Holiday rentals near Pioneer Park
We found 6,898 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:3 Oct - 10 Oct
Image gallery for Private Oasis in Sarasota Florida
1010 out of 10 rating
Exceptional
(35 reviews)
Private Oasis in Sarasota Florida
Sarasota, FL
11% off
Price is AU$4,932
AU$4,932
AU$705 per night
includes taxes & fees
Image gallery for Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Bradenton, FL
7% off
Price is AU$3,069
AU$3,069
AU$438 per night
includes taxes & fees
Image gallery for Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
1010 out of 10 rating
Exceptional
(18 reviews)
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Bradenton, FL
7% off
Price is AU$1,997
AU$1,997
AU$285 per night
includes taxes & fees
Image gallery for Tiny Home sleeps 6 near beautiful beaches and entertainment
1010 out of 10 rating
Exceptional
(10 reviews)
Tiny Home sleeps 6 near beautiful beaches and entertainment
Bradenton, FL
7% off
Price is AU$1,904
AU$1,904
AU$272 per night
includes taxes & fees
Image gallery for Charming Longboat Key Bungalow with private beach 5 min walk away
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Charming Longboat Key Bungalow with private beach 5 min walk away
Longboat Key, FL
7% off
Price is AU$2,247
AU$2,247
AU$321 per night
includes taxes & fees
Image gallery for Beautiful Family-sized Home in Sunny Sarasota, Florida with large backyard!
8.68.6 out of 10 rating
Excellent
(7 reviews)
Beautiful Family-sized Home in Sunny Sarasota, Florida with large backyard!
Sarasota, FL
11% off
Price is AU$1,737
AU$1,737
AU$248 per night
includes taxes & fees
Image gallery for Spacious pool home minutes from Siesta Key and downtown
1010 out of 10 rating
Exceptional
(5 reviews)
Spacious pool home minutes from Siesta Key and downtown
Sarasota, FL
10% off
Price is AU$2,176
AU$2,176
AU$311 per night
includes taxes & fees
Image gallery for Pool House - Heated Private Pool, Central Location near IMG, Sports courts!
8.88.8 out of 10 rating
Excellent
(19 reviews)
Pool House - Heated Private Pool, Central Location near IMG, Sports courts!
Bradenton, FL
7% off
Price is AU$4,755
AU$4,755
AU$679 per night
includes taxes & fees
Image gallery for Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
1010 out of 10 rating
Exceptional
(6 reviews)
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Siesta Key, FL
8% off
Price is AU$21,547
AU$21,547
AU$3,078 per night
includes taxes & fees
Image gallery for Cozy Coastal Getaway - 2 min Walk to Beach & Village, Shops & Restaurants
1010 out of 10 rating
Exceptional
(12 reviews)
Cozy Coastal Getaway - 2 min Walk to Beach & Village, Shops & Restaurants
Siesta Key, FL
12% off
Price is AU$3,470
AU$3,470
AU$496 per night
includes taxes & fees
Image gallery for A+ location #1 Beach Siesta Key w heated pool, arcade, & small dog friendly
8.68.6 out of 10 rating
Excellent
(7 reviews)
A+ location #1 Beach Siesta Key w heated pool, arcade, & small dog friendly
Siesta Key, FL
7% off
Price is AU$2,791
AU$2,791
AU$399 per night
includes taxes & fees
Image gallery for Royal Palms Oasis | Pickle Ball, Pet-Friendly w/ Private Pool + Putt Putt
9.29.2 out of 10 rating
Wonderful
(13 reviews)
Royal Palms Oasis | Pickle Ball, Pet-Friendly w/ Private Pool + Putt Putt
Sarasota, FL
7% off
Price is AU$3,571
AU$3,571
AU$510 per night
includes taxes & fees
Image gallery for Private Siesta Key Home with Great Location walk to Village and Beach!
1010 out of 10 rating
Exceptional
(20 reviews)
Private Siesta Key Home with Great Location walk to Village and Beach!
Siesta Key, FL
8% off
Price is AU$11,938
AU$11,938
AU$1,705 per night
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
7% off
Price is AU$2,425
AU$2,425
AU$346 per night
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 AU$1,988
AU$1,988
AU$284 per night
includes taxes & fees
Image gallery for Spacious and Bright Townhome on beautiful Longboat Key
1010 out of 10 rating
Exceptional
(17 reviews)
Spacious and Bright Townhome on beautiful Longboat Key
Longboat Key, FL
8% off
Price is AU$2,935
AU$2,935
AU$419 per night
includes taxes & fees
Image gallery for Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate
9.89.8 out of 10 rating
Exceptional
(77 reviews)
Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate
Sarasota, FL
7% off
Price is AU$3,265
AU$3,265
AU$466 per night
includes taxes & fees
Image gallery for Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
9.69.6 out of 10 rating
Exceptional
(104 reviews)
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Siesta Key, FL
15% off
Price is AU$2,885
AU$2,885
AU$412 per night
includes taxes & fees
Image gallery for Tiki Gardens House, Sarasota, Florida, with dipping Pool, Tiki bar +++
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Tiki Gardens House, Sarasota, Florida, with dipping Pool, Tiki bar +++
Sarasota, FL
7% off
Price is AU$3,057
AU$3,057
AU$437 per night
includes taxes & fees
Image gallery for Florida country club home, short drive to beaches, theme parks & golf
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Florida country club home, short drive to beaches, theme parks & golf
Bradenton, FL
8% off
Price is AU$5,280
AU$5,280
AU$754 per night
includes taxes & fees
Image gallery for Get To the Beach! Only 5 miles to Siesta Key Beach!
1010 out of 10 rating
Exceptional
(48 reviews)
Get To the Beach! Only 5 miles to Siesta Key Beach!
Sarasota, FL
5% off
Price is AU$1,714
AU$1,714
AU$245 per night
includes taxes & fees
Image gallery for Charming Beach Cottage
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Charming Beach Cottage
Sarasota, FL
14% off
Price is AU$1,882
AU$1,882
AU$269 per night
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
(29 reviews)
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Sarasota, FL
7% off
Price is AU$3,299
AU$3,299
AU$471 per night
includes taxes & fees
Image gallery for Renovated Modern Spacious Ranch with Pool near Siesta Key Beach and Downtown SRQ
1010 out of 10 rating
Exceptional
(11 reviews)
Renovated Modern Spacious Ranch with Pool near Siesta Key Beach and Downtown SRQ
Sarasota, FL
6% off
Price is AU$4,496
AU$4,496
AU$642 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Pioneer Park
Swivel On Anchor
Sleeps 4 · 2 bedrooms
2.02.0 out of 10
1 review(1 review)
THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW
Sleeps 4 · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
JULY AUG SEPT DISCOUNT! AMI White Sand Beaches/IMG ACADEMY/Pickle Ball/GOLF/FUN!
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Beach Cottage with a Private Hot Tub
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
61 reviews(61 reviews)
Hibiscus Suites - Gateway to Siesta Key
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
2,141 reviews(2,141 reviews)
Last Hoorah
Sleeps 4 · 1 bedroom
2.02.0 out of 10
3 reviews(3 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