Holiday rentals near Pioneer Park
We found 6,870 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:19 Sept - 26 Sept
Image gallery for Condo on the beach! Footsteps to water. Spacious unit with a view.
1010 out of 10 rating
Exceptional
(31 reviews)
Condo on the beach! Footsteps to water. Spacious unit with a view.
Siesta Key, FL
8% off
Price is AU$4,129
AU$4,129
AU$590 per night
includes taxes & fees
Image gallery for Newly Remodeled! Pool home near Siesta Beach!
1010 out of 10 rating
Exceptional
(30 reviews)
Newly Remodeled! Pool home near Siesta Beach!
Siesta Key, FL
8% off
Price is AU$5,109
AU$5,109
AU$730 per night
includes taxes & fees
Image gallery for Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
1010 out of 10 rating
Exceptional
(12 reviews)
Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
Siesta Key, FL
6% off
Price is AU$4,208
AU$4,208
AU$601 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$2,255
AU$2,255
AU$322 per night
includes taxes & fees
Image gallery for Siesta Key Vacation Property W/Heated Pool and Beach Access
1010 out of 10 rating
Exceptional
(50 reviews)
Siesta Key Vacation Property W/Heated Pool and Beach Access
Siesta Key, FL
7% off
Price is AU$4,606
AU$4,606
AU$658 per night
includes taxes & fees
Image gallery for Private Pool & Beach Access, 2-car Garage, Beach toys & Smart TVs
1010 out of 10 rating
Exceptional
(37 reviews)
Private Pool & Beach Access, 2-car Garage, Beach toys & Smart TVs
Siesta Key, FL
5% off
Price is AU$12,213
AU$12,213
AU$1,745 per night
includes taxes & fees
Image gallery for 2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things
1010 out of 10 rating
Exceptional
(97 reviews)
2-Car Garage, Private Pool & Beach Access, BBQ grill & Pool/Beach Things
Siesta Key, FL
5% off
Price is AU$12,213
AU$12,213
AU$1,745 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 AU$5,701
AU$5,701
AU$814 per night
includes taxes & fees
Image gallery for Directly on Siesta Key Beach with a short walk to the Village
9.69.6 out of 10 rating
Exceptional
(67 reviews)
Directly on Siesta Key Beach with a short walk to the Village
Siesta Key, FL
7% off
Price is AU$3,158
AU$3,158
AU$451 per night
includes taxes & fees
Image gallery for “MOONMIST” Siesta Key villa with private hot tub in a 'jungle' setting
9.29.2 out of 10 rating
Wonderful
(93 reviews)
“MOONMIST” Siesta Key villa with private hot tub in a 'jungle' setting
Siesta Key, FL
8% off
Price is AU$2,091
AU$2,091
AU$299 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
(45 reviews)
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Bradenton, FL
7% off
Price is AU$4,527
AU$4,527
AU$647 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
(35 reviews)
Florida country club home, short drive to beaches, theme parks & golf
Bradenton, FL
7% off
Price is AU$4,114
AU$4,114
AU$588 per night
includes taxes & fees
Image gallery for 5 minutes to private Siesta Key Beach + 2 heated pools and pickleball courts
1010 out of 10 rating
Exceptional
(10 reviews)
5 minutes to private Siesta Key Beach + 2 heated pools and pickleball courts
Siesta Key, FL
8% off
Price is AU$3,826
AU$3,826
AU$547 per night
includes taxes & fees
Image gallery for Fun-n-Sun Steps to#1 Beach in USA Spacious 2+2Condo,pool,garage Tranquil Setting
9.89.8 out of 10 rating
Exceptional
(150 reviews)
Fun-n-Sun Steps to#1 Beach in USA Spacious 2+2Condo,pool,garage Tranquil Setting
Siesta Key, FL
7% off
Price is AU$2,659
AU$2,659
AU$380 per night
includes taxes & fees
Image gallery for Steps to Siesta Key beach, condo w/view!
9.89.8 out of 10 rating
Exceptional
(83 reviews)
Steps to Siesta Key beach, condo w/view!
Siesta Key, FL
8% off
Price is AU$3,377
AU$3,377
AU$482 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 AU$4,251
AU$4,251
AU$607 per night
includes taxes & fees
Image gallery for The Bray Escape. 4.7 Miles to Siesta Key
1010 out of 10 rating
Exceptional
(9 reviews)
The Bray Escape. 4.7 Miles to Siesta Key
Sarasota, FL
7% off
Price is AU$3,914
AU$3,914
AU$559 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
14% off
Price is AU$2,489
AU$2,489
AU$356 per night
includes taxes & fees
Image gallery for condo/on beach 1st floor/view of ocean from lanai siesta key beach
9.69.6 out of 10 rating
Exceptional
(41 reviews)
condo/on beach 1st floor/view of ocean from lanai siesta key beach
Siesta Key, FL
8% off
Price is AU$3,190
AU$3,190
AU$456 per night
includes taxes & fees
Image gallery for Sandy Feet Retreat | Private Pool, Pergola + Ping Pong!
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Sandy Feet Retreat | Private Pool, Pergola + Ping Pong!
Sarasota, FL
7% off
Price is AU$3,926
AU$3,926
AU$561 per night
includes taxes & fees
Image gallery for A Whale of a Good Time!
1010 out of 10 rating
Exceptional
(31 reviews)
A Whale of a Good Time!
Sarasota, FL
8% off
Price is AU$3,831
AU$3,831
AU$547 per night
includes taxes & fees
Image gallery for 4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
1010 out of 10 rating
Exceptional
(136 reviews)
4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
Siesta Key, FL
7% off
Price is AU$4,301
AU$4,301
AU$614 per night
includes taxes & fees
Image gallery for Sunny Oasis: Bright, Private and Beautiful Retreat! Magnolia Rentals
1010 out of 10 rating
Exceptional
(63 reviews)
Sunny Oasis: Bright, Private and Beautiful Retreat! Magnolia Rentals
Sarasota, FL
7% off
Price is AU$3,704
AU$3,704
AU$529 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 AU$2,642
AU$2,642
AU$377 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Pioneer Park
Showing deals for: 17 Sept - 20 Sept
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
23 reviews(23 reviews)
The current price is AU$1,398
AU$1,398
for 3 nights, 1 home
AU$466 per night
includes taxes & fees
Hibiscus Suites - Gateway to Siesta Key
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
2,134 reviews(2,134 reviews)
The current price is AU$686
AU$686
for 3 nights, 1 room
AU$229 per night
includes taxes & fees
Swivel On Anchor
Sleeps 4 · 2 bedrooms
2.02.0 out of 10
1 review(1 review)
The current price is AU$429
AU$429
for 3 nights, 1 houseboat
AU$143 per night
includes taxes & fees
Book now, and make memories that will last a lifetime in the heart of Sarasota!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
The current price is AU$1,424
AU$1,424
for 3 nights, 1 home
AU$475 per night
includes taxes & fees
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
The current price is AU$2,143
AU$2,143
for 3 nights, 1 home
AU$714 per night
includes taxes & fees
Charming Studio Unit Across from Lido Key Beach
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
18 reviews(18 reviews)
The current price is AU$940
AU$940
for 3 nights, 1 apartment
AU$313 per night
includes taxes & fees
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