Holiday rentals with a pool in Pinecraft, Sarasota Springs

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Popular amenities for Pinecraft, Sarasota Springs rentals with a pool

House rentals with a pool

Guest favourite
Home in Sarasota
4.96 out of 5 average rating, 27 reviews

Welcome To Shoreline:4BR, Heated Pool, 7m -beach

JillRating, 5 stars1 week ago
Brandon was very responsive to a few things we needed help with on the first day. We enjoyed our stay in Sarasota and this home with two rooms to relax and unwind, in addition to 4 bedrooms was perfect for our group!
Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 54 reviews

Mauna Loa House

TammyRating, 5 stars1 week ago
Second time staying here, and it was just as lovely as the first! The location is perfect — close to beaches, restaurants, and shopping — making it a convenient spot for a relaxing getaway. Gosia was a wonderful host, always prompt in her responses and helpful with any questions we had. We’re looking forward to staying again in the future!
Superhost
Home in Sarasota
4.77 out of 5 average rating, 30 reviews

Salt Life Villa with heated pool & outdoor dining

GraciRating, 5 stars2 weeks ago
We had a fantastic stay at this Sarasota home! The 3-bedroom, 2-bath layout was perfect for our group, and the private pool was such a highlight. The house had everything we needed to cook at home, plus thoughtful extras like beach chairs, an umbrella, and a wagon for beach days. The host provided super clear instructions and helpful local recommendations, which made everything smooth and easy. We loved our time here and would absolutely recommend staying!
Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 58 reviews

GARDEN VIEW HOUSE WITH A POOL

KaileyRating, 5 stars2 weeks ago
This was a great home to stay at, our best Airbnb we've experienced so far! We had a 1yr old & 6yr old with us & it was set up perfectly. They had the pack n play (and high chair) all set up for us upon arrival which was much appreciated since travel with young kids is...a lot. The bin of wooden and Lego type blocks was so extremely helpful to entertain both kids, along with the smart tvs! We also greatly appreciated the beach gear. The home looked very clean & we loved the setup. Wonderfully stocked kitchen,bathrooms, etc. Finally, the neighborhood seemed decently quiet and peaceful. When the kids went to bed, my husband & I were able to hang out by the pool (loved the lights) and get some well needed down time just listening to the birds and crickets. We would absolutely select this home if/when we're back to the area. The beach was about 20min drive, probably the only downfall I can come up with, but it was such an easy drive & the home was so close to grocery stores etc. Thank you!
Guest favourite
Home in Sarasota
4.94 out of 5 average rating, 31 reviews

Golf Views +Swimming Pool & Hot Tub,Near Pinecraft

YoankaRating, 5 stars2 weeks ago
We had a wonderful weekend at the property. Everything was clean, well-maintained, and exactly as described. The location was peaceful and ideal for a relaxing getaway. The host was responsive and accommodating, making the entire experience smooth and enjoyable. We would definitely stay here again and highly recommend it to others.
Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 142 reviews

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

Brian M.Rating, 5 stars2 months ago
I’d highly recommend this home. Clean and spacious home, well stocked kitchen, and nice master bedroom and bathroom. Very nice pool and large outdoor patio area. Handy washer/dryer and beach cart/chairs/umbrella. Pretty easy to get to any place in Sarasota or Siesta Key that we wanted. We didn’t need much at all, but the host, Lana, was very responsive.
Guest favourite
Home in Sarasota
5 out of 5 average rating, 12 reviews

Hummingbird House - Pool & Games

KirstenRating, 5 stars3 weeks ago
beautiful house had so much fun
Guest favourite
Home in Sarasota
4.93 out of 5 average rating, 359 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

TerryRating, 5 stars2 weeks ago
This place was perfect for us. family of 4 with 2 kids age 7 and 10. They loved the pool which was bigger then it looked from the photos, was very warm and garden well maintained. really happy with stay and Carrick was quick to respond when we ask questions. asked for a later check out which Carrick was able to accommodate. Great stay would recommend.

