Holiday houses in Pinecraft

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Top-rated holiday rentals in Pinecraft

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
Apartment in Sarasota
4.82 out of 5 average rating, 22 reviews

Pinecraft 2BR Retreat • Minutes to Siesta Key

Spacious 2BR/1BA cottage in Sarasota’s charming Pinecraft neighborhood. Under new ownership with upgrades underway to improve comfort, amenities, and guest experience. Includes queen bed, second bedroom, full kitchen, private entry, and shared laundry. Walk to restaurants and markets. Just minutes from beaches, downtown, and family-friendly attractions. Perfect for small families or couples traveling together. Your family will be close to everything when you stay at this centrally-located place.

Top Guest favourite
Home in Sarasota
4.96 out of 5 average rating, 54 reviews

Welcome to Your Sarasota Escape!

Bright 3BR/2BA home just minutes from Sarasota’s best beaches! Enjoy a spacious yard, ample parking, and a quiet neighborhood close to Siesta Key, St. Armands, downtown, golf, dining, and shopping. Comfortable, convenient, and perfectly located for your Sarasota getaway. You’ll also enjoy quick access to Roger’s, der Dutchman, Yoders and anything you need to make your stay enjoyable. Whether you’re here for sunshine, food, or relaxation, this home is the perfect base for your Sarasota adventure

Top Guest favourite
Home in Sarasota
4.95 out of 5 average rating, 198 reviews

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

Top Guest favourite
A private driveway is framed by wooden fences, leading to a residence. Sunlight filters through the nearby palm trees, creating dappled shadows on the gravel surface. The entrance is marked by a wooden gate, adding a sense of privacy to the space.
Apartment in Sarasota
5.0 out of 5 average rating, 31 reviews

Botanical Bungalow at THE BAY

Keep it simple at this peaceful and centrally-located private apartment. The entire apartment is yours, with your own private driveway and entrance. Enjoy complementary bikes on the Legacy trail, just a few feet away. Pack your car with one of our coolers and some beach floats and travel less than 5 miles to Lido beach, or under 20 minutes to popular Siesta Key Beach. With your own bathroom, washer/dryer, and full kitchen, you'll have everything you need to make your stay enjoyable.

Top Guest favourite
Home in Sarasota Springs
4.83 out of 5 average rating, 41 reviews

Quiet Family Home w/ Pool Near Pinecraft

Escape to a serene family retreat near Pinecraft and Yoders! This 3-bed, 2-bath home features a screened-in heated swimming pool for year-round enjoyment. Nestled in a quiet, family-friendly neighborhood, savor nearby Amish dining at Yoders and Der Dutchman. Siesta Key & Lido Key Beaches are only 8.7 miles away! Explore Marina Jack's at Bayfront Park in downtown Sarasota, where you can admire stunning boats and enjoy a leisurely stroll. Your perfect vacation awaits you!

Guest favourite
A light-colored bedroom features a plush queen bed with a textured quilt and decorative pillows. A round stool sits at the foot of the bed, and a bedside table with a lamp is positioned beside it. An abstract artwork adorns the wall, adding a modern touch.
Apartment in Sarasota
4.83 out of 5 average rating, 107 reviews

Walk to Coffee, Parks, Ice Cream, & Pizza

Welcome to your perfect getaway destination – The Coconut Palm! Meticulously remodeled and tastefully decorated with your comfort in mind, this stunning one-bedroom apartment boasts a sumptuous queen-sized bed, ensuring a restful night's sleep. Rest easy knowing that cleanliness is our top priority – The Coconut Palm is professionally cleaned on a regular basis after every stay, guaranteeing a pristine environment for your enjoyment.

Top Guest favourite
Home in Sarasota
4.98 out of 5 average rating, 96 reviews

Ocean Breeze

Bring the whole family to this great place with lots of room for fun. The home has everything you need for a fun vacation. The house has an open feel with spacious living area. There is also outside seating. We are nestled in the heart of the quaint Pinecraft community. We are 10 Minutes to downtown Sarasota. Our place is 7.7 miles from Siesta Key Beach and 6.4 miles to Lido Key Beach/St Armand’s Circle.

Top Guest favourite
Apartment in Sarasota
5.0 out of 5 average rating, 18 reviews

Hacienda Hideaway

Escape to sunny Sarasota! This cozy 1-bedroom apartment in the charming Pinecraft neighborhood sleeps up to 4 with a queen bed and pull-out couch. Enjoy a full kitchen, private washer and dryer, fast WiFi, and a peaceful screened patio for morning coffee or evening relaxation. Just 15 minutes from Sarasota’s beautiful beaches. Private parking and electronic keyless entry included. 🌴☀️

Guest favourite
A covered patio area is visible beside a heated pool, featuring comfortable seating and a dining set. Large glass doors open to the interior, with ambient lighting illuminating the space. A clock is mounted on the wall, and lush greenery adds a natural touch.
Home in Sarasota Springs
4.9 out of 5 average rating, 205 reviews

Charming Sarasota Home with Pool!

Charming 3/2 home with a pool! very safe neighborhood, 8.9 miles to Siesta Beach and 5.5 miles to Lido Beach. 15 minute walk to The quaint little village of Pinecraft and Der Dutchman Restaurant and more restaurants and shops. Very clean, private back yard, heated pool, coffee station... really everything you need for a relaxing and enjoyable stay in Sarasota.

Guest favourite
The outdoor area features a heated pool surrounded by lounge chairs, providing ample space for relaxation. A dining set is positioned nearby, accompanied by an umbrella for shade. Lush greenery and palm trees border the property, complementing the serene atmosphere.
Home in Sarasota
4.91 out of 5 average rating, 122 reviews

Rhodes Retreat - Beautiful Pool and Backyard Space

Bright and newly renovated home for a delightful family escape in Sarasota. Central location near beaches, shopping, and downtown, yet nestled in a serene neighborhood. Short walk to charming Amish Village of Pinecraft. Ample parking, garage, and spacious front yard. Option to book separate secondary unit. Siesta Beach 8.7mi, Lido 5.8mi. VR24-00264

Top Guest favourite
A modern kitchen is displayed with a large wooden dining table surrounded by six rattan-style chairs. Two woven pendant lights hang above the table. Stainless steel appliances and wood shelving are visible, and sliding glass doors lead to a green outdoor space.
Home in Sarasota Springs
4.99 out of 5 average rating, 104 reviews

Palm Tree Haven

Enjoy our home tucked away in a small Florida neighborhood. Sit out in the screened in porch and enjoy the warm breeze. Less than 10 miles away from Lido and Siesta Key Beach and 5.5 miles away from Sarasota downtown this location gives you choices for a day on the beach or an dining out at one of Sarasota's many delicious restaurants.

Guest favourite
Home in Sarasota
5.0 out of 5 average rating, 6 reviews

Estrada Cottage #10

Relax and unwind in this quaint, cozy home perfectly nestled in the center of Pinecraft. Ideal for couples, our charming space offers comfort, simplicity, and the warmth of a peaceful neighborhood. Enjoy easy walks to local shops, bike paths, and delicious eateries—everything you need is just steps away.

Popular amenities for Pinecraft holiday rentals