Search Holiday Homes in Siesta Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Siesta Key holiday homes

[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 £225
includes taxes & fees
13 May - 14 May
[escape to paradise] siesta key beach getaway

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

Private Beach Access w/shared Pool -Casita East

Private Beach Access w/shared Pool -Casita East
South Village
9.2 out of 10, Wonderful, (5 reviews)
"A beautiful beach cottage that's minutes from a lesser-known but just as beautiful stretch of Siesta Key. We'll be returning for sure :)"
United States
Leigh T.
The price is £452
includes taxes & fees
10 May - 11 May
Private Beach Access w/shared Pool -Casita East

Newly Renovated Beach-Side villa | Pool | Dock

Newly Renovated Beach-Side villa | Pool | Dock
Siesta Key Village
9.2 out of 10, Wonderful, (15 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 £315
includes taxes & fees
11 May - 12 May
Newly Renovated Beach-Side villa | Pool | Dock

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
South Village
8.8 out of 10, Excellent, (5 reviews)
"Very nice. Walking distance to beach and restaurants"
United States
Mark P.
The price is £454
includes taxes & fees
11 May - 12 May
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

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, (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 £349
includes taxes & fees
12 May - 13 May
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

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
Siesta Key Island Rentals

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, (36 reviews)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is £344
includes taxes & fees
10 May - 11 May
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

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
12 May - 13 May
2 Bedroom 2 Bath home near Siesta Key Beach

Pet Friendly home, Close to Sarasota Beach!

Pet Friendly home, Close to Sarasota Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (7 reviews)
"Great communication from host and close to everything!"
United States
stacey m.
The price is £448
includes taxes & fees
13 May - 14 May
Pet Friendly home, Close to Sarasota Beach!

Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ

Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ
Siesta Key Village
9.0 out of 10, Wonderful, (12 reviews)
"Very cute & clean. Great location!"
United States
Nannette
The price is £361
includes taxes & fees
3 Jun - 4 Jun
Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"The inside was very clean, we were very impressed! Being only a few minutes away from the beach, the location was perfect for what we had in mind. Area was surrounded by places to go shop as well. Would definitely stay again!"
United States
Jaret
The price is £155
includes taxes & fees
12 May - 13 May
The Mermaid at Tiny House Siesta

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 £234
includes taxes & fees
11 May - 12 May
Siesta Heron Suites & Villas

2 Bedroom Unit with Pool - 2 min walk to Siesta Beach

2 Bedroom Unit with Pool - 2 min walk to Siesta Beach
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"My husband, parents and I only stayed for three nights, but it was an absolute perfect spot for us! Very close to the beach and trolley stops to get you pretty much anywhere on Siesta Key. The place was very clean and adorably decorated. The pool and hot tub were exactly as described and made our trip even better. We Would definitely stay here again!"
United States
Melissa B.
2 Bedroom Unit with Pool - 2 min walk to Siesta Beach

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 £592
includes taxes & fees
12 May - 13 May
Mimosa | Located in Siesta Key Village w/ Heated Pool and Just Steps to Beach!

Oceanfront home w/sunset views of Sarasota Bay

Oceanfront home w/sunset views of Sarasota Bay
Vamo
9.8 out of 10, Exceptional, (125 reviews)
"Lots of seating areas so the family could spread out. "
United States
Catherine F. B.
The price is £345
includes taxes & fees
10 May - 11 May
Oceanfront home w/sunset views of Sarasota Bay

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
South Village
9.6 out of 10, Exceptional, (71 reviews)
"The room was clean and the owner was so kind! "
United States
Gloria
The price is £441
includes taxes & fees
10 May - 11 May
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly
Siesta Key Village
9.8 out of 10, Exceptional, (81 reviews)
"Loved this spot! We have stayed a MANY rentals on Siesta, this was our fave!!"
United States
wendy a.
The price is £701
includes taxes & fees
10 May - 11 May
Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

LUXURY HOUSE BY THE CANAL ☀️

LUXURY HOUSE BY THE CANAL ☀️
Siesta Key
9.6 out of 10, Exceptional, (119 reviews)
"Was very clean, easy to access, quiet and had all we needed for a great beach vacation."
United States
Denelle G.
LUXURY HOUSE BY THE CANAL ☀️

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
Siesta Key Village
9.4 out of 10, Exceptional, (19 reviews)
"Great location to walk to siesta key village. "
United States
N A.
The price is £437
includes taxes & fees
10 May - 11 May
Siesta Key Beach Duplex-Close to Sarasota Beach/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.
Save an average of 15% on thousands of hotels when you're signed in

Top Siesta Key Hotel Reviews

Find out more about Siesta Key

Siesta Key Holiday Homes information

Number of reviews
680
Accommodation
860 Holiday Homes
Lowest Price
£155
Highest Price
£701

Explore a world of travel with Expedia