Holiday rentals in Sarasota County

4.92 out of 5 average rating, 515 reviews

La Casetta: "the little house" near to the beaches

La Casetta means, in Italian, little house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.

4.86 out of 5 average rating, 198 reviews

Flat in Sarasota

Updated Old Florida Studio Getaway in Central SRQ

This apt is a breath of fresh air- you'll feel it when you enter and immediately feel calm and at peace. Sparkling clean & spacious with a king-sized, comfortable bed, a full bathroom and kitchenette, & special old Florida style decor gives you the sense of southern hospitality that you're looking for. Central to much of Sarasota, you can be from here to the island of Siesta Key in less than 10 minutes! Whether you're here for business or pleasure, this sweet studio is sure to be a highlight.

4.99 out of 5 average rating, 178 reviews

Guest suite in Sarasota

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!

4.96 out of 5 average rating, 159 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

4.98 out of 5 average rating, 104 reviews

Apartment in Sarasota

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

4.97 out of 5 average rating, 276 reviews

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

4.92 out of 5 average rating, 179 reviews

Cozy Guesthouse in central Sarasota!

This cozy independent guesthouse is perfect for all ocations from a few business day stay to a vacacion getaway. Near to siesta key beach! Enjoy a private room with a comfortable bed, a bathroom with a great shower and hot water, plus a cozy bar-style area perfect for preparing snacks and coffee. You’ll also have access to a small patio where you can unwind, and we provide beach essentials. Perfect for travelers seeking comfort and peace, and a well-equipped space. We’d love to host you!

4.93 out of 5 average rating, 473 reviews

Clean and Modern Sarasota Studio

Our studio is private, comfortable, stylish, & efficient. Whether you are coming for business or leisure, we are sure you will have everything you need. Our home is newer (built in 2020) and we designed this space specifically with Airbnb guests in mind. Our neighborhood is central to almost all of Sarasota! We were born and raised here, and in our opinion this area is central to everything! Whether you are headed to Siesta, Myakka State Park, or UTC mall, you won't be driving for long!

4.97 out of 5 average rating, 145 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Newly renovated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high speed WIFI. Grab the beach chairs and umbrella to enjoy Lido Key or Siesta Key Beaches both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the backyard. Several golf courses near-by or catch Orioles spring training at Ed Smith stadium within walking distance.

4.94 out of 5 average rating, 127 reviews

Cottage in Sarasota

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

4.91 out of 5 average rating, 251 reviews

Cozy Getaway Home in Sarasota Near Beaches & More!

Escape to our peaceful home in Sarasota. Conveniently situated near our famous beaches, UTC, Benderson Park, downtown, and only within a mile of grocery stores and other shops. Enjoy outdoor moments on the patio and spacious yard. Modern amenities include high-speed internet, smart TVs, and a well-equipped updated kitchen and workspace. Washer/dryer on-site as well. Your gateway to relaxation and Sarasota's charm awaits! Please reach out if you have any further questions.

4.9 out of 5 average rating, 664 reviews

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

Holiday rentals for every style

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Flats

Convenient locations with everyday essentials

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Intimate homes, inviting architecture

Popular amenities for Sarasota County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sarasota County

5 out of 5 average rating, 57 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

CharlieRating, 5 stars3 days ago

My wife and I had a great time at this stay. Lots to do at the house along with great beaches and restaurants within a 15-20 minute drive. The house was clean and had everything that you might need. We were able to drive to Disney in just over an hour and a half which provided a different experience to go along with the daily beach/pool trips. Cool AC inside to combat the humid 88 degree weather in June 2025.

Superhost

Flat in Sarasota

4.64 out of 5 average rating, 85 reviews

Condo Dahlia near Siesta Key Beach, Sarasota

ElizabethRating, 5 stars1 week ago

Alexandra is a wonderful host. She is very responsive and helpful. Her place is just as described, very convenient with the added bonus of parking directly at the entrance to the condo. The mattress is excellent!

4.95 out of 5 average rating, 373 reviews

Guest suite in Sarasota

Mid-Century Suite w/ Private Entrance

Terrence EdwardRating, 5 stars4 days ago

Beautiful, private and pristine. Lovely little spot in the corner of quality. Great place for the price Megan's space had more amenities than a hotel room including a private outside shower as well as a Washer and Dryer. If you want a nice quiet getaway this location is highly recommended. Knowing that the beach is a car ride away what else could you ask for? Every time I reached out to the host she responded in a timely fashion. Very clean and cozy.

5 out of 5 average rating, 28 reviews

Private Guest Cottage on 5 acres

NickRating, 5 stars2 weeks ago

This place is just what my wife and I needed. The location was quiet and peaceful: in the country yet minutes from town. The house was clean and spacious. The hosts were personable, friendly, and responsive. Their dogs are sweet. The hosts legitimately made you feel like you were at home or visiting a family member's guest house. Would stay again.

5 out of 5 average rating, 23 reviews

Sarasota Tropical Place in the Heart of the Gulf!

KevinRating, 5 stars1 month ago

We had an amazing time at Agnes's home ! The house was spotless when we arrived—super clean, well-maintained, and clearly cared for with pride. It had everything we needed for a comfortable stay, and the layout made it feel spacious and welcoming. But what really made it stand out was the yard—absolutely beautiful! Plenty of room to relax, play, and enjoy the Florida sunshine. Our dog loved it and so did we. It’s not always easy to find a place that makes both humans and pups equally happy, but this one totally nailed it. If you're looking for a peaceful, pet-friendly getaway with great outdoor space and a sparkling-clean interior, this is the one. We’d definitely stay here again!

5 out of 5 average rating, 66 reviews

Siesta Key Fully-Renovated Unit 5 min to the beach

KadieRating, 5 stars1 week ago

Amazing host! Super communicative and friendly. I would definitely book again in the future!!

4.92 out of 5 average rating, 39 reviews

Sarasota Bayside Hideaway

CameronRating, 5 stars1 day ago

This place was perfect for what we needed. We needed a little space to just be able to pop in and out of for the weekend. Getting in and out was very easy! It was clean, super cute and we felt very comfortable there.