Holiday rentals with outdoor seating in Sarasota County

Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta

BRAND NEW home centrally located in the highly sought-after neighborhood of Arlington Park 2 miles to downtown. Coastal Luxe is a 2 story single family home with an open floor plan with bright, warm and inviting areas for gathering, entertaining, & relaxation. Every room in the house thoughtfully designed for your comfort & enjoyment. Perfect for your large group of friends & family!. Pool & Spa, Outdoor kitchen equipped with gas grill & smoker Enjoy your own mini golf experience with 4 holes

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

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

Your Modern Beachside Getaway!

Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House, a beautifully curated Sarasota retreat designed for relaxation, comfort, inspiration, and quality time together. Enjoy a heated pool & spa, lush lanai, bright designer interiors, and a peaceful residential setting just 15 minutes from Siesta Key, Lido Key, and downtown Sarasota. Thoughtfully maintained and enjoyed by our family throughout the year, this home is ideal for couples, families, and discerning travelers seeking a restful and memorable getaway.

Heated&Renovated Pool•Beach Retreat•15m to Siesta

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

The Siesta Key Retreat - An Island Garden Oasis!

Your family will be close to everything when you stay at this centrally-located place on Siesta Key while still enjoying the private garden oasis this home has to offer. Just steps from the quaint shell beach or a bike ride to the beautiful sand of Siesta Key beach to spend the day or venture to the cool vibes of Siesta Key Village for dinner and shopping!. Additionally, you're only a few miles from the vibrant downtown Sarasota and St. Armand's Circle (26-VR-000095)

Luxury Pool Family Paradise-Siesta Key Beach/DT

Prepare to be enchanted by your new sanctuary! Immerse yourself in luxury at this spacious and bright pool home, recently renovated to perfection. Located on a peaceful street, it strikes the perfect balance between tranquility and convenience, with easy access to Sarasota's finest attractions. Unwind at Siesta Key Beach, indulge in downtown's culinary delights and shopping, and explore the famous Fresh Fish Waltz Market-all just minutes away!

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

Family-Friendly 3BR Home w/ Private Heated Pool, Hot Tub & Backyard– Near Siesta Key! Located just minutes from world-famous beaches, and a wide variety of dining, shopping, and entertainment options, this home is the perfect base for your Sarasota vacation. Whether you’re planning a family trip, a couples’ retreat, or a friends’ getaway, you’ll love the blend of comfort, convenience, and fun!