Holiday rentals in Siesta Key

5 out of 5 average rating, 112 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach Accessories • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

5 out of 5 average rating, 190 reviews

Flat in Sarasota

Modern Luxury Apartment in a House Near Siesta

Large modern construction 950 square foot 1 bedroom apartment. Beautifully furnished, efficient apartment attached to the side of the main house. This unit has a private entrance with bright, modern interior and high ceilings. The apartment offers 1 King bed. The full bathroom has a large shower. A Washer and dryer located inside the apartment. Nestled on a quiet street with easy access to Siesta key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key. Great location!

4.92 out of 5 average rating, 517 reviews

Guest house 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.

4.91 out of 5 average rating, 111 reviews

Guest house in Sarasota

Super Clean Cozy and Quaint steps from the beach

The best of all worlds, cleanliness and steps from the beach. Avoid the crowds at the public beach in this beautiful private beach with lounge chairs already at the beach for your convenience. Literally yards from the beach, exit the ground floor condo and walk 100 yards to the gate to the private beach. Only 2 miles from the village, with an easy close by trolley stop just outside the complex. Beach cart, umbrella, cooler, beach toys and towels provided for your convenience! Look no further.

4.93 out of 5 average rating, 111 reviews

NO Stairs, beachfront & short walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

4.99 out of 5 average rating, 179 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!

5 out of 5 average rating, 204 reviews

Guest house in Sarasota

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

4.88 out of 5 average rating, 103 reviews

[escape to paradise] siesta key beach getaway

Walk to siesta beach from this stylish village house. Perfect for couples & group trips. The home is in a central location on Siesta key. Walking distance to Siesta Key village and beach access 7 (1/2 mile). Enjoy the oversized private patio and with garden views or hop on a bike to siesta beach in less than 5 minutes. Both Siesta Key village and Beach access 7 are less than 1/2 mile from the home. Bikes available onsite ($40 per bike per stay) 1 pet is permitted - $90 per stay

4.89 out of 5 average rating, 221 reviews

Tiny home in Sarasota

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

4.92 out of 5 average rating, 155 reviews

Guest suite in Sarasota

Sweet, pet friendly Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

Guest suite in Siesta Key

4.92 out of 5 average rating, 173 reviews

Cozy Studio - 5 min walk to #1 Siesta Key Beach!

Recently renovated and updated! Adorable studio just steps from Siesta Key Village, and a 5 minute walk to the beach. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**

4.93 out of 5 average rating, 183 reviews

Home in Pinecraft

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.

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Popular amenities for Siesta Key holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Siesta Key

4.97 out of 5 average rating, 68 reviews

Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

GabriellaRating, 5 stars1 week ago

This Airbnb exceeded every expectation! The property was beautiful, spotless, and incredibly well-maintained. The pool was a highlight—clean, peaceful, and the perfect spot to relax every day. The host was friendly, responsive, and made sure we had everything we needed for a comfortable stay.

4.77 out of 5 average rating, 512 reviews

Beachfront Getaway in Siesta Key

AdairRating, 5 stars2 weeks ago

Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!

4.99 out of 5 average rating, 79 reviews

Relax in a Private Tropical Retreat on Siesta Key!

SteveRating, 5 stars1 week ago

myself with my Partner Paula, daughter Sammy and her boyfriend Tom stayed at Jonathan's wonderful house for 2 weeks, starting May 25th 2025. We were all delighted with the house and fully equipped with all our needs. We made use of the communal pool and found those that lived in the community very helpful and friendly. We made use of the Breeze bus that was great for going to the village. I made contact with Jonathan a few times regarding minor things and he responded very quickly.

5 out of 5 average rating, 27 reviews

Flat in Siesta Key

Good Vibrations - stay ON the beach in Siesta Key!

MollyRating, 5 stars1 week ago

Location was excellent, property was clean and as described. Free trolley service right on the corner made traveling to the Village easy. The view of the beach was beautiful and the shower had ample pressure and hot water for the 5 of us. Only thing it was lacking was enough towels and cleaning supplies to keep kitchen area cleaned up after meals. Will. Definitely return in the future!

5 out of 5 average rating, 4 reviews

Spacious 2BR 2nd floor Siesta Key condo - GBB 1274

AminaRating, 5 stars5 months ago

If you are looking for place look no further. It is close to everything and the place is beautiful inside and out. The host were great at keeping me informed via text. I can’t wait to come back in the future.

4.91 out of 5 average rating, 11 reviews

Let's go to the beach and play!

JessicaRating, 5 stars1 week ago

The home was exactly as pictured and perfect for our family, the kids especially enjoyed the pool. Jonathan was very easy to get in touch with. Would definitely stay here again!

4.99 out of 5 average rating, 68 reviews

Home in Sarasota

Fruit /Botanical Garden Estate 2 ml to downtown EV

JessRating, 5 stars2 weeks ago

We cannot say enough great things about this house! The pool and hot tub were our favorite place to be! We watched movies every night from the pool! Plenty of space for all 9 of us. The backyard is so gorgeous you do not even want to leave. So many beautiful tropical plants! We were able to grab some delicious mangos! Everyone raved about the beds, they are so comfortable. Plenty of pool towels available which is a help with 4 teenagers! Shuffleboard was a family favorite and there were plenty of T.V. options for the rainy days. Even the neighborhood peacocks were a big hit. There is a beautiful white one that visited every day! We would recommend this home to anyone, and we cannot wait to come back next year! You won't regret booking this place for your family vacation!