Siesta Key, FL Vacation Homes from ￥32,286

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
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 vacation homes

1. Siesta Key Island Rentals

Siesta Key

Jason

￥70,902 total

includes taxes & fees

Aug 28 - Aug 29

2. Siesta Heron