
Holiday rentals near Pioneer Park
We found 6,782 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:26 Sept - 3 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$5,391
NZ$5,391
NZ$770 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$2,067
NZ$2,067
NZ$295 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$3,105
NZ$3,105
NZ$444 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$2,049
NZ$2,049
NZ$293 per night
includes taxes & fees
Image gallery for The Sand Castle - Backyard Oasis Mins from Siesta!

1010 out of 10 rating
Exceptional
(7 reviews)
The Sand Castle - Backyard Oasis Mins from Siesta!
Sarasota, FL
9% off
Price is NZ$5,140
NZ$5,140
NZ$734 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$24,564
NZ$24,564
NZ$3,509 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$3,269
NZ$3,269
NZ$467 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
6% off
Price is NZ$3,724
NZ$3,724
NZ$532 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
(50 reviews)
Stunning Fully Remodeled House with Heated Pool! 30%OFF
Sarasota, FL
7% off
Price is NZ$2,626
NZ$2,626
NZ$375 per night
includes taxes & fees
Image gallery for Spacious and Bright Townhome on beautiful Longboat Key

9.69.6 out of 10 rating
Exceptional
(18 reviews)
Spacious and Bright Townhome on beautiful Longboat Key
Longboat Key, FL
8% off
Price is NZ$2,986
NZ$2,986
NZ$427 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
(28 reviews)
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Sarasota, FL
7% off
Price is NZ$3,561
NZ$3,561
NZ$509 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 NZ$1,587
NZ$1,587
NZ$227 per night
includes taxes & fees
Image gallery for The Bray Escape. 4.7 Miles to Siesta Key

1010 out of 10 rating
Exceptional
(11 reviews)
The Bray Escape. 4.7 Miles to Siesta Key
Sarasota, FL
7% off
Price is NZ$4,000
NZ$4,000
NZ$571 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$1,980
NZ$1,980
NZ$283 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
7% off
Price is NZ$3,656
NZ$3,656
NZ$522 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$2,025
NZ$2,025
NZ$289 per night
includes taxes & fees
Image gallery for Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage

9.89.8 out of 10 rating
Exceptional
(87 reviews)
Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage
Longboat Key, FL
7% off
Price is NZ$2,688
NZ$2,688
NZ$384 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$3,573
NZ$3,573
NZ$510 per night
includes taxes & fees
Image gallery for Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach

9.49.4 out of 10 rating
Exceptional
(133 reviews)
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Siesta Key, FL
7% off
Price is NZ$2,832
NZ$2,832
NZ$405 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 NZ$4,855
NZ$4,855
NZ$694 per night
includes taxes & fees
Image gallery for BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

9.69.6 out of 10 rating
Exceptional
(50 reviews)
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Sarasota, FL
7% off
Price is NZ$2,587
NZ$2,587
NZ$370 per night
includes taxes & fees
Image gallery for Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.49.4 out of 10 rating
Exceptional
(12 reviews)
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Siesta Key, FL
7% off
Price is NZ$3,866
NZ$3,866
NZ$552 per night
includes taxes & fees
Image gallery for Tranquil 3BR Retreat: Private Pool, Large Yard, Near Beach & Downtown.

1010 out of 10 rating
Exceptional
(7 reviews)
Tranquil 3BR Retreat: Private Pool, Large Yard, Near Beach & Downtown.
Sarasota, FL
7% off
Price is NZ$3,661
NZ$3,661
NZ$523 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$4,636
NZ$4,636
NZ$662 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Pioneer Park
THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW
Sleeps 4 · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
Swivel On Anchor
Sleeps 4 · 2 bedrooms
2.02.0 out of 10
1 review(1 review)
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
24 reviews(24 reviews)
Hibiscus Suites - Gateway to Siesta Key
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
2,137 reviews(2,137 reviews)
Beach Cottage with a Private Hot Tub
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
61 reviews(61 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
141 reviews(141 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