Siesta Key Holiday Rentals, Florida: Private House Rentals

Our top choices for Siesta Key hotels

Tropical Beach Resorts

South Village

crystal

6.226.378 ₫ total

includes taxes & fees

25 May - 26 May

Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

Gerard

3.881.393 ₫ total

includes taxes & fees

13 May - 14 May

Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

Sarasota

Lynn

4.409.490 ₫ total

includes taxes & fees

30 Apr - 1 May

Beach Club Modern Condo C Bldg

South Village

14.606.515 ₫ total

includes taxes & fees

4 May - 5 May

Siesta Key Palms Resort

Sarasota

Ben

4.824.574 ₫ total

includes taxes & fees

11 May - 12 May

Captiva Beach Resort

South Village

Angela

7.069.744 ₫ total

includes taxes & fees

26 May - 27 May

Tropical Breeze Resort

Siesta Key Village

Steven Howard

7.297.947 ₫ total

includes taxes & fees

12 May - 13 May

Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

Sarasota

Shelly

6.148.133 ₫ total

includes taxes & fees

3 May - 4 May

Siesta Key Beachside Villas

Siesta Key Village

Eduardo Guerrero

7.819.723 ₫ total

includes taxes & fees

25 May - 26 May

On the beach, white sand, sun-loungers, beach umbrellas

Azul Resort Siesta Key

South Village

Antonio

6.059.219 ₫ total

includes taxes & fees

3 May - 4 May

Siesta Key Beach Resort and Suites

Siesta Key Village

Megan

6.825.200 ₫ total

includes taxes & fees

26 May - 27 May

Siesta Heron 7

Siesta Key

Beach nearby, white sand, beach umbrellas, beach towels

The Inn On Siesta Key

Siesta Key

Amanda

Minorga Sand Dollar on the Key

Siesta Key Village

14.342.217 ₫ total

includes taxes & fees

20 May - 21 May

Unwind Poolside + Walk to Beach! Sarasota Retreat

South Village

"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "

Eleuterio

14.186.015 ₫ total

includes taxes & fees

17 May - 18 May

Siesta Key Island Rentals

Siesta Key

Alessandra

Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

Siesta Key

Ahmad

8.901.185 ₫ total

includes taxes & fees

27 May - 28 May

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Allie

19.643.340 ₫ total

includes taxes & fees

21 May - 22 May

House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

Siesta Heron Suites & Villas

Siesta Key

Christopher Robert

9.212.668 ₫ total

includes taxes & fees

12 May - 13 May

Outdoor pool, free pool cabanas, pool umbrellas

Turtle Beach Resort

Siesta Key

Michael

7.890.907 ₫ total

includes taxes & fees

30 Apr - 1 May

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Holiday Rentals in Siesta Key

Holiday Home

Siesta Key Island Rentals

Siesta Key

"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."

Holiday Home

Siesta Heron Suites & Villas

Siesta Key

"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"

Cottage

Sarasota Vacation Rental w/ Pool & Game Room!

Sarasota

"The property was perfect for our family. We had enough space for everyone. We enjoyed the pool, game room and the patio to grill. the neighbors were friendly! I would put a rug in front of the pool patio door inside to catch any dirt walking in, and that area can be very slippery with wet feet walking on the tile. Great stay! "

Aparthotel

Hibiscus Suites - Gateway to Siesta Key

Sarasota

"Excellent location, great place to stay! "

Holiday Home

Condo (LuLu's Key House Kemp Ridley 1/1 Down) | Exterior

Lulu's Key House Kemp Ridley 1/1 Downstairs

Siesta Key Village

"Absolutely beautiful place. Very clean, easy check-in, wonderful location"

Condo

Siesta Sands Beach Resort Gulf View

South Village

"Loved to property! Clean and accommodating. Had a beautiful ocean view and could walk right out to the beach. Pool area was clean."

Condo

House of The Sun Siesta Key Crescent Beach

South Village

"The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . "

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Where to stay in Siesta Key

Find the best Siesta Key areas for the activities you enjoy most. Learn more about Siesta Key

Siesta Key Village

This lively beach hub sits adjacent to Siesta Beach, one of America's top-rated shorelines. The compact village streets are lined with open-air restaurants, tiki bars, and colourful beach boutiques. Palm trees sway above outdoor dining patios where sunset cocktails flow freely. Travellers can easily explore the area on foot, enjoying live music that drifts from waterfront venues. The sugar-white sands and crystal-clear Gulf waters are just steps away. Shop for local crafts at the Siesta Key Farmers Market or simply relax in this quintessential beach paradise.

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sunset over the bay, water, sky, red, intense, swirls, clouds, landscape, island, horizon, tropical, Siesta Key, Florida

Bay Island

Bay Island offers a secluded paradise within Siesta Key with direct access to award-winning beaches. This exclusive waterfront community features luxury homes with private docks and stunning views of Sarasota Bay and the Gulf of Mexico. Pristine waters surround this affluent enclave where privacy comes standard. The island serves as a perfect base for exploring nearby attractions. Shell Beach and Lido Beach lie just minutes away by car. Travellers can easily visit Marie Selby Botanical Gardens or browse upscale shops at St. Armands Circle in neighbouring Sarasota.

