Holiday rentals with breakfast in Sarasota County

A cozy living area features a plush blue sofa and two accent chairs. Light filters through large windows adorned with navy blue curtains. A sleek coffee table is positioned in front of a wall-mounted television displaying a scenic image. A ceiling fan adds to the relaxed atmosphere.

4.73 out of 5 average rating, 15 reviews

Nottingham Beach Bungalow Near Siesta Key Beach!

This cozy Nottingham Beach Bungalow is in a central location to enjoy the best of Sarasota! With a large fenced-in yard, new sunroom with vinyl windows & AC/outdoor-style living-room , and a backyard firepit for a relaxing evening, we are here to help you have an amazing experience on & off the beach! Situated in a quiet residential cul-de-sac, you are only a few minutes drive to all of downtown Sarasota, 10 min to Siesta Key beach, & walkable to Trader Joe's, Walt's Fish Market & stores etc.

New place to stay

Retro Glam 5 Min to Downtown l Couples or Besties!

Vintage charm meets pop glam ✨ Near the best Southwest Florida hotspots! ✅ Main Street, Downtown Sarasota 2 miles - 6 mins ✅ St. Armand’s Circle: 4.5 miles - 15 mins ✅ Lido Key Beach 5 miles - 15 mins ✅ Siesta Key Beach: 6 miles - 18 mins ✅ Downtown Bradenton 12 miles - 25 mins ✅ Bradenton Beach 14 miles - 30 mins ✅ Casey Key 16 miles - 30 mins ✅ Airport: Sarasota–Bradenton International Airport 6 miles - 12 minutes

A screened lanai features a round glass table surrounded by four black chairs. Lush greenery is visible through the screens, providing a tranquil view of the outdoor area. Soft lighting fixtures hang from the ceiling, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 29 reviews

Beautiful Home in Gulf Gate 4 Miles to Siesta Key!

Beautiful, totally remodeled Gulf Gate Home 4 Miles To Siesta Key Beach. This home has beautiful natural light in every room and has been fully updated with a modern touch. Includes so many wonderful sitting areas: modern living room, screened lanai with dining table, Florida sunroom with amazing farm table and lounge sofa, outside patio with grill and chaise lounges. Walking distance to Gulf Gate Library, Gulf Gate Restaurants and Nightlife. No RVs, Boat, or Jet Skis are permitted.

A spacious living area features a stone fireplace framed by a wooden mantel. Comfortable seating is provided by a light-colored sofa and armchair, paired with a round coffee table positioned on a soft area rug. Natural light enters through multiple doors, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 147 reviews

Coastal Retreat Near Beaches

Unwind at this cozy 5 bedroom coastal retreat, just minutes from Sarasota’s top beaches like Siesta Key and Lido Beach. Ideal for travelers, this home combines comfort and convenience. Inside, you’ll find a bright, airy space with coastal charm, a fully stocked kitchen, high speed internet with access to Wi-Fi, smart TV, and comfy beds. Step outside to a private backyard—perfect for morning coffee, evening drinks, or soaking up the Florida sun. Book now and enjoy the best of Sarasota!

Top Guest favourite

A vibrant sunset is displayed across the sky, with hues of orange, pink, and purple blending seamlessly. Silhouettes of palm trees are seen in the foreground, framing the tranquil water below, which reflects the striking colors of the sky. Nearby structures are softly illuminated in the fading light.

Guest suite in Sarasota

SIP & RELAX SPECTACULAR SUNSETS CLOSE TO SIESTA

Walk the No 1 beach in America, watch dolphins, wake up to sunny blue skies and the breeze from the bay. Watch spectacular sunsets daily whilst sipping your cocktail. Host your destination wedding - additional arrangements & cost. Located on the inter coastal waterway, a peaceful cul da sac & neighborhood close to Siesta Key. Gaze at the water & garden, spot the dolphins & birdlife. Close proximity to fabulous restaurants, boat/kayak rentals, Siesta Key, Downtown, & St Armands Circle.

