Holiday Rentals in Siesta Key

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Our top choices for Siesta Key holiday rentals

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (349 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is €198
includes taxes & fees
10 Feb - 11 Feb
Tiny House Siesta

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,287 reviews)
"Wonderful stay!"
United States
Victoria
The price is €244
includes taxes & fees
8 Feb - 9 Feb
Tropical Beach Resorts

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (2 reviews)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
The price is €221
includes taxes & fees
18 Feb - 19 Feb
The Mermaid at Tiny House Siesta

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 €434
includes taxes & fees
7 Feb - 8 Feb
Beachy Sarasota Duplex

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
South Village
9.6 out of 10, Exceptional, (44 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
The price is €270
includes taxes & fees
8 Feb - 9 Feb
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

Tiny House Calypso with 1st floor sleeping

Tiny House Calypso with 1st floor sleeping
Sarasota
9.0 out of 10, Wonderful, (9 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
The price is €227
includes taxes & fees
18 Feb - 19 Feb
Tiny House Calypso with 1st floor sleeping

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,248 reviews)
"Very clean, and staff was extremely nice. "
United States
Maribeth
The price is €209
includes taxes & fees
10 Feb - 11 Feb
Hibiscus Suites - Gateway to Siesta Key

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (91 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is €469
includes taxes & fees
16 Feb - 17 Feb
SeaSpray Resort

Aqua Oasis- Tiny House sleeps 4 & Pet friendly

Aqua Oasis- Tiny House sleeps 4 & Pet friendly
Sarasota
9.0 out of 10, Wonderful, (34 reviews)
"We enjoyed our stay at this property. Highly recommend giving this place a shot. we'll be back for sure if we visit the area."
United States
Jason V.
The price is €207
includes taxes & fees
18 Feb - 19 Feb
Aqua Oasis- Tiny House sleeps 4 & Pet friendly

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!

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!
Siesta Key
9.4 out of 10, Exceptional, (26 reviews)
"Great place close to everything"
United States
Tracey M.
The price is €528
includes taxes & fees
15 Feb - 16 Feb
SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (39 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
The price is €500
includes taxes & fees
16 Feb - 17 Feb
Siesta Heron Suites & Villas

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (194 reviews)
"Very charming place! Great location for the beach and restaurants. Would definitely stay again."
United States
Blaine
The price is €564
includes taxes & fees
16 Feb - 17 Feb
The Inn On Siesta Key

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 €405
includes taxes & fees
9 Feb - 10 Feb
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!
Siesta Key Village
9.0 out of 10, Wonderful, (38 reviews)
"Very nice "
United States
Dan M.
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3

POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3
Sarasota
9.6 out of 10, Exceptional, (44 reviews)
"The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again."
United States
Mel S.
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3

Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS

Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS
Sarasota
9.4 out of 10, Exceptional, (47 reviews)
"This is our second year staying at the villas i had a great time unit was cleaned ,pool was great,wahing machine worked good cant wait till next year"
United States
Edelmiro R.
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS

Tiny House Yellow Lifeguard Stand- pet friendly

Tiny House Yellow Lifeguard Stand- pet friendly
Sarasota
9.6 out of 10, Exceptional, (45 reviews)
"It was absolutely perfect like the photos show. We had a wonderful time. "
United States
Tiffanie D.
The price is €224
includes taxes & fees
7 Feb - 8 Feb
Tiny House Yellow Lifeguard Stand- pet friendly

Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.6 out of 10, Exceptional, (27 reviews)
"It was a great fit for our family and we enjoyed the experience. "
United States
Stephanie H.
The price is €193
includes taxes & fees
16 Feb - 17 Feb
Tiny House Green Lifeguard Stand - sleeps 5

NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS

NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS
South Village
9.4 out of 10, Exceptional, (44 reviews)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS
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, apart-hotels, 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 favorite 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 depends 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 €201 per night. Entering your travel dates in the search wizard you might find 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 Heron Suites & Villas: This highly rated holiday home rental in Siesta Key is located on the waterfront, and has an outdoor pool, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Another good choice for your trip to Siesta Key is Siesta Key Island Rentals.

How many holiday rentals are there in Siesta Key?

With 395 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 Shell Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. You’ll find favourite places to visit such as Lido Beach and St. Armands Circle in the wider area.

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.