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South Village

If you're spending some time in South Village, Siesta Key Marina and Crescent Beach are top sights worth seeing.

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Aloha Kai

Aloha Kai offers a peaceful retreat on Siesta Key with direct access to world-renowned white sand beaches. This residential haven features luxury holiday rentals and condominiums set against the stunning backdrop of the Gulf of Mexico. The neighborhood's contemporary coastal architecture blends perfectly with manicured tropical landscapes. Walk along waterfront paths with views of both the Gulf and intracoastal waterways. The crystal-clear waters are ideal for swimming year-round. While quiet within its boundaries, Siesta Key Beach, Crescent Beach, and Siesta Key Village are just minutes away.

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Bailey Hall

Bailey Hall might not have many top sights, but Siesta Key Beach and Lido Beach are two attractions nearby that you can check out.

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Stay near popular Siesta Key attractions

Siesta Key Beach

4.8/5 (4,113 reviews)

Siesta Beach captivates with its unique quartz sand that stays cool even on hot days. Sink your toes into the powdery white shoreline while gazing at the clear turquoise waters that make this beach a favourite.

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Learn more about Siesta Key

The powdery white sand of Siesta Beach feels cool underfoot even on the hottest summer days. Rent a paddleboard at sunset to glide through the calm Gulf waters and spot dolphins arcing alongside you.

See all hotels in Siesta Key

Top Siesta Key Hotel Reviews

Tropical Breeze Resort

10/10 Excellent

"Staff were wonderful. Room was beautiful. You can be the location"

Tropical Beach Resorts

8/10 Good

"The new pool was amazing. The property was beautiful and well maintained loved the beach access. Only 1 small detail, I Really wish you had a coffee spot for us early risers. The coffee pot in the room just doesn’t cut it . Ended up driving to the 711. It was an amazing place to stay.🌼🌊🌸"

Siesta Key Beachside Villas

10/10 Excellent

"The parking its perfect,the hotel its sow near to the beach that u can go on foot and can use all the aminities its sow personal i was with my wife and was super relaxing, the place its beautiful this are my second time there because the cleaning in all the way of the word, its super clean i love it, its small but perfect for a getaways "

Azul Resort Siesta Key

10/10 Excellent

"The location is great short walk distance to to beach, stores and restaurants. The room I stayed in didn’t have microwave I stayed for only one night but if I was going to stay longer it will be a down point to me. The room was clean and well maintained. I arrived after the reception was closed but check in was easy I was give my door code after a short phone call. Definitely recommend this property. "

The Ringling Beach House

10/10 Excellent

"I don't know where to start because everything was so great! The staff was professional and very helpful, the room was clean and had all the amenities we could have asked for. Most importantly though, this location is literally a small walk away from the beach which makes it ever more awesome to stay at! It also is away from where all the bars and partying happens on the weekends so it stays relatively quiet on this side. Excellent place for families or couples looking for a quiet but fun vacation!"

More cheap stays in Siesta Key

Hibiscus Suites - Gateway to Siesta Key

1735 Stickney Point Rd Sarasota FL

3.902.203 ₫

4.409.490 ₫ total

30 Apr - 1 May

includes taxes & fees

8.6/10 Excellent! (2,301 reviews)

Frequently asked questions

What's the seasonal weather in Siesta Key?

The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 19°C. Average annual precipitation for Siesta Key is 1126 mm.

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Our top choices for Siesta Key hotels

Tropical Beach Resorts

Spark by Hilton Sarasota Siesta Key Gateway

Hibiscus Suites - Gateway to Siesta Key

Beach Club Modern Condo C Bldg

Siesta Key Palms Resort

Captiva Beach Resort

Tropical Breeze Resort

Tiny House Siesta

Siesta Key Beachside Villas

Azul Resort Siesta Key

Siesta Key Beach Resort and Suites

Siesta Heron 7

The Inn On Siesta Key

Minorga Sand Dollar on the Key

Unwind Poolside + Walk to Beach! Sarasota Retreat

Siesta Key Island Rentals

SeaSpray Resort

The Residences at Siesta Key Beach by Hyatt Vacation Club

Siesta Heron Suites & Villas

Turtle Beach Resort

Holiday Rentals in Siesta Key

Siesta Key Island Rentals

Where to stay in Siesta Key

Siesta Key Village

Bay Island

South Village

Aloha Kai

Bailey Hall

Stay near popular Siesta Key attractions

Siesta Key Beach

Learn more about Siesta Key

Top Siesta Key Hotel Reviews

Tropical Breeze Resort

More cheap stays in Siesta Key

Hibiscus Suites - Gateway to Siesta Key

Frequently asked questions

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