Holiday rentals near Pioneer Park
We found 7,288 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:10 Apr - 17 Apr
Image gallery for Heated Pool + Game Room + Sleeps 12 +12 min Beach
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Heated Pool + Game Room + Sleeps 12 +12 min Beach
Sarasota
5% off
Price is NZ$7,518
NZ$7,518
for 7 nights, 1 home
NZ$1,074 per night
includes taxes & fees
Image gallery for Oceanfront home w/sunset views of Sarasota Bay
9.89.8 out of 10, Exceptional, (121 reviews)
Exceptional
(121 reviews)
Oceanfront home w/sunset views of Sarasota Bay
Sarasota
8% off
Price is NZ$8,255
NZ$8,255
for 7 nights, 1 home
NZ$1,179 per night
includes taxes & fees
Image gallery for Peaceful Riverfront Oasis with Private Island
1010 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)
Peaceful Riverfront Oasis with Private Island
Bradenton
8% off
Price is NZ$3,678
NZ$3,678
for 7 nights, 1 room
NZ$525 per night
includes taxes & fees
Image gallery for Tropical Backyard Oasis! Prime Location Near Main St & Trolley to Lido Beach!
1010 out of 10, Exceptional, (123 reviews)
Exceptional
(123 reviews)
Tropical Backyard Oasis! Prime Location Near Main St & Trolley to Lido Beach!
Sarasota
8% off
Price is NZ$3,976
NZ$3,976
for 7 nights, 1 home
NZ$568 per night
includes taxes & fees
Image gallery for Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)
1010 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)
Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)
Sarasota
7% off
Price is NZ$3,226
NZ$3,226
for 7 nights, 1 home
NZ$461 per night
includes taxes & fees
Image gallery for Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Siesta Key
8% off
Price is NZ$6,364
NZ$6,364
for 7 nights, 1 apartment
NZ$909 per night
includes taxes & fees
Image gallery for Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees
9.89.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees
Sarasota
5% off
Price is NZ$5,051
NZ$5,051
for 7 nights, 1 home
NZ$722 per night
includes taxes & fees
Image gallery for Coastal modern POOL home
9.89.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Coastal modern POOL home
Sarasota
8% off
Price is NZ$4,097
NZ$4,097
for 7 nights, 1 home
NZ$585 per night
includes taxes & fees
Image gallery for SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE
9.29.2 out of 10, Wonderful, (11 reviews)
Wonderful
(11 reviews)
SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE
Sarasota
8% off
Price is NZ$6,735
NZ$6,735
for 7 nights, 1 home
NZ$962 per night
includes taxes & fees
Image gallery for 3 Bedroom 2 1/2 bath House on the Grand Canal w/ heated pool & hot tub.
9.89.8 out of 10, Exceptional, (83 reviews)
Exceptional
(83 reviews)
3 Bedroom 2 1/2 bath House on the Grand Canal w/ heated pool & hot tub.
Siesta Key
5% off
Price is NZ$8,358
NZ$8,358
for 7 nights, 1 home
NZ$1,194 per night
includes taxes & fees
Image gallery for Location, Location Trolley to Beach, Walk Downtown. Bike Legacy Trail, Pets OK.
1010 out of 10, Exceptional, (117 reviews)
Exceptional
(117 reviews)
Location, Location Trolley to Beach, Walk Downtown. Bike Legacy Trail, Pets OK.
Sarasota
8% off
Price is NZ$3,581
NZ$3,581
for 7 nights, 1 home
NZ$512 per night
includes taxes & fees
Image gallery for Beach-Themed Cozy Cottage Close to Downtown, Beaches, Pinecraft & Legacy Trail!
9.09.0 out of 10, Wonderful, (6 reviews)
Wonderful
(6 reviews)
Beach-Themed Cozy Cottage Close to Downtown, Beaches, Pinecraft & Legacy Trail!
