Holiday rentals with outdoor seating in Sarasota

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to Mi Casa Siesta on Siesta Key, the #1 beach in the country! Gorgeous newly renovated one-bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

[The Bay St. Hideaway]Private Swimming Pool& Patio

Welcome to Bay Street Hideaway VR24-00156 A beautiful home to make your next family vacation the best one yet! The whole group will enjoy easy access to everything from this centrally located place. The patio fenced in backyard with a private HEATED pool provides a quiet and peaceful area if you want to avoid the crowds.The house is a 2 story completely furnished with 4 bedrooms and 3.5 bathrooms. TV's are provided in the living room, a few bedrooms, and lounge area upstairs. 3 E-bikes included

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!

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

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

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.

Casa de Zara| Downtown Sarasota- 5mi Lido Beach

Welcome to Casa de Zara! Immerse yourself in Sarasota history by staying in our quaint Adobe style home built in 1925 with a serene garden filled with plants and trees native to Florida. You will be 1 mile from Main St. and 4 miles to Lido Key. One block over you will find a fun filled park with tennis and pickle ball courts, a walking path and basketball courts. Less than a mile away is Bayfront Park which is perfect for watching sunsets!

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area has to offer. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

Luxury Pool Family Paradise-Siesta Beach Beach

Discover your exquisite home away from home! This beautifully renovated pool home offers ample space and natural light, ensuring a luxurious experience from the moment you step inside. Nestled on a serene street, it provides easy access to Sarasota's top attractions. With proximity to Siesta Key Beach, downtown, and the renowned Fresh Fish Waltz Market, you'll have an unforgettable stay.

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

Near Lido Beach w Hot tub + Fire Pit

Come find a space away in this 2 bedroom 2 bathroom Guest House with a backyard pergola located less than 15 Minutes from Lido Beach in Sarasota. Enjoy all that the area has to offer, and come home to the peaceful ambience of a hot tub and outdoor fire pit. The home is in a safe and friendly neighborhood, with the Legacy Bike Trail right around the corner

St Armand's Mid-Century Oasis

Mid-century retreat in the heart of Lido Key! Stroll to pristine beaches or enjoy the vibrant shops & eateries of St. Armand's Circle just steps away! Recently renovated with authentic period details, this 3BR/3BA gem boasts a sparkling pool, sun-soaked rooftop deck and stylish office. VR2400013