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Our top choices for Siesta Key holiday rentals

[Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.8 out of 10, Exceptional, (13 reviews)
"Great location and accommodation. "
United States
ESTELEN
The price is £244
includes taxes & fees
13 May - 14 May
[Sunny in Siesta] king bed + walk to beach

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, (19 reviews)
"Nice clean and a short walk to everything!"
United States
Ralph S.
The price is £243
includes taxes & fees
8 May - 9 May
Beachside villa in Siesta Key | Canal Front | pool

VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals

VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals
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.
The price is £248
includes taxes & fees
7 May - 8 May
VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (119 reviews)
"Amazing staff, and beautiful property. Very nice place to visit and kid friendly."
United States
Ahmad
The price is £248
includes taxes & fees
2 Jun - 3 Jun
SeaSpray Resort

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is £239
includes taxes & fees
11 May - 12 May
[escape to paradise] siesta key beach getaway

Beach Club | Heated Pool Near Beach | Modern Condo | Gated Access to Beach | Sleeps 6

Beach Club | Heated Pool Near Beach | Modern Condo | Gated Access to Beach | Sleeps 6
South Village
9.4 out of 10, Exceptional, (36 reviews)
"We loved that it was close to the beach. plenty of good restaurants nearby"
United States
Jacob C.
Beach Club | Heated Pool Near Beach | Modern Condo | Gated Access to Beach | Sleeps 6

Walk to Siesta Key Beach & Village – Cozy 2BR , 1BA first floor

Walk to Siesta Key Beach & Village – Cozy 2BR , 1BA first floor
Siesta Key Village
9.8 out of 10, Exceptional, (119 reviews)
"Great little bungalow that is close to everything you need without car!! Love this place 3 x staying here"
United States
ryan t.
Walk to Siesta Key Beach & Village – Cozy 2BR , 1BA first floor

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is £290
includes taxes & fees
10 May - 11 May
Siesta Key Island Rentals

Tiny Coral Oasis- beachy tiny house for your getaway

Tiny Coral Oasis- beachy tiny house for your getaway
Sarasota
9.0 out of 10, Wonderful, (20 reviews)
"Cute tiny house Clean and comfortable Had a great time"
United States
DeAnna T.
The price is £151
includes taxes & fees
13 May - 14 May
Tiny Coral Oasis- beachy tiny house for your getaway

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,247 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
The price is £186
includes taxes & fees
10 May - 11 May
Captiva Beach Resort

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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)
"Absolutely beautiful place. Very clean, easy check-in, wonderful location"
United States
Christine
The price is £380
includes taxes & fees
12 May - 13 May
Lulu's Key House Kemp Ridley 1/1 Downstairs

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (42 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is £238
includes taxes & fees
11 May - 12 May
Siesta Heron Suites & Villas

Mimosa | Located in Siesta Key Village w/ Heated Pool and Just Steps to Beach!

Mimosa | Located in Siesta Key Village w/ Heated Pool and Just Steps to Beach!
Siesta Key Village
8.8 out of 10, Excellent, (15 reviews)
"Nice place! Would stay here again. Perfect location. "
United States
Laura
The price is £599
includes taxes & fees
12 May - 13 May
Mimosa | Located in Siesta Key Village w/ Heated Pool and Just Steps to Beach!

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,470 reviews)
"Great place to stay, beach 2 minute walk."
United States
Joseph
The price is £174
includes taxes & fees
25 May - 26 May
Tropical Beach Resorts

Aqua Oasis- Tiny House sleeps 4 & Pet friendly

Aqua Oasis- Tiny House sleeps 4 & Pet friendly
Sarasota
9.0 out of 10, Wonderful, (36 reviews)
"Perfect for a quick stay in Sarasota! Convenient location, clean, and cozy!"
United States
Joe N.
The price is £147
includes taxes & fees
11 May - 12 May
Aqua Oasis- Tiny House sleeps 4 & Pet friendly

Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (103 reviews)
"Property is amazing spot, did stay a year before and was amazing this time furniture had damage and ac was not cooling perfect."
United States
Ubaldo M.
The price is £272
includes taxes & fees
20 May - 21 May
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (72 reviews)
"Perfect little place for a long weekend away. Conveniently located by everything "
United States
Emily D.
The price is £344
includes taxes & fees
9 May - 10 May
Siesta Cooler: Only Minutes Walk to Siesta Beach!

2 Bedroom 2 Bath home near Siesta Key Beach

2 Bedroom 2 Bath home near Siesta Key Beach
Sarasota
8.6 out of 10, Excellent, (39 reviews)
"House was conveniently located. "
United States
CHRISTINE V.
The price is £175
includes taxes & fees
11 May - 12 May
2 Bedroom 2 Bath home near Siesta Key Beach

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is £225
includes taxes & fees
20 May - 21 May
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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 £141 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 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 399 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. While here, Crescent Beach and Siesta Key Marina 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.