Mansion holiday rentals in Siesta Key

A custom pool is framed by elegant lounge chairs and tropical landscaping. Water features create gentle curves, while illuminated details enhance the space as the sunset casts a warm glow. A covered outdoor area is visible in the background, providing seating and entertainment options.

4.99 out of 5 average rating, 79 reviews

Fruit /Botanical Garden Estate 2 ml to downtown EV

Indulge at this Mediterranean estate, boasting lush botanical gardens and rare tropical fruit trees for your picking pleasure. Enjoy the custom pool, hot tub, sauna, cold plunge and the home gym. The expansive outdoor haven features a fully-equipped kitchen, fireplace, TV, and dining space. Enjoy leisurely games of pool, ping pong & shuffleboard, then retreat to the luxurious indoors with comfortable beds and a massive TV, all within the privacy of a walled-in estate. Your lavish escape awaits.

Superhost

A heated pool is enclosed within a screened area, surrounded by lush greenery and outdoor seating. The pool area features a natural stone deck, with lounge chairs positioned for sunbathing. The peaceful environment offers a private retreat for relaxation and enjoyment.

4.91 out of 5 average rating, 106 reviews

Heated Pool - Just 1 mile to Beach! Updated/Fun!

Fun for the whole family!! Only 1 mile to the Beach! This newly updated home comes fully furnished with 4 bedrooms and 3 bathrooms. With a total of 6 beds, the home sleeps 10 comfortably. The Heated Pool is perfect for swimming, and being only 1 mile to the world famous Siesta Key Beach Access 12, this home also makes beach going easy and convenient. Inside, the home is clean, spacious and newly updated and equipped with smart tvs, air hockey table, pool table foose-ball, Pac-Man - fun for all

An indoor pool is enclosed within a screened area, offering a clear view of tranquil blue water and surrounding trees. Comfortable outdoor seating is visible, complemented by a sunlit patio space. Large glass doors provide access to the pool area, enhancing the open feel.

4.97 out of 5 average rating, 167 reviews

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

5 out of 5 average rating, 119 reviews

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

Villa in Arlington Park

Luxury Villa with Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

4.92 out of 5 average rating, 12 reviews

Home in Siesta Key

Spacious Siesta Key Home Private Pool-Beach 1 mile

Your Perfect Siesta Key Getaway Awaits! 🌴 Escape to paradise in this spacious three-level home, ideal for families seeking comfort, privacy, and a taste of Florida's coastal charm. Located just 1 mile from the pristine, world-famous Siesta Key Beach, you'll enjoy easy access to sun, sand, and surf. For your convenience, a complimentary shuttle picks you up right from the house, whisking you away to the beach or the charming Siesta Key Village for shopping, dining, and entertainment.

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 218 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

Home in Downtown Sarasota

4.93 out of 5 average rating, 46 reviews

Serenity Springs | Private Heated Pool + Waterfall

BNB Breeze presents Serenity Springs! Experience this stunning, peaceful oasis in the heart of Sarasota, located moments from the picturesque beaches! This home is Fully Loaded with awesome amenities. - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Whole home Water filtration system - Rooftop Perch (the Best sunsets) - Outdoor Dining and Sitting Areas - Outdoor Ping Pong Table - Breville Espresso Machine + Syrups - 2 Stunning floors of stylish design

5 out of 5 average rating, 36 reviews

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Arlington Park

Sarasota Escape | Minutes to Beaches + Downtown

HEATED POOL + ECO FRIENDLY. Relax with the whole family or bring that group chat trip to life at this peaceful retreat in the heart of Sarasota. Boasting a spacious and nature-inspired design, this home is a short drive to several world class beaches, the downtown Sarasota arts district, 5 star dining, shopping and more. The home is also located within walking distance of a park complete with playground, public pool, tennis + basketball courts, workout area and walking trails.

4.97 out of 5 average rating, 155 reviews

Home in Bradenton

SLeePs 18-JaCuZZi-2kingSuites-Pickleball-2babyCrib

We sleep 18 AND 2 baby crib MESSAGE ME FOR ADDITIONAL INFO 5 BEDROOMS!!! NEW PICKLEBALL COURT- new mini golf course- Kids playground- Hot tub- bunks with tube slide- Arcade room- pool table and more! ▪️2 Game Rooms ▪️2KingSuites ▪️7 miles to Beach ▪️Blackout curtains ▪️BabyMonitor▪️Crib AND Pack N Play ▪️HighChair ▪️beach chairs▪️pool table▪️hot tub ▪️pickleball▪️RokuTV’s▪️Self Checkin ▪️AirHockey ▪️Grill ▪️FirePit ▪️Washer/Dryer ▪️Coffee Bar▪️Cable ⭐️No Checkout List⭐️

4.95 out of 5 average rating, 181 reviews

Home in Bellevue Terrace

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! VR24-00264

4.97 out of 5 average rating, 183 reviews

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

Home in Bradenton Beach

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.