Siesta Key Holiday Rentals

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Our top choices for Siesta Key holiday rentals

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
The price is AU$859
includes taxes & fees
15 Mar - 16 Mar
Beachy Sarasota Duplex

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (26 reviews)
"Clean and comfortable. "
United States
Laney
The price is AU$634
includes taxes & fees
8 Mar - 9 Mar
[escape to paradise] siesta key beach getaway

Tiny House Calypso with 1st floor sleeping

Tiny House Calypso with 1st floor sleeping
Sarasota
9.0 out of 10, Wonderful, (10 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
The price is AU$380
includes taxes & fees
24 Mar - 25 Mar
Tiny House Calypso with 1st floor sleeping

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (178 reviews)
"Wonderful property with an excellent location! Beach access was across the street and the trolley pick-up was at the end of the block. The village was within walking distance as well. The property was very clean and the beds were comfortable. The washer and dryer is located right outside of the unit and beach chairs and a cooler were provided. We look forward to booking this property again in the future! "
United States
Alison B.
The price is AU$748
includes taxes & fees
23 Feb - 24 Feb
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Village-Suite #4: A block to the Beach!

Siesta Key Village-Suite #4: A block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (36 reviews)
"A great location with easy walk to the beach!"
United States
Alan M.
Siesta Key Village-Suite #4: A block to the Beach!

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Siesta Key
9.2 out of 10, Wonderful, (34 reviews)
"We stayed in building 6 which had amazing space and private entrence. The bikes allowed us to ride to the beach every morning. Would recommend. "
United States
lucas c.
The price is AU$796
includes taxes & fees
3 Mar - 4 Mar
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock

Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock
Sarasota
9.4 out of 10, Exceptional, (13 reviews)
"We loved the closeness to the bay, our backyard"
United States
Alec V.
Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock

Red Lifeguard Stand - pet freindly

Red Lifeguard Stand - pet freindly
Sarasota
9.6 out of 10, Exceptional, (25 reviews)
"I really had a great experience the owners was super friendly helpful any question I had to right away response. Cute little spot to experience little Home clean and very good location."
United States
Naomi G.
The price is AU$305
includes taxes & fees
23 Feb - 24 Feb
Red Lifeguard Stand - pet freindly

Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
8.8 out of 10, Excellent, (156 reviews)
"Pristinely clean comfortable and very close to beach with free parking it was a great place to stay! Would recommend!"
United States
Stina
The price is AU$571
includes taxes & fees
22 Feb - 23 Feb
Studio Retreat Across the Street from Beautiful Siesta Key Beach

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (95 reviews)
"Clean, comfortable, well stocked. Staff made our stay a breeze. Would definitely come back again."
Canada
Robert
The price is AU$780
includes taxes & fees
25 Feb - 26 Feb
SeaSpray Resort

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (59 reviews)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is AU$792
includes taxes & fees
24 Feb - 25 Feb
Siesta Key Island Rentals

Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly
Siesta Key Village
9.8 out of 10, Exceptional, (77 reviews)
"Property was beautiful and clean, just as described. Great location close to the beach and the village - could walk everywhere. "
United States
Naomi J.
The price is AU$1,574
includes taxes & fees
23 Feb - 24 Feb
Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (351 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is AU$300
includes taxes & fees
5 Mar - 6 Mar
Tiny House Siesta

Beachside villa in Siesta Key | Canal Front | pool

Beachside villa in Siesta Key | Canal Front | pool
Siesta Key Village
9.8 out of 10, Exceptional, (18 reviews)
"The room was very clean and close to everything. We had to buy toilet paper and Kleenex as there wasn’t enough for the room. Enjoyed our stay"
United States
Kelly F.
The price is AU$929
includes taxes & fees
27 Feb - 28 Feb
Beachside villa in Siesta Key | Canal Front | pool

Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ

Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ
Siesta Key Village
8.8 out of 10, Excellent, (11 reviews)
"My absolute favorite place to stay! Clean, friendly and perfect location to the beach and village."
United States
Tisha P.
The price is AU$1,093
includes taxes & fees
23 Feb - 24 Feb
Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ

Siesta Shores 2Bed/2Bath Heated Pool!

Siesta Shores 2Bed/2Bath Heated Pool!
Sarasota
10.0 out of 10, Exceptional, (2 reviews)
"it checked all the boxes"
United States
Patrick
The price is AU$860
includes taxes & fees
22 Feb - 23 Feb
Siesta Shores 2Bed/2Bath Heated Pool!

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (45 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
Siesta Key Village-Suite #1: A block to the Beach!

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,203 reviews)
"Staff really were accommodating. The location was perfect and the rooms were clean and quiet. We enjoyed the pool and beach."
United States
Glenn
The price is AU$527
includes taxes & fees
23 Feb - 24 Feb
Captiva Beach Resort

Lulu's Key House Kemp Ridley 1/1 Downstairs

Lulu's Key House Kemp Ridley 1/1 Downstairs
3.5 star property
Siesta Key Village
10.0 out of 10, Exceptional, (4 reviews)
"Loved the location! "
United States
Angel J
The price is AU$1,160
includes taxes & fees
4 Mar - 5 Mar
Lulu's Key House Kemp Ridley 1/1 Downstairs

Perfect Location minutes to beach and downtown with heated pool and hot tub

Perfect Location minutes to beach and downtown with heated pool and hot tub
Sarasota
9.8 out of 10, Exceptional, (8 reviews)
"This place was perfect and close to everything!! "
United States
Christina R.
The price is AU$500
includes taxes & fees
23 Feb - 24 Feb
Perfect Location minutes to beach and downtown with heated pool and hot tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Siesta Key Hotel Reviews

Find out more about Siesta Key

Everything you need to know about Siesta Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Siesta Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Siesta Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Siesta Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Siesta Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Siesta Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Siesta Key holiday rentals we have selected for you start as low as AU$332 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Siesta Key rentals

At Expedia, we put the best Siesta Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Siesta Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Siesta Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Siesta Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Siesta Key?

Yes, there are holiday rentals in Siesta Key close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Siesta Key like the popular beaches and live music. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that Siesta Key has to offer?

Siesta Key Island Rentals: This highly rated holiday home rental in Siesta Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Siesta Key is Siesta Heron Suites & Villas.

How many holiday rentals are there in Siesta Key?

With 396 Expedia holiday rentals, you're guaranteed to find just the right place for your Siesta Key stay.

What can I see and do in Siesta Key?

Siesta Key Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. While here, Siesta Key Marina and Point of Rocks are other places worth a visit.

What are holiday rentals like in Siesta Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Siesta Key. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.