Top Guest favourite

Two horses stand close together in a spacious green pasture, sharing an intimate moment. The surrounding area is open, with trees framing the scene, creating a serene atmosphere that reflects the natural beauty of the property.

Campervan/RV in Sarasota

4.99 out of 5 average rating, 86 reviews

HOME HOME ON THE RANCH. SARASOTA FL.

My place is great for couples, solo adventurers, and business travelers. Who love the great outdoors and love nature at its best! Lots of wild life to enjoy including our horses, piggy Miss Daisy Mae, Chickens, and they will even share their organic eggs with you every morning 🐣All on our property. You are welcome to take photos to also share your awesome memories. Enjoy our fabulous sunsets!🌞walk our Canopy Roads, Myakka State Park, and The Crawling Museum. Entire home, Camper/RV

Townhouse in Port Charlotte

A tranquil bedroom is featured with green walls and a wooden bed frame, adorned with ocean-themed bedding. A nightstand holds a decorative lamp. An assortment of seashells and a starfish are showcased on the bedding, enhancing the coastal vibe.

4.95 out of 5 average rating, 117 reviews

Exotic Escape home! w/ Heated Pool & Luxurious Spa

Discover a relaxing, tropical lifestyle on Florida's Gulf Coast. Located in the center and boarder of North Port and Port Charlotte you are close to shopping, beaches, restaurants, game fishing, dinner theaters and golf courses. This home is the perfect combination of quiet beauty, lively activity and friends to share it with. So look no further! We have your perfect get away!

4.93 out of 5 average rating, 29 reviews

A screened lanai features a heated pool surrounded by patterned lounge chairs and umbrellas. Comfortable seating areas are positioned nearby, offering a relaxing space to enjoy the outdoors while providing partial shade.

Home in Port Charlotte

Waterfront Retreat, Heated Pool, Fishing

Step into your dream Florida escape! This 2021 gem offers waterfront living, a heated pool, and a treasure trove of amenities that'll make your heart sing. Dive into family fun by the water, relax in the heated pool, and indulge in a fully stocked haven designed just for you. ◈Experience Port Charlotte With Us & Learn More Below!◈

4.97 out of 5 average rating, 74 reviews

A spacious boat seating area offers comfort while cruising on the water, with views of the waterfront community in the background. Adjacent is a heated pool with clear blue water, surrounded by a tiled deck and inviting steps leading in.

Home in Port Charlotte

House With A Boat–Your Private Waterfront Resort

Imagine this: your own private house, your own private dock, and your own private boat — no marinas, no lines, no sharing. If you love boating, fishing, and floating in the pool while the kids chase lizards and cannonball into the water, House With A Boat is your dream escape. Perfect for the Captain and crew — yes, kids included.

5 out of 5 average rating, 14 reviews

A newly constructed home is situated on a spacious lot, surrounded by lush greenery and mature trees. The driveway leads directly to a two-stall garage, with a clean, modern facade visible against a bright, open sky.

Home in Port Charlotte

Port Charlotte Tropical vacation home

Welcome to this brand new vacation home in Port Charlotte!! Bring your whole family and relax in this beautiful city. 3 Bedroom 2 bath home is conveniently located 15 -35 minutes from finest beaches, Great restaurants, shopping and golf courses are in the area. Take advantage of visiting the Warm Minerals Spring Park.

A tranquil outdoor space features a cocktail pool surrounded by a screened enclosure, with lounge chairs positioned nearby. A large umbrella provides shade, while an expansive view of a peaceful canal and lush greenery is visible in the background.

Home in Nokomis

Gulf Beaches Retreat

The whole group will enjoy easy access to Gulf beaches like Siesta Key, Nokomis, and Venice Beach . This home has coastal decor with a cozy vibe. You’ll love the cocktail pool and workout facility year round. Behind this retreat is a peaceful canal with a beautiful view of nature. This home is relaxing and welcoming.