Holiday rentals with breakfast in Sarasota County

4.75 out of 5 average rating, 4 reviews

Lakefront Sunset Retreat with SPA

Experience the best of Southwest Florida living in this beautifully renovated 3-bedroom, 2-bath lakefront retreat in Port Charlotte. Designed for comfort and relaxation, the home features a bright open-concept layout, modern coastal finishes, and serene water views throughout. The fully equipped kitchen with stainless steel appliances and quartz countertops flows into spacious living and dining areas—perfect for gathering or unwinding. Three queen beds and two bunk beds comfortably sleep up to 1

5 out of 5 average rating, 20 reviews

Family Hot Tub Villa w/ Fire-pit + Outdoor Lounge

Welcome to our bright and family-ready Sarasota home, just 15 minutes from Lido Beach and 2 miles from downtown. With 5 bedrooms, a nursery, 2 TV lounges, and hot tub, there’s room for everyone to relax, play, and reconnect. We are a local Sarasota family who loves hosting guests from around the world. Happy to give you our insider tips on best places to eat and drink, secret beach parking, and where to take the kids to the coolest playground. Public teacher discounts available. Message us!

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.

4.77 out of 5 average rating, 22 reviews

Nottingham Beach Bungalow Near Siesta Key Beach!

Book your stay for Winter / Spring 2026 now! Booking November 26th through 2026! 28+ day stays get 30% discount! This cozy Nottingham Beach Bungalow is in a central location 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 short drive to downtown, 10 min to Siesta Key beach.

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

4.92 out of 5 average rating, 147 reviews

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.

4.97 out of 5 average rating, 29 reviews

The enclosed lanai features a spacious seating area with a mix of wooden and wicker furniture. A coffee table is placed on a patterned rug, while large windows offer tranquil views of the lake and surrounding greenery.

Apartment 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

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/Motorhome in Sarasota

4.99 out of 5 average rating, 87 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

The two-story home is framed by lush greenery, showcasing a combination of wooden and stone exterior. A wrap-around deck is visible on the upper level, while the lower level features large windows and a paved pathway leading to the entrance.

4.87 out of 5 average rating, 30 reviews

Tropical Escape, Sarasota!

Discover Real Florida, UP CLOSE! Unique and tranquil. Enjoy nature & everything Sarasota! • Refreshing breezes: private wrap-around deck • Pets welcome* • Comfortable beds, Towels, Bedding • Fully equipped kitchen • Beach gear, Crib, Bikes • 1st day cont. breakfast • Boat/truck/RV* • Air conditioned, hot water • Special occasions* • EV Charging Station* • Secluded, yet close to Beaches, Parks, Shopping, Dining • Pool & fitness • Sleeps 1-12 • 1400 ft.² * Fees apply

A private heated pool is enclosed within a screened area, featuring clear blue water and retaining walls of light-colored stone. Loungers with blue cushions are positioned nearby, and lush greenery can be seen through the screens, creating a serene and tropical environment.

4.82 out of 5 average rating, 141 reviews

Vacation Paradise Close to Beach! After renovation

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!

5 out of 5 average rating, 9 reviews

Cozy Cottage, FirePit, BBQ, 5 Min Downtown

You’ll love Yesterday’s Sunshine for its vintage Florida charm, calming vibe, and newly renovated comfort. Enjoy two cozy bedrooms, a record player with classic vinyl, a dedicated office space, and a spacious outdoor lounge with BBQ, fire pit, and games. It’s the perfect spot to unwind, slow down, and savor sunny, nostalgic Florida living.

Superhost

4.93 out of 5 average rating, 29 reviews

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

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.

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.