A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

Siesta Key Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Siesta Key holiday rentals

2 bedrooms, iron/ironing board, WiFi, bed sheets

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 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 HK$800
HK$2,521 total
includes taxes & fees
5 Jul - 6 Jul
[escape to paradise] siesta key beach getaway
Beach

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (34 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is HK$961
HK$2,524 total
includes taxes & fees
5 Jul - 6 Jul
[Beach Elements] pool view withprivate beach access
Front of property – evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,273 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is HK$1,293
HK$1,594 total
includes taxes & fees
9 Jul - 10 Jul
Captiva Beach Resort
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, (31 reviews)
"Couldn’t see beach but a short walk to it. "
United States
Tim G.
The price is HK$784
HK$3,758 total
includes taxes & fees
7 Jul - 8 Jul
SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!
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, (47 reviews)
"Great place to stay"
United States
Brad S.
Siesta Key Village-Suite #1: A block to the Beach!
Beach nearby, sun-loungers, beach towels, snorkelling

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
9.6 out of 10, Exceptional, (16 reviews)
"the place was great and the host was very responsive to out requests."
United States
David R.
Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock
Outdoor dining

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 HK$808
HK$1,528 total
includes taxes & fees
12 Jul - 13 Jul
Tiny Coral Oasis- beachy tiny house for your getaway
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, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is HK$3,509
HK$4,400 total
includes taxes & fees
10 Jul - 11 Jul
The Inn On Siesta Key
Outdoor dining

Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is HK$1,209
HK$3,346 total
includes taxes & fees
8 Jul - 9 Jul
Dolphin Villa - Pool - Steps to Siesta Key Village
Beach nearby, beach umbrellas

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (87 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
The price is HK$1,357
HK$2,833 total
includes taxes & fees
6 Jul - 7 Jul
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
Outdoor dining

Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Everglades Villa • Sleeps 8 • Walk to Siesta Beach
Siesta Key Village
9.0 out of 10, Wonderful, (14 reviews)
"We enjoyed our stay at Everglades Villa. The location was the best feature as we were able to walk to Siesta Key Village and the beach. "
United States
Lisa S.
The price is HK$1,795
HK$4,336 total
includes taxes & fees
7 Jul - 8 Jul
Everglades Villa • Sleeps 8 • Walk to Siesta Beach
Living area

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is HK$1,041
HK$2,753 total
includes taxes & fees
6 Jul - 7 Jul
Siesta Heron Suites & Villas
Terrace/patio

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, (40 reviews)
"Great little place -perfect for a few days in siesta "
United States
Linda K.
The price is HK$933
HK$2,405 total
includes taxes & fees
5 Jul - 6 Jul
2 Bedroom 2 Bath home near Siesta Key Beach
Beach nearby, beach umbrellas

Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (118 reviews)
"Convenient location - close to beach. Umbrella & beach chairs in closet came in handy. "
United States
Mary
The price is HK$1,278
HK$2,692 total
includes taxes & fees
5 Jul - 6 Jul
Bright & Beachy–Beach Club Siesta Key 100A by RVA
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, (43 reviews)
"Great location Perfect for 2 people Parking is tight needs to be in bold print prior to booking "
United States
Allison K.
Siesta Key Village-Suite #4: A block to the Beach!
Property grounds

Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village
Siesta Key Village
8.4 out of 10, Very good, (13 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is HK$1,127
HK$3,513 total
includes taxes & fees
8 Jul - 9 Jul
Island Villa | Cozy Beach Retreat | Walk to Village
Beach nearby

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, (37 reviews)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is HK$2,037
HK$3,869 total
includes taxes & fees
7 Jul - 8 Jul
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Property grounds

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, (164 reviews)
"It was a great place. And just about a 5 min walk to the beach. "
United States
DESIREE
The price is HK$1,490
HK$2,519 total
includes taxes & fees
5 Jul - 6 Jul
Studio Retreat Across the Street from Beautiful Siesta Key Beach
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,620 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is HK$1,327
HK$1,703 total
includes taxes & fees
2 Aug - 3 Aug
Tropical Beach Resorts
TV, offices

Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (32 reviews)
"Highly recommended for adventure guests. I suggest having a spot to dry towels and clothes. Thank you. "
United States
Abdias O.
Tiny House Green Lifeguard Stand - sleeps 5
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

SeaSpray Resort

SeaSpray Resort

10/10 Excellent
"Excelente people"
Fabián 2-night trip
Posted 2 hours ago
SeaSpray Resort

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:

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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 3 bed 2 Bath, heated pool, walk to beach and village.

How many holiday rentals are there in Siesta Key?

With 424 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 Siesta Key Beach Playground 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.