Holiday rentals near Pioneer Park
We found 6,909 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:14 Nov - 21 Nov
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 AU$5,766
AU$5,766
AU$824 nightly
Includes taxes & fees
Image gallery for Enjoy a new remodeled house minutes away from Anna Maria Island
8.68.6 out of 10 rating
Excellent
(8 reviews)
Enjoy a new remodeled house minutes away from Anna Maria Island
Bradenton, FL
8% off
Price is AU$2,849
AU$2,849
AU$407 nightly
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
(15 reviews)
Royal Palms Oasis | Pickle Ball, Pet-Friendly w/ Private Pool + Putt Putt
Sarasota, FL
7% off
Price is AU$4,019
AU$4,019
AU$574 nightly
Includes taxes & fees
Image gallery for Private Pool & Beach Access, 2-car Garage, Beach toys & Smart TVs
1010 out of 10 rating
Exceptional
(39 reviews)
Private Pool & Beach Access, 2-car Garage, Beach toys & Smart TVs
Siesta Key, FL
8% off
Price is AU$13,606
AU$13,606
AU$1,944 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
6% off
Price is AU$4,615
AU$4,615
AU$659 nightly
Includes taxes & fees
Image gallery for Siesta Key FamilyGetaway!!
1010 out of 10 rating
Exceptional
(83 reviews)
Siesta Key FamilyGetaway!!
Siesta Key, FL
8% off
Price is AU$6,004
AU$6,004
AU$858 nightly
Includes taxes & fees
Image gallery for 2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things
1010 out of 10 rating
Exceptional
(106 reviews)
2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things
Siesta Key, FL
8% off
Price is AU$13,606
AU$13,606
AU$1,944 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 AU$4,805
AU$4,805
AU$686 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
(23 reviews)
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Sarasota, FL
7% off
Price is AU$2,072
AU$2,072
AU$296 nightly
Includes taxes & fees
Image gallery for Sandy Feet Retreat | Private Pool + Ping Pong!
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Sandy Feet Retreat | Private Pool + Ping Pong!
Sarasota, FL
7% off
Price is AU$4,063
AU$4,063
AU$580 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
6% off
Price is AU$5,137
AU$5,137
AU$734 nightly
Includes taxes & fees
Image gallery for Book now, and make memories that will last a lifetime in the heart of Sarasota!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Book now, and make memories that will last a lifetime in the heart of Sarasota!
Sarasota, FL
8% off
Price is AU$2,565
AU$2,565
AU$366 nightly
Includes taxes & fees
Image gallery for Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
1010 out of 10 rating
Exceptional
(17 reviews)
Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
Sarasota, FL
6% off
Price is AU$2,787
AU$2,787
AU$398 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 AU$3,012
AU$3,012
AU$430 nightly
Includes taxes & fees
Image gallery for Oceanfront home w/sunset views of Sarasota Bay
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Oceanfront home w/sunset views of Sarasota Bay
Sarasota, FL
8% off
Price is AU$4,764
AU$4,764
AU$681 nightly
Includes taxes & fees
Image gallery for Fall Into Paradise Your Endless Summer Starts Now
9.69.6 out of 10 rating
Exceptional
(79 reviews)
Fall Into Paradise Your Endless Summer Starts Now
Siesta Key, FL
6% off
Price is AU$5,711
AU$5,711
AU$816 nightly
Includes taxes & fees
Image gallery for Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
1010 out of 10 rating
Exceptional
(66 reviews)
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Sarasota, FL
8% off
Price is AU$1,573
AU$1,573
AU$225 nightly
Includes taxes & fees
Image gallery for Fall Into Paradise 7 Night Stay
9.09.0 out of 10 rating
Wonderful
(43 reviews)
Fall Into Paradise 7 Night Stay
Sarasota, FL
9% off
Price is AU$3,452
AU$3,452
AU$493 nightly
Includes taxes & fees
Image gallery for 3 bedroom Home with Pool Near Downtown.
9.29.2 out of 10 rating
Wonderful
(44 reviews)
3 bedroom Home with Pool Near Downtown.
Sarasota, FL
5% off
Price is AU$2,425
AU$2,425
AU$346 nightly
Includes taxes & fees
Image gallery for New home 3/2 renovation 3 miles to Siesta Key
9.29.2 out of 10 rating
Wonderful
(19 reviews)
New home 3/2 renovation 3 miles to Siesta Key
Sarasota, FL
7% off
Price is AU$1,960
AU$1,960
AU$280 nightly
Includes taxes & fees
Image gallery for BEAUTIFULL VACATION HOUSE
9.49.4 out of 10 rating
Exceptional
(21 reviews)
BEAUTIFULL VACATION HOUSE
Sarasota, FL
7% off
Price is AU$2,220
AU$2,220
AU$317 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 AU$2,711
AU$2,711
AU$387 nightly
Includes taxes & fees
Image gallery for Executive Bayside Retreat/Pool/IMG/Sarasota Bay
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Executive Bayside Retreat/Pool/IMG/Sarasota Bay
Bradenton, FL
8% off
Price is AU$12,930
AU$12,930
AU$1,847 nightly
Includes taxes & fees
Image gallery for Fall Into Paradise Your Endless Summer Starts Now
9.49.4 out of 10 rating
Exceptional
(50 reviews)
Fall Into Paradise Your Endless Summer Starts Now
Siesta Key, FL
6% off
Price is AU$4,728
AU$4,728
AU$675 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
2,159 reviews(2,159 reviews)
Swivel On Anchor
Sleeps 4 · 2 bedrooms
2.02.0 out of 10
1 review(1 review)
AUG SEPT OCT 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)
THE BEACH #107 Summer special 210 nite+fees Beachfront Full View
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
148 reviews(148 reviews)
Siesta Key Island Rentals
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
44 reviews(44 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