Holiday rentals in Sarasota County

4.93 out of 5 average rating, 514 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, 197 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, 158 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, 275 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.

Superhost

Flat in Sarasota

4.87 out of 5 average rating, 115 reviews

Cozy Updated Studio Apt-Centrally Located!

Welcome to your exclusive retreat at Foxtail Palm! A meticulously curated haven designed to exceed your expectations. Situated in the heart of Pinecraft, Central Sarasota's esteemed enclave, this quaint abode offers tranquility amidst a backdrop of charming ice cream parlors, gift shops, and vibrant local markets. Benefit from the convenience of one complimentary parking space and unrestricted access to a washer and dryer, ensuring a seamless and stress-free experience throughout your stay.

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!

4.94 out of 5 average rating, 289 reviews

Lovely Guest Studio • 6 Miles to Siesta Key Beach

Welcome to your peaceful retreat.Unplug and relax in this bright, cozy studio just minutes from everything Sarasota has to offer. Whether you’re here for business or leisure, this serene space is designed to help you feel calm, refreshed, and right at home. Comfortable queen-sized bed , Kitchenette with fridge, microwave, and essentials, Full private bathroom and Private entrance, 100 ft from the main house Prime location near restaurants, shops, beaches & downtown quiet enough to relax.

4.97 out of 5 average rating, 144 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.

4.9 out of 5 average rating, 662 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

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Bungalows

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

4.89 out of 5 average rating, 53 reviews

Guest suite in Sarasota

Adorable studio near downtown Sarasota

StephanieRating, 5 stars2 weeks ago

Dorina was an amazing host. She was responsive, helpful, accommodating, and the place looked just as described online. There were additional amenities that really improved our trip, including a cooler, beach chairs, umbrella, etc. This property was a great deal too. Thank you Dorina!

4.92 out of 5 average rating, 12 reviews

Coastal Calm - 3BD/2BA Heated Pool Near Beaches

TeairaRating, 5 stars2 weeks ago

Beautiful home and location. Felt like home, spacious living, lovely neighbors and close to the beach.

4.95 out of 5 average rating, 371 reviews

Guest suite in Sarasota

Mid-Century Suite w/ Private Entrance

PierfrancescoRating, 5 stars4 days ago

The apartment was very cute and really well equipped. A very nice touch was the espresso in the morning. Strongly recommended!

5 out of 5 average rating, 28 reviews

Private Guest Cottage on 5 acres

NickRating, 5 stars1 week 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.

Superhost

Flat in Sarasota

4.97 out of 5 average rating, 68 reviews

Prime Sarasota Location, Modern&Clean Efficiency

GabrielRating, 5 stars9 months ago

I stayed in one of Sharon’s units for 3 mounts during my travel contract and it was the best place I’ve stayed in by far in my travel journey. Super clean, quiet neighborhood and friendly neighbors also close to all the stores. Will definitely stay here again in the future!!

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, 38 reviews

Sarasota Bayside Hideaway

SteveRating, 5 stars1 week ago

We spent two nights at Cole's place. Very clean and quiet and in a nice neighborhood of Sarasota. Close to Ringling art gallery and Asolo Theatre. We would certainly choose Cole's place next time we visit Sarasota.