
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 NZ$5,331
NZ$5,331
NZ$762 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 NZ$3,323
NZ$3,323
NZ$475 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 NZ$2,125
NZ$2,125
NZ$304 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 NZ$2,026
NZ$2,026
NZ$289 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 NZ$2,405
NZ$2,405
NZ$344 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 NZ$1,848
NZ$1,848
NZ$264 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 NZ$2,328
NZ$2,328
NZ$333 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 NZ$5,143
NZ$5,143
NZ$735 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 NZ$24,291
NZ$24,291
NZ$3,470 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 NZ$3,756
NZ$3,756
NZ$537 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 NZ$3,022
NZ$3,022
NZ$432 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 NZ$3,872
NZ$3,872
NZ$553 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$13,532
NZ$13,532
NZ$1,933 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 NZ$2,597
NZ$2,597
NZ$371 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
8% off
Price is NZ$2,117
NZ$2,117
NZ$302 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 NZ$3,178
NZ$3,178
NZ$454 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$3,533
NZ$3,533
NZ$505 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 NZ$3,124
NZ$3,124
NZ$446 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 NZ$3,310
NZ$3,310
NZ$473 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
7% off
Price is NZ$5,713
NZ$5,713
NZ$816 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 NZ$1,822
NZ$1,822
NZ$260 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 NZ$2,003
NZ$2,003
NZ$286 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 NZ$3,571
NZ$3,571
NZ$510 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 NZ$4,865
NZ$4,865
NZ$695 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: 28 Sept - 1 OctSwivel On Anchor
Sleeps 4 · 2 bedrooms
2.02.0 out of 10
1 review(1 review)
The current price is NZ$461
NZ$461
for 3 nights, 1 houseboat
NZ$154 per night
includes taxes & fees
THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW
Sleeps 4 · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
The current price is NZ$1,641
NZ$1,641
for 3 nights, 1 apartment
NZ$547 per night
includes taxes & fees
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)
The current price is NZ$1,508
NZ$1,508
for 3 nights, 1 home
NZ$503 per night
includes taxes & fees
Hibiscus Suites - Gateway to Siesta Key
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
2,141 reviews(2,141 reviews)
The current price is NZ$667
NZ$667
for 3 nights, 1 room
NZ$222 per night
includes taxes & fees
Last Hoorah
Sleeps 4 · 1 bedroom
2.02.0 out of 10
3 reviews(3 reviews)
The current price is NZ$576
NZ$576
for 3 nights, 1 houseboat
NZ$192 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 NZ$1,540
NZ$1,540
for 3 nights, 1 home
NZ$513 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