Holiday rentals with a fireplace in Bayshore Gardens

5 out of 5 average rating, 146 reviews

The Turtle Nest-Lanai w/Hot Tub+5mi to beach

🐢Come and relax at this peaceful, tropical, and romantic oasis. "The Turtle Nest" is a single family home located in the heart of Sarasota; only 5 miles to the Siesta Key Beach! It offers 3 bedrooms, 2 baths and can sleep up to 6. Picture a screened lanai, your own juicy star fruit, complete with a bubbling hot tub and a sizzling grill. The outdoor setting is private-the yard is surrounded by palms and fruit trees. Your stay here is destined to be a blend of comfort, delight, and rejuvenation.

Superhost

4.85 out of 5 average rating, 106 reviews

LUXE! Heated Salt POOL! Close to Town, Beach, IMG

Beautifully updated coastal farmhouse home in a quiet cul de sac with a private pool oasis in the back. The salt water pool is completely screened in so you can stay in the pool all day and night long without worrying about flies or mosquitos. Kitchen is fully stocked and ready for you to cook up a storm! Or if you prefer, downtown Sarasota is only a short 15 minute drive away with plenty of eating options. Siesta key beach is rated the number one beach in the USA and it’s only 30 minutes away!

4.95 out of 5 average rating, 131 reviews

Vacation Pool - House in Bradenton!

Welcome and enjoy a relaxing vacation house with your family. This heated POOL house is well situated and well-maintained in a cul-de-sac and is central to the beach (15 minute drive to Anna Maria Island), IMG Academy, The Bradenton Country Club, famous Riverwalk, downtown and numerous restaurants and shopping options. Enjoy your own private oasis with plenty of space for your family and friends with 3 bedrooms that can sleep 8 guests and a fourth bonus room that can sleep 2 additional guests

4.93 out of 5 average rating, 168 reviews

Chic Oasis-Backyard Goals-Game Room-Pup Haven-Pool

Step away from the ordinary into your chic escape! Styled in modern black & white with a trendy edge, it is the perfect backdrop for your insta-worthy stay. Rainy day? No problem - our game room is packed with hours of fun, friendly competition. Evenings made magical with a night cap swim, cozy fire, or oversized yard games. Don't forget your photo op with our angel wings mural - the ultimate backdrop for your memories. Your pup is welcome too! This isn't just a stay - it's a vibe.

Superhost

4.79 out of 5 average rating, 349 reviews

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

4.93 out of 5 average rating, 370 reviews

Home in Pelican Cove

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the pool and patio (renovated in July 2025) and comfy outdoor furniture in your fenced in backyard where you can bask in the sun. - Beautifully designed coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

4.96 out of 5 average rating, 307 reviews

Casa del Río! Beaches, IMG, Boating, and Riverwalk.

Welcome to "Casa del Rio" in Bradenton, FL featured in hit TV Show 90 DAY FIANCÉ! Location less than 15 minutes from the beach, IMG, Downtown, Riverwalk, Pirate City, and popular restaurants. Main Road takes you straight to Beach NO turns! I've thought of everything to make your stay as comfortable as possible. Keyless check-in experience with Smart Lock. Amazon Fire TV Free movies and TV Shows. Netflix ready. Brazilian Hammock under a Tiki Hut. Coffee and Tea station. Beach gear.

4.94 out of 5 average rating, 104 reviews

Luxury Heated Pool/ Family Home/Siesta Key-3BR/2BA

Welcome to your home away from home! This renovated, spacious and bright pool home will immerse you into a luxurious experience the minute you arrive. Located on a lush quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in USA), 10 minutes to downtown including fantastic restaurants and shopping and walking distance to the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake park and The new UTC mall!

4.95 out of 5 average rating, 128 reviews

Home in Arlington Park

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool.

4.99 out of 5 average rating, 142 reviews

Guesthouse in Sarasota

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

4.93 out of 5 average rating, 106 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

Charming 2BR/2BA Lakefront Home with Heated Pool – Just 2 Miles to Siesta Key Beach! Escape to this picturesque lakefront retreat, only 2 miles from the world-famous Siesta Key Beach. Perfect for families or groups, this spacious and beautifully furnished home offers a relaxing and memorable getaway. Lounge by the heated pool, soak in stunning lake views, or explore nearby attractions—this home is your ideal Sarasota vacation base.

Superhost