts Now
Siesta Key, FL
9% off
Price is NZ$8,112
NZ$8,112
NZ$1,159 nightly
Includes taxes & fees
Image gallery for Hyde Park Villa w/ Saltwater Pool + Fire Place!
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Hyde Park Villa w/ Saltwater Pool + Fire Place!
Sarasota, FL
7% off
Price is NZ$4,627
NZ$4,627
NZ$661 nightly
Includes taxes & fees
Image gallery for Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
1010 out of 10 rating
Exceptional
(67 reviews)
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Sarasota, FL
8% off
Price is NZ$1,783
NZ$1,783
NZ$255 nightly
Includes taxes & fees
Image gallery for Coastal Pool Bungalow - 15 Mins to Famous Beaches
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Coastal Pool Bungalow - 15 Mins to Famous Beaches
Sarasota, FL
12% off
Price is NZ$3,030
NZ$3,030
NZ$433 nightly
Includes taxes & fees
Image gallery for Fall Into Paradise Your Endless Summer Starts Now
9.49.4 out of 10 rating
Exceptional
(72 reviews)
Fall Into Paradise Your Endless Summer Starts Now
Siesta Key, FL
6% off
Price is NZ$5,442
NZ$5,442
NZ$777 nightly
Includes taxes & fees
Image gallery for Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
1010 out of 10 rating
Exceptional
(239 reviews)
Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
Siesta Key, FL
8% off
Price is NZ$4,140
NZ$4,140
NZ$591 nightly
Includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Pioneer Park
Hibiscus Suites - Gateway to Siesta Key
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
2,162 reviews(2,162 reviews)
SEPT OCT NOV DISCOUNTS! AMI White Sand Beaches/IMG ACADEMY/Pickle Ball/GOLF/FUN!
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Swivel On Anchor
Sleeps 4 · 2 bedrooms
2.02.0 out of 10
1 review(1 review)
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
149 reviews(149 reviews)
THE BEACH #107 Summer special 210 nite+fees Beachfront Full View
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
Siesta Key Island Rentals
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value