Holiday rentals with breakfast in Sarasota County

4.64 out of 5 average rating, 11 reviews

Guesthouse in Sarasota

Coastal Cottage near Siesta Key Beach

Welcome to Robinhood's, Lil John Coastal Cottage! Cozy & modern, it's a perfect get-away! With a large fenced yard, outdoor dining table & umbrella for 4, a screened in porch area, & firepit for relaxing evenings, you will have an amazing Sarasota experience both on and off the beach! Located on a quiet cul-de-sac street. that is walkable to restaurants, shops, grocery stores, and right across the bridge from Siesta Key (5 miles to the beach)! We're pet friendly for furry friends under 50lbs!

4.93 out of 5 average rating, 27 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.

5 out of 5 average rating, 9 reviews

Split Leaf Suite Amazing Pool, Hot Tub

Property Highlights • 5 Minute Walk to Beach (800ft) 5-10 Minutes to Village • Shared Heated Resort style Pool, Water Feature & Garden • 1 Bedroom, Bathroom, Living Room & Full Kitchen • 1 Queen Bed & Queen Sleeper Sofa (sleeps 4) • Outdoor Lounge Dinning Table for 8, Fire Table, Ice Maker, 2 Kayaks  • Clubhouse 1 w Ping Pong, Pool, Foosball, Pac-Man, Games • Starter Kit of Toiletry & Home Essentials • Free Private Parking, Laundry & Beach Essentials (Towels, Chairs, Cart, Umbrella)

Top Guest favourite

5 out of 5 average rating, 16 reviews

Tranquil Pool Home Minutes to Siesta Key

Welcome to The Summer Breeze Cottage! This adorable pool home offers everything you will need to have an amazing vacation in one of the most sought-after travel destinations! So, if you are ready to take a plunge in the private pool or relax poolside sipping a cool drink as you enjoy time making memories with family and friends, then this is the place for you! And when you're ready to explore you are minutes to Siesta Key Beach as well as the shops and restaurants of Gulf Gate Village.

New place to stay

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!

4.96 out of 5 average rating, 28 reviews

Condo in Sarasota

Beautiful lakeview 2 bedroom 2 bathroom condo

Welcome to a private oasis with wi-fi connectivity Relax in the air conditioned Lanai with lake views Just 3 miles from the world-famous Siesta Key Beach & sunset This clean 2nd floor condo has ceramic tile floors throughout, open floor plan with large tv, master bedroom with king size bed and enclosed lanai with full view of the lake When the weather permits just open sliding doors on the lanai to enjoy the fresh breeze! Check out various birds, turtles in their private sanctuary

Top Guest favourite

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

4.92 out of 5 average rating, 13 reviews

Fire Pit+BBQ | Outdoor Showers, Bikes & Beach Gear

Experience a Sarasota retreat designed for families, groups, and retreats. Just 3 miles from downtown and 12 minutes to Lido Beach, our modern farmhouse villa offers spacious bedrooms, a gourmet kitchen, and cozy lounges. Outdoors, enjoy a private patio with a fire pit, hammock, BBQ, and access to a large shared yard with dual showers and a bounce pad. Bikes, beach gear, EV charger, and kid‑friendly touches make every stay effortless, while thoughtful extras set us apart.

Home in Siesta Key

Sunnyside Up Cottage - Walk to Siesta, Waterfront

Welcome to your dream getaway on Siesta Key! This beautifully appointed, fully renoavted 3-bedroom, 3-bathroom waterfront home offers the perfect blend of comfort, luxury, and island living. Nestled on a quiet canal just minutes from the world-renowned Siesta Beach, this private retreat is ideal for families, couples, or boating enthusiasts. Pet Friendly - all pets must be approved by management. Pet Fee $250.

Townhouse in Port Charlotte

4.95 out of 5 average rating, 114 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!

4.81 out of 5 average rating, 140 reviews

Vacation Paradise Close to Beach!

Totally remodeled fantastic vacation spot with a luxurious screened in private heated pool - this spacious house has all the amenities of home so you'll never want to leave! Just a quick 7-10 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St Armand's Circle with tons of shops and restaurants!