Holiday rentals with a pool in Pinecraft

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with wood floors and lots of natural light, located in a quiet neighborhood on the downtown core edge. Enjoy a spacious and private, fenced-in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

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

Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.

Salt Water Pool on Golf Course

WELCOME TO OUR RETREAT! YOU'LL LOVE OUR OPEN-CONCEPT HOME. THE LR HAS A SINKING SOFA & CHAIR, TV WITH SOUND BAR, A DEDICATED WORK TABLE. THE NEW KITCHEN IS IDEAL FOR SOCIALIZING AND COOKING. GET COZY IN THE FR WITH THE COMFY SOFA BED SECTIONAL, FIREPLACE, AND ANOTHER SMART TV. WHEN IT IS TIME TO SETTLE IN, YOU WILL LOVE THE MBR AND MBA WITH THE 9 FT SHOWER WITH MULTIPLE SHOWER HEADS. POOL IS SO INVITING!! **ONLY 1 GROUP/STAY ALLOWED PER MONTH, HOST CALENDAR TO BE UPDATED AFTER BOOKING**

Sarasota Paradise/Stunning Home/Heated Pool

Bring the whole family. This home has lots of things for a fun vacation. Make great memories as you entertain in the lg kitchen, grab some coffee at the bar, sit on the patio and enjoy the beautiful view. Enjoy a walk or bike ride on the nearby Legacy Trail. Let this be a place where you experience the Blessings of God and be refreshed by His Grace as you spend time in our home away from your home. No pets! Beaches: - Siesta Key Beach, 7.7 mi. - Lido Key/St Armand’s Circle, 7.5 mi.

The Wisteria Oasis W/ heated pool & hot tub

Come Relax with your family at this peaceful 3 bedroom cottage, It has a private fenced in backyard w/ new heated saltwater pool, hot tub, hammock & swings,and a fire pit to make s’mores! Yes its stocked with beach gear and a short drive to the beautiful siesta key and lido key beaches. Also minutes from the Bayfront park where u can watch amazing sunsets and the downtown sarasota dining spots! Arlington park is in the neighborhood with trails- play area- pool- outdoor gym.

La Hacienda / heated pool, hot tub, 6 mi to beach

Experience the allure of La Hacienda, a charming rental with a warm Southwestern-inspired interior with unique touches. This 4-bedroom, 2-bath home features a spacious living room with comfortable seating and multiple smart TVs. The private backyard awaits with a heated pool and hot tub for ultimate relaxation and entertainment. Located near downtown, you'll have easy access to beaches and dining. Indulge in the perfect blend of chillin', grillin' and sippin' at La Hacienda!

Coastal Getaway *With Bikes & NEW Saltwater Pool*

Just outside of Downtown near the Legacy Trail, this home is located in a quiet neighborhood only 15 minutes from the Siesta Key Beach. The home stands out with its bright and airy design, brand new saltwater pool in the private backyard, and its breezy living room. The large master bathroom rain shower is perfect to wash off the leftover sand from the beach. You can also spend your evenings grilling out back or playing corn hole in the patio area.

Luxury Pool Family Paradise-Siesta Beach/DT-3BR/2B

Welcome to your private oasis! This stunning pool home has undergone a meticulous renovation, offering a spacious and luminous retreat. Nestled on a serene street, it provides a peaceful escape while being in close proximity to Sarasota's top destinations. Whether you're seeking the sun-kissed shores of Siesta Key Beach, the vibrant downtown scene, or the flavors of the Fresh Fish Waltz Market, this home offers easy access to it all.

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!