Holiday rentals near Pioneer Park
We found 6,816 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:8 Aug - 15 Aug
Image gallery for Family friendly 4 bed 2 bath home in a peaceful neighborhood 15min to Siesta Key
1010 out of 10 rating
Exceptional
(31 reviews)
Family friendly 4 bed 2 bath home in a peaceful neighborhood 15min to Siesta Key
Sarasota, FL
7% off
Price is NZ$4,840
NZ$4,840
NZ$691 per night
includes taxes & fees
Image gallery for Siesta Key FamilyGetaway!!
1010 out of 10 rating
Exceptional
(78 reviews)
Siesta Key FamilyGetaway!!
Siesta Key, FL
8% off
Price is NZ$6,264
NZ$6,264
NZ$895 per night
includes taxes & fees
Image gallery for ALL-NEW Waterfront Room, Heated Pool, Tiki Bar/Grill
9.89.8 out of 10 rating
Exceptional
(13 reviews)
ALL-NEW Waterfront Room, Heated Pool, Tiki Bar/Grill
Sarasota, FL
5% off
Price is NZ$2,164
NZ$2,164
NZ$309 per night
includes taxes & fees
Image gallery for Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
1010 out of 10 rating
Exceptional
(43 reviews)
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Bradenton, FL
7% off
Price is NZ$5,799
NZ$5,799
NZ$828 per night
includes taxes & fees
Image gallery for "Siesta Breeze Place", Entire Home minutes to Siesta Key Beach
1010 out of 10 rating
Exceptional
(38 reviews)
"Siesta Breeze Place", Entire Home minutes to Siesta Key Beach
Sarasota, FL
11% off
Price is NZ$3,180
NZ$3,180
NZ$454 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 NZ$13,397
NZ$13,397
NZ$1,914 per night
includes taxes & fees
Image gallery for 2 Minute Walk to Siesta Beach -really!! Great value, great location !!!
9.89.8 out of 10 rating
Exceptional
(56 reviews)
2 Minute Walk to Siesta Beach -really!! Great value, great location !!!
Siesta Key, FL
8% off
Price is NZ$3,833
NZ$3,833
NZ$548 per night
includes taxes & fees
Image gallery for Sandy Feet Retreat | Private Pool, Pergola + Ping Pong!
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Sandy Feet Retreat | Private Pool, Pergola + Ping Pong!
Sarasota, FL
7% off
Price is NZ$5,086
NZ$5,086
NZ$727 per night
includes taxes & fees
Image gallery for Spacious + Vibrant 5-bed 3-bath Private House with Pool in Sarasota/Bradenton
9.29.2 out of 10 rating
Wonderful
(18 reviews)
Spacious + Vibrant 5-bed 3-bath Private House with Pool in Sarasota/Bradenton
Bradenton, FL
8% off
Price is NZ$4,514
NZ$4,514
NZ$645 per night
includes taxes & fees
Image gallery for Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
Siesta Key, FL
6% off
Price is NZ$4,628
NZ$4,628
NZ$661 per night
includes taxes & fees
Image gallery for The Bray Escape. 4.7 Miles to Siesta Key
1010 out of 10 rating
Exceptional
(7 reviews)
The Bray Escape. 4.7 Miles to Siesta Key
Sarasota, FL
7% off
Price is NZ$4,182
NZ$4,182
NZ$597 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 NZ$3,603
NZ$3,603
NZ$515 per night
includes taxes & fees
Image gallery for Florida country club home, short drive to beaches, theme parks & golf
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Florida country club home, short drive to beaches, theme parks & golf
Bradenton, FL
7% off
Price is NZ$4,524
NZ$4,524
NZ$646 per night
includes taxes & fees
Image gallery for Siesta Key Beach HideAway
9.49.4 out of 10 rating
Exceptional
(52 reviews)
Siesta Key Beach HideAway
Siesta Key, FL
8% off
Price is NZ$5,815
NZ$5,815
NZ$831 per night
includes taxes & fees
Image gallery for A Whale of a Good Time!
1010 out of 10 rating
Exceptional
(30 reviews)
A Whale of a Good Time!
Sarasota, FL
8% off
Price is NZ$4,221
NZ$4,221
NZ$603 per night
includes taxes & fees
Image gallery for New listing discount! Beautiful house close to Anna Maria Island and Siesta Key.
9.69.6 out of 10 rating
Exceptional
(12 reviews)
New listing discount! Beautiful house close to Anna Maria Island and Siesta Key.
Bradenton, FL
6% off
Price is NZ$4,675
NZ$4,675
NZ$668 per night
includes taxes & fees
Image gallery for Bayshore Gardens remodel with hot tub + fire pit + walk to park and marina
1010 out of 10 rating
Exceptional
(12 reviews)
Bayshore Gardens remodel with hot tub + fire pit + walk to park and marina
Bradenton, FL
7% off
Price is NZ$3,067
NZ$3,067
NZ$438 per night
includes taxes & fees
Image gallery for Daily sunset & Beach view Enjoy paradise!
9.69.6 out of 10 rating
Exceptional
(70 reviews)
Daily sunset & Beach view Enjoy paradise!
Siesta Key, FL
12% off
Price is NZ$4,338
NZ$4,338
NZ$620 per night
includes taxes & fees
Image gallery for Contemporary, Downtown location, Pool, Spa & Sauna, very close to Beaches
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Contemporary, Downtown location, Pool, Spa & Sauna, very close to Beaches
Sarasota, FL
8% off
Price is NZ$8,497
NZ$8,497
NZ$1,214 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
(26 reviews)
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Bradenton, FL
7% off
Price is NZ$3,290
NZ$3,290
NZ$470 per night
includes taxes & fees
Image gallery for Steps to Siesta Key white sandy beach!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Steps to Siesta Key white sandy beach!
Siesta Key, FL
8% off
Price is NZ$3,909
NZ$3,909
NZ$558 per night
includes taxes & fees
Image gallery for Pool home in Sarasota, Florida. Short drive to Siesta Key beach
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Pool home in Sarasota, Florida. Short drive to Siesta Key beach
Sarasota, FL
7% off
Price is NZ$3,042
NZ$3,042
NZ$435 per night
includes taxes & fees
Image gallery for Modern, newly remodeled with private heated pool.
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Modern, newly remodeled with private heated pool.
Sarasota, FL
8% off
Price is NZ$5,603
NZ$5,603
NZ$800 per night
includes taxes & fees
Image gallery for Freshly remodeled, wonderfully located home in North Sarasota.
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Freshly remodeled, wonderfully located home in North Sarasota.
Sarasota, FL
7% off
Price is NZ$2,908
NZ$2,908
NZ$415 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Pioneer Park
Vacation Home w/ Ocean View, Resort Style Pool W/Slide Sleeps 16
Sleeps 16 · 6 bedrooms · 7 bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
NEW listing: Heated Pool+Pickleball+MiniGolf+TheaterArcade+3 KingBeds
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
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
138 reviews(138 reviews)
Hibiscus Suites - Gateway to Siesta Key
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
2,123 reviews(2,123 reviews)
THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW
Sleeps 4 · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
APR MAY JUNE DISCOUNT! AMI White Sand Beaches/IMG ACADEMY/Pickle Ball/GOLF/FUN!
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
21 reviews(21 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