Apartment rentals with a pool

Guest favourite
Apartment in Siesta Key
4.91 out of 5 average rating, 127 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

MariaRating, 5 stars1 week ago
Loved the location and the layout of the condominium! We will be coming back!
Top guest favourite
Apartment in Siesta Key
4.97 out of 5 average rating, 319 reviews

On the Beach; Siesta Key SunBum Studio

LauraRating, 5 stars2 weeks ago
My daughter and I stayed for a mother daughter girls trip and had a blast! They made sure to take care of every little detail to make you feel comfortable and at home. Even checking in and making sure we made it ok. It was very clean and the location was amazing. Easy to get around on the trolly if we didn't want to drive and literally steps away from the beautiful white sand and clear turquoise beach. Do yourself a favor and book the trip!
Guest favourite
Apartment in Siesta Key
4.9 out of 5 average rating, 119 reviews

Crystal House on Siesta Key Beach

BiancaRating, 5 stars1 week ago
We loooved it here! The space was perfect for our family. I cooked several meals and the kitchen had everything I needed. The location was convenient to grocery stores and walking distance to local restaurants and ice cream shops. The trolley stop is right at the resort so very convenient free rides to downtown Siesta Key was one of the highlights of our trip. We also grilled in the back of the resort by the bay which was nice! Oak trees all around. The pool was perfect temp. The fob didn’t work for one of the gates but there were three others we were able to get in without issue. The beds and pillows were soooo comfy. The ONLY issue we had was from the pics on the original post it appeared the walk to the closest public beach access was 2 min but it was actually 15. In the Florida heat that was rough but we pushed through! Oh and last thing, the scooters were a hit with everyone in our family. So much fun! 😆 Thank you so much for giving us an amazing stay!!
Superhost
Apartment in Lido Key
4.8 out of 5 average rating, 104 reviews

LIDO KEY 1 BR/1Bath Heated Pool 16

ChrisRating, 5 stars9 months ago
Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed
Guest favourite
Apartment in Sarasota
4.87 out of 5 average rating, 115 reviews

Anchor house +6 min. from Siesta Beach+heated pool

DianeRating, 5 stars3 days ago
The location was great. Easy access to the beach, grocery stores, restaurants and the pool. Doris was friendly and professional. The condo was very comfortable for my husband and I and our two grandsons. thank you, Doris. We had a wonderful time.
Guest favourite
Apartment in Bradenton Beach
4.88 out of 5 average rating, 121 reviews

Charming and Updated 1 Bedroom in Runaway Bay

MeleahRating, 5 stars3 weeks ago
My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!
Top guest favourite
Apartment in Longboat Key
4.98 out of 5 average rating, 186 reviews

Condo with a View 1: Open Friday, $250/nt!

AbigailRating, 5 stars1 week ago
This condo was everything I needed and more! The location? Absolutely perfect—the beach is literally your backyard. Waking up to that ocean view the next morning was a dream. Restaurants and activities were just minutes away, which made everything so easy and fun. Heidi, the host, went above and beyond. Her communication was fast, kind, and incredibly thoughtful. She even surprised us with a delicious key lime pie and orange juice waiting for us after jet skiing—such a sweet and personal touch! I truly have no complaints. Everything about this stay was peaceful, beautiful, and seamless. I’d absolutely recommend this spot to anyone looking for a relaxing and magical beach getaway. 🌴🌊💛
Guest favourite
Apartment in Siesta Key
4.94 out of 5 average rating, 108 reviews

Siesta Key Beach Front Condo

JenniferRating, 5 stars2 weeks ago
Another wonderful trip to Siesta! This is our third stay in one of Evan’s places, and we were not disappointed. This unit had a great view of the Gulf (this particular building has the most direct view, without the parking lot!), and the screened in lanai was amazing! As always, the unit was clean, well-stocked, and a perfect home away from home. Already counting down the days till we return!

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