Sarasota
8% off
Price is NZ$2,858
NZ$2,858
for 7 nights, 1 cottage
NZ$408 per night
includes taxes & fees
Image gallery for Comfortable home, heated salt-cell pool with child-safety, 10 min from the beach
9.89.8 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
Comfortable home, heated salt-cell pool with child-safety, 10 min from the beach
Sarasota
8% off
Price is NZ$3,068
NZ$3,068
for 7 nights, 1 home
NZ$438 per night
includes taxes & fees
Image gallery for Adorable Lido Beach Home- walk to beach and St. Armand's
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Adorable Lido Beach Home- walk to beach and St. Armand's
Sarasota
8% off
Price is NZ$5,729
NZ$5,729
for 7 nights, 1 home
NZ$818 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, Exceptional, (43 reviews)
Exceptional
(43 reviews)
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Sarasota
7% off
Price is NZ$4,952
NZ$4,952
for 7 nights, 1 home
NZ$707 per night
includes taxes & fees
Image gallery for Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach
Sarasota
8% off
Price is NZ$4,576
NZ$4,576
for 7 nights, 1 room
NZ$654 per night
includes taxes & fees
Image gallery for Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Siesta Key
8% off
Price is NZ$6,418
NZ$6,418
for 7 nights, 1 apartment
NZ$917 per night
includes taxes & fees
Image gallery for Heated Private Pool! Recently Updated! Well Stocked Property! Mins to Beach
1010 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
Heated Private Pool! Recently Updated! Well Stocked Property! Mins to Beach
Sarasota
8% off
Price is NZ$4,567
NZ$4,567
for 7 nights, 1 home
NZ$652 per night
includes taxes & fees
Image gallery for A Whale of a Good Time!
1010 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
A Whale of a Good Time!
Sarasota
8% off
Price is NZ$6,383
NZ$6,383
for 7 nights, 1 home
NZ$912 per night
includes taxes & fees
Image gallery for Lavish Waterfront Condo: Heated Pools~Lanai~WiFi! By IMG~Beaches~AMI~Restaurants
1010 out of 10, Exceptional, (120 reviews)
Exceptional
(120 reviews)
Lavish Waterfront Condo: Heated Pools~Lanai~WiFi! By IMG~Beaches~AMI~Restaurants
Bradenton
7% off
Price is NZ$2,815
NZ$2,815
for 7 nights, 1 apartment
NZ$402 per night
includes taxes & fees
Image gallery for Charming Longboat Key Bungalow with beach access minutes away…
9.49.4 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Charming Longboat Key Bungalow with beach access minutes away…
Longboat Key
7% off
Price is NZ$3,205
NZ$3,205
for 7 nights, 1 apartment
NZ$458 per night
includes taxes & fees
Image gallery for Downtown Sarasota Florida Vacation Rental, Pet-Friendly 3BR/2BA,Close to Beaches
8.48.4 out of 10, Very good, (15 reviews)
Very good
(15 reviews)
Downtown Sarasota Florida Vacation Rental, Pet-Friendly 3BR/2BA,Close to Beaches
Sarasota
7% off
Price is NZ$1,808
NZ$1,808
for 7 nights, 1 home
NZ$258 per night
includes taxes & fees
Image gallery for Downtown Sarasota Florida Vacation Rental 3BR House, Pet-Friendly, Near Beaches
8.08.0 out of 10, Very good, (9 reviews)
Very good
(9 reviews)
Downtown Sarasota Florida Vacation Rental 3BR House, Pet-Friendly, Near Beaches
Sarasota
7% off
Price is NZ$1,808
NZ$1,808
for 7 nights, 1 home
NZ$258 per night
includes taxes & fees
Image gallery for Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”
1010 out of 10, Exceptional, (56 reviews)
Exceptional
(56 reviews)
Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”
Siesta Key
8% off
Price is NZ$4,973
NZ$4,973
for 7 nights, 1 apartment
NZ$710 per night
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
2,226 reviews(2,226 reviews)
Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
9 reviews(9 reviews)
Pelican Post at Anna Maria Island Inn
Sleeps 6 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
336 reviews(336 reviews)
Siesta Key Island Rentals
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
55 reviews(55 reviews)
Swivel On Anchor
Sleeps 4 · 2 bedrooms
2.02.0 out of 10
2 reviews(2 reviews)
Charming Mobile Home - Minutes to the white sandy beaches of Anna Maria Island!
Sleeps 4 · 2 bedrooms · 1+ bathroom
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