Holiday Homes in Siesta Key

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Featured Holiday Homes in Siesta Key

Our top choices for Siesta Key holiday homes

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas

The Mermaid at Tiny House Siesta

2.0 star property
10.0 out of 10, Exceptional, (2)
"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."
The price is AU$286
includes taxes & fees
22 Aug - 23 Aug
The Mermaid at Tiny House Siesta

Tiny House Yellow Lifeguard Stand- pet friendly

9.6 out of 10, Exceptional, (43)
"We enjoyed the stay and it worked well. "
The price is AU$305
includes taxes & fees
22 Aug - 23 Aug
Tiny House Yellow Lifeguard Stand- pet friendly

RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette

9.6 out of 10, Exceptional, (35)
"The unit is very nice with everything for a great comfortable stay.. the water view and onsite restaurants are a bonus "
The price is AU$387
includes taxes & fees
3 Sept - 4 Sept
RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette

Experience Modern Comfort Near Sarasota's Attractions

The price is AU$212
includes taxes & fees
3 Sept - 4 Sept
Experience Modern Comfort Near Sarasota's Attractions

POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

9.6 out of 10, Exceptional, (32)
"We enjoyed our stay. Close to the beach. enjoyed the pool.Kitchen was perfect we were able to make breakfast and dinner."
The price is AU$448
includes taxes & fees
24 Aug - 25 Aug
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

Heated Pool, Strong WI-FI, TV, Tiki Bar & Grill, Boat and Kayak Rentals

8.6 out of 10, Excellent, (9)
"I was looking for a nice place close to the airport and my events, and that's what I found."
The price is AU$287
includes taxes & fees
3 Sept - 4 Sept
Heated Pool, Strong WI-FI, TV, Tiki Bar & Grill, Boat and Kayak Rentals

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

9.4 out of 10, Exceptional, (40)
"Just steps to the beach restaurants and shopping"
The price is AU$405
includes taxes & fees
25 Aug - 26 Aug
NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS

Sea Turtle- Full Sized living at Tiny House Siesta

9.6 out of 10, Exceptional, (14)
"The tiny house was one of my favorite places I’ve had the pleasure of staying in! The house and property gave off a very “beachy” vibe. The communication with property manager was amazing!! If you have the chance to stay here…You won’t be disappointed!!! "
The price is AU$282
includes taxes & fees
2 Sept - 3 Sept
Sea Turtle- Full Sized living at Tiny House Siesta

[escape to paradise] siesta key beach getaway

10.0 out of 10, Exceptional, (21)
"Clean and great location! Would stay again! "
The price is AU$483
includes taxes & fees
3 Sept - 4 Sept
[escape to paradise] siesta key beach getaway

POOL VIEW V5 Luxury King Bedroom Siesta Key Walk to beach DAILY SPECIALS

9.8 out of 10, Exceptional, (110)
"Very comfortable beds and linens, extremely clean room and beds. "
The price is AU$329
includes taxes & fees
25 Aug - 26 Aug
POOL VIEW V5 Luxury King Bedroom Siesta Key Walk to beach DAILY SPECIALS

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

9.2 out of 10, Wonderful, (33)
"The property was very clean and in a great location. We had no problems with our stay and had a nice time."
The price is AU$717
includes taxes & fees
3 Sept - 4 Sept
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

[Ocean Oasis] guest house on siesta key

The price is AU$433
includes taxes & fees
3 Sept - 4 Sept
[Ocean Oasis] guest house on siesta key

"Safe & Clean" Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -

9.6 out of 10, Exceptional, (39)
"The location of this property was great, the property was very clean, and Virginia was quickly available for all of our needs."
The price is AU$756
includes taxes & fees
3 Sept - 4 Sept
"Safe & Clean" Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -

Walk to the Beach and Village- Fiji Villa

10.0 out of 10, Exceptional, (13)
"Great location 💯 easy walk to the beach & great restaurants & pet friendly 😺"
The price is AU$653
includes taxes & fees
24 Aug - 25 Aug
Walk to the Beach and Village- Fiji Villa

Oceanfront home w/sunset views of Sarasota Bay

9.8 out of 10, Exceptional, (118)
"Perfect 2 week vacation in this house, second time staying here."
Oceanfront home w/sunset views of Sarasota Bay

Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

10.0 out of 10, Exceptional, (21)
"Near beach and town."
The price is AU$1,484
includes taxes & fees
3 Sept - 4 Sept
Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Close to Sarasota Beach/Pet Friendly

9.2 out of 10, Wonderful, (5)
"Pictures represent the place very well. The cons..need of renovation inside, no pool. The pros…very clean, great communication, great location, quiet at night, stocked well. We felt being able to walk to everything was a huge draw. The price reflects the older inside so don’t be afraid to stay here! We would definitely stay again!"
Close to Sarasota Beach/Pet Friendly

[Tropical] guesthouse retreat on Siesta Key

[Tropical] guesthouse retreat on Siesta Key

Condo with Private Beach Access, Great Shared Amenities - Private Beach House

9.0 out of 10, Wonderful, (43)
"This rental was in a great area with access to the free trolley. The beach was amazing! I would definitely stay here again."
Condo with Private Beach Access, Great Shared Amenities - Private Beach House
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