Siesta Key Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Siesta Key holiday rentals

Living area

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 HK$614
HK$1,643 total
includes taxes & fees
5 Mar - 6 Mar
Tiny House Siesta
2 bedrooms, WiFi, bed sheets

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 HK$938
HK$1,658 total
includes taxes & fees
16 Feb - 17 Feb
Tiny House Calypso with 1st floor sleeping
In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (93 reviews)
"Clean, comfortable, well stocked. Staff made our stay a breeze. Would definitely come back again."
Canada
Robert
The price is HK$3,822
HK$4,319 total
includes taxes & fees
18 Feb - 19 Feb
SeaSpray Resort
Interior

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 HK$969
HK$1,693 total
includes taxes & fees
19 Feb - 20 Feb
The Mermaid at Tiny House Siesta
Private kitchen

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 HK$2,005
HK$4,728 total
includes taxes & fees
15 Feb - 16 Feb
Beachy Sarasota Duplex
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,299 reviews)
"Wonderful stay!"
United States
Victoria
The price is HK$2,295
HK$2,796 total
includes taxes & fees
18 Feb - 19 Feb
Tropical Beach Resorts
Beach nearby, sun-loungers, beach towels

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
The price is HK$1,174
HK$2,937 total
includes taxes & fees
25 Feb - 26 Feb
Siesta Key Village-Suite #1: A block to the Beach!
Beach nearby, white sand, beach umbrellas, beach towels

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 HK$3,112
HK$3,949 total
includes taxes & fees
16 Feb - 17 Feb
The Inn On Siesta Key
Exterior

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,198 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 HK$2,083
HK$2,486 total
includes taxes & fees
18 Feb - 19 Feb
Captiva Beach Resort
Exterior detail

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 HK$938
HK$1,689 total
includes taxes & fees
18 Feb - 19 Feb
Aqua Oasis- Tiny House sleeps 4 & Pet friendly
On 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)
"Close to the beach and so convenient to local food and shops. The rental was nicely decorated and the terrace area was a treat. Definitely would stay here again!!"
United States
Sheila C.
The price is HK$1,555
HK$4,686 total
includes taxes & fees
15 Feb - 16 Feb
SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!
TV, offices

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 HK$1,423
HK$2,261 total
includes taxes & fees
24 Feb - 25 Feb
Tiny House Green Lifeguard Stand - sleeps 5
Private kitchen

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 HK$3,143
HK$5,053 total
includes taxes & fees
24 Feb - 25 Feb
Siesta Key Island Rentals
Living area

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 HK$2,319
HK$5,438 total
includes taxes & fees
13 Feb - 14 Feb
Siesta Heron Suites & Villas
Fridge, microwave, stovetop, coffee/tea maker

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 HK$1,110
HK$1,852 total
includes taxes & fees
23 Feb - 24 Feb
Red Lifeguard Stand - pet freindly
TV

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.
The price is HK$1,946
HK$3,292 total
includes taxes & fees
16 Feb - 17 Feb
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,249 reviews)
"Very clean, and staff was extremely nice. "
United States
Maribeth
The price is HK$2,083
HK$2,354 total
includes taxes & fees
15 Feb - 16 Feb
Hibiscus Suites - Gateway to Siesta Key
Property grounds

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.
The price is HK$1,174
HK$2,866 total
includes taxes & fees
15 Feb - 16 Feb
Siesta Key Village-Suite #4: A block to the Beach!
Outdoor dining

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Siesta Key Village
9.0 out of 10, Wonderful, (13 reviews)
"Great location, clean, good communication. "
United States
Alexandra P.
The price is HK$3,317
HK$6,251 total
includes taxes & fees
12 Mar - 13 Mar
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
TV, offices

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.
Tiny House Yellow Lifeguard Stand- pet friendly
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

The Capri at Siesta

The Capri at Siesta

10/10 Excellent
"Couldn't have asked for a better stay. Room was very well priced. It was very clean, quiet, the amenities were really nice, it was really close to the beach, and the owner was extremely friendly, welcoming, and helpful. I would 100% stay here again. Highly recommend."
Austyn 2-night trip
Posted 3 days ago
The Capri at Siesta

Find out more about Siesta Key

Search for holiday rentals in Siesta Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Siesta Key using one of the methods below:

  • View our selection of featured holiday rentals in Siesta Key
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  • Enter your travel dates to view the best deals on holiday rentals in Siesta Key while they last

Look no further and take a look at our great range of rental properties in Siesta Key!

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.