Vacation rentals near Pioneer Park
We found 6,920 vacation rentals — enter your dates for availability
Choose the perfect vacation home within close proximity to Pioneer Park. Vacation rentals provide the best amenities for your stay with friends, family, or just your pet, such as parking and air conditioning. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Pioneer Park
Showing deals for:Nov 14 - Nov 21
Image gallery for Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Bradenton, FL
10% off
Price is CA $337
CA $337
CA $3,232 total
CA $3,232 total
includes taxes & fees
Image gallery for Tranquil Pool Home Minutes to Siesta Key
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Tranquil Pool Home Minutes to Siesta Key
Sarasota, FL
5% off
Price is CA $233
CA $233
CA $2,663 total
CA $2,663 total
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
(12 reviews)
Charming Longboat Key Bungalow with private beach 5 min walk away
Longboat Key, FL
8% off
Price is CA $202
CA $202
CA $2,071 total
CA $2,071 total
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
10% off
Price is CA $268
CA $268
CA $2,552 total
CA $2,552 total
includes taxes & fees
Image gallery for Charming Chic Getaway - 2 min. Walk to Beach, Restaurants, & Shops
1010 out of 10 rating
Exceptional
(11 reviews)
Charming Chic Getaway - 2 min. Walk to Beach, Restaurants, & Shops
Siesta Key, FL
23% off
Price is CA $358
CA $358
CA $3,191 total
CA $3,191 total
includes taxes & fees
Image gallery for Stylish Retreat on Private Crescent Beach
1010 out of 10 rating
Exceptional
(96 reviews)
Stylish Retreat on Private Crescent Beach
Siesta Key, FL
10% off
Price is CA $429
CA $429
CA $3,960 total
CA $3,960 total
includes taxes & fees
Image gallery for Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
1010 out of 10 rating
Exceptional
(40 reviews)
Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
Sarasota, FL
10% off
Price is CA $474
CA $474
CA $4,339 total
CA $4,339 total
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
9% off
Price is CA $384
CA $384
CA $3,654 total
CA $3,654 total
includes taxes & fees
Image gallery for Your Beachside Retreat – Siesta Key’s White Sands Just Steps Away!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Your Beachside Retreat – Siesta Key’s White Sands Just Steps Away!
Siesta Key, FL
9% off
Price is CA $395
CA $395
CA $3,590 total
CA $3,590 total
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
10% off
Price is CA $418
CA $418
CA $3,835 total
CA $3,835 total
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
10% off
Price is CA $1,341
CA $1,341
CA $12,036 total
CA $12,036 total
includes taxes & fees
Image gallery for SARASOTA Heated Pool - Pet Friendly - Garage w/ EV Charger - Close to Beaches!
1010 out of 10 rating
Exceptional
(44 reviews)
SARASOTA Heated Pool - Pet Friendly - Garage w/ EV Charger - Close to Beaches!
Sarasota, FL
15% off
Price is CA $260
CA $260
CA $2,549 total
CA $2,549 total
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
9% off
Price is CA $391
CA $391
CA $3,677 total
CA $3,677 total
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
10% off
Price is CA $445
CA $445
CA $4,323 total
CA $4,323 total
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
10% off
Price is CA $248
CA $248
CA $2,295 total
CA $2,295 total
includes taxes & fees
Image gallery for Siesta Key Vacation Property W/Heated Pool and Beach Access
1010 out of 10 rating
Exceptional
(57 reviews)
Siesta Key Vacation Property W/Heated Pool and Beach Access
Siesta Key, FL
5% off
Price is CA $445
CA $445
CA $4,344 total
CA $4,344 total
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
(109 reviews)
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Siesta Key, FL
17% off
Price is CA $237
CA $237
CA $2,704 total
CA $2,704 total
includes taxes & fees
Image gallery for Charming Beach Cottage
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Charming Beach Cottage
Sarasota, FL
19% off
Price is CA $215
CA $215
CA $2,067 total
CA $2,067 total
includes taxes & fees
Image gallery for Siesta Key Beachside Condo-direct beach access
1010 out of 10 rating
Exceptional
(13 reviews)
Siesta Key Beachside Condo-direct beach access
Siesta Key, FL
10% off
Price is CA $408
CA $408
CA $3,752 total
CA $3,752 total
includes taxes & fees
Image gallery for Outdoor shower and wonderful private fenced yard
9.89.8 out of 10 rating
Exceptional
(78 reviews)
Outdoor shower and wonderful private fenced yard
Sarasota, FL
5% off
Price is CA $131
CA $131
CA $1,132 total
CA $1,132 total
includes taxes & fees
Image gallery for Lock in Sunshine and Savings Now
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Lock in Sunshine and Savings Now
Siesta Key, FL
6% off
Price is CA $458
CA $458
CA $4,798 total
CA $4,798 total
includes taxes & fees
Image gallery for Very tropical, private and peaceful, short walk to everything happening downtown
9.89.8 out of 10 rating
Exceptional
(56 reviews)
Very tropical, private and peaceful, short walk to everything happening downtown
Sarasota, FL
5% off
Price is CA $180
CA $180
CA $1,762 total
CA $1,762 total
includes taxes & fees
Image gallery for Updated and upgraded. Close to Beaches, Downtown, Hospital.
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Updated and upgraded. Close to Beaches, Downtown, Hospital.
Sarasota, FL
15% off
Price is CA $335
CA $335
CA $3,289 total
CA $3,289 total
includes taxes & fees
Image gallery for Luxury Family size house, 9 miles away from siesta key, with pool
1010 out of 10 rating
Exceptional
(13 reviews)
Luxury Family size house, 9 miles away from siesta key, with pool
Sarasota, FL
24% off
Price is CA $313
CA $313
CA $3,095 total
CA $3,095 total
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
27 reviews(27 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
9.49.4 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Top rated rentals - Pioneer Park
Great Find
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
This house is perfect . When we entered you could smell how clean it was ! It was so spacious even with 9 of us staying there. The pool area is gorgeous!Location Location Location. I would definitely recommend!!!!
Rhonda W.
Stayed May 2024
Siesta Key, best beach anywhere
1010 out of 10
Exceptionalexceptional
321 reviews(321 reviews)
Fabulous beach cottage. Nothing lacking, cozy, super clean, wonderful host . We will be back, loved every minute !
Elizabeth W.
Stayed May 2024
Lovely
1010 out of 10
Exceptionalexceptional
84 reviews(84 reviews)
The condo was very well stocked with everything you could ever need. Comfortable beds. We really appreciated having 2 beds in the one room so no one had to sleep on the couch.
Short walk to the beach. Convenient location. No complaints here
S P.
Stayed Jan 2024
As advertised
1010 out of 10
Exceptionalexceptional
148 reviews(148 reviews)
Great location, short walk to the beach. Quiet, peaceful area. Convenient parking.
Spacious living and sleeping area. Fully kitchen with everything you need. Chairs and umbrella for the beach and washing machines nearby if you need them.
The access to the beach puts you next to a resort so the crowds one would typically encounter on a public beach did not exist.
We will be returning as soon as we can!
Colin
Stayed Jul 2023
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, yards and more
More for lessMore space, more privacy, more amenities — more value