Holiday houses in Bird Key

4.92 out of 5 average rating, 515 reviews

Guesthouse in Sarasota

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.

4.95 out of 5 average rating, 367 reviews

Townhouse in Sarasota

Peacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙

You are safe with me!Enhanced cleaning protocol in place- as per Airbnb guidelines. Welcome! Be yourself! A five star stay, guaranteed. You WILL be happy here! Special occasion? My favorite. I like doing special things for special people. Courtyard w/ lounge chairs, tiki bar, pond & cafe seating! Queen bed and a pullout couch with new mattress! A 1/2 m walk to downtown. 1 of 2 upstairs apartments at The Tropical Nut! We aim to please! No-regret-booking! Will consider-if asked-pets of all kinds!

Superhost

Villa in Sarasota

4.89 out of 5 average rating, 205 reviews

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

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!

4.93 out of 5 average rating, 474 reviews

Guesthouse in Sarasota

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!

4.94 out of 5 average rating, 336 reviews

Guest suite in Sarasota

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *Private Studio* Access Non shared Pool. Studio w/private entrance & private patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! Wet Bar, No kitchen, lite meals only! No hotels in my exclusive area! Live like a local!

4.97 out of 5 average rating, 461 reviews

Guesthouse in Sarasota

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

4.97 out of 5 average rating, 146 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.

4.96 out of 5 average rating, 140 reviews

Apartment in Sarasota

Free Early Chk-in, Super Clean, Free Parking,Bikes

Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb property on the main road 1 mile from downtown Sarasota. Discover over 60 enticing amenities, from a secure room safe to a luxurious, indulgent bed. Just a stone's throw away from downtown Sarasota, Lido Beach, and essential amenities like grocery stores and pharmacies, our corner apartment with a dazzling wrap-around patio is your perfect hideaway. Bicycles at your disposal. Book now

4.93 out of 5 average rating, 183 reviews

Sea-esta Cottage- Cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand-new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

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

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Other great holiday rentals in Bird Key

5 out of 5 average rating, 58 reviews

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

CharlieRating, 5 stars6 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.

4.96 out of 5 average rating, 67 reviews

Condo in Sarasota

Hidden gem perfect for 2 just 5 min from Siesta

KaleyRating, 5 stars1 week ago

I had an absolutely wonderful experience staying at this Airbnb! From the moment I arrived, everything was exactly as described actually, even better. The space was spotless, beautifully decorated, and felt cozy yet modern. It was clear that a lot of thought went into making guests feel at home. The host was incredibly responsive and friendly, providing helpful local tips and checking in to make sure everything was going smoothly. The bed was super comfortable, the Wi-Fi was fast, and all the amenities from the kitchen to the bathroom were top notch. The location was also perfect. Quiet and peaceful, but close to great restaurants, cafes, and public transportation. I especially appreciated the personal touches, like fresh coffee, local guidebooks, and a welcome note. I wouldn’t hesitate to stay here again and highly recommend it to anyone visiting the area. A truly 10/10 experience!

5 out of 5 average rating, 14 reviews

Coastal Retreat near Siesta Key Beach and Downtown

ParkerRating, 5 stars1 month ago

Aubrey’s place is amazing! It’s in a great location close to the best attractions Sarasota has to offer, but you’ll find yourself just wanting to stay inside and enjoy this masterfully decorated space. I cannot exaggerate the fact that it feels like you are stepping into a page in an interior design magazine. Aubrey herself was delightful to communicate with. She left us a very sweet welcome note and little gift. Wish she had a bnb in every town we visit!

5 out of 5 average rating, 8 reviews

Condo in Sarasota

Deluxe 2/2 Pool View, terraces, Top Floor

PaulRating, 5 stars2 months ago

Stayed for the month and didn’t want to leave! Great location, very clean and beautifully decorated! Clara was very responsive, to the point where she went out of her way to find extra, personal beach chairs when we needed them! I can’t say enough positive comments about our experience.

5 out of 5 average rating, 72 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

MarkRating, 5 stars1 week ago

We had a great time there. Lisa was available all the time. House and grounds were great. Instructions were clear and easy. Hope is available next time.

4.92 out of 5 average rating, 74 reviews

Downtown Sarasota | Casa de Zara

BridgetRating, 5 stars2 weeks ago

Casa de Zara is a beautiful and aesthetic property with great amenities and great local finds! The host, Faith, was extremely friendly and responsive. We felt extremely welcomed and at comfortable. The property excelled our expectations and we hope to stay here again!

4.96 out of 5 average rating, 26 reviews

Apartment in Sarasota

Pied-a-Terre

ThadRating, 5 stars2 weeks ago

Great little place walking distance from the botanical gardens and an easy drive to the beaches. Jennifer was very responsive and helpful. We’d gladly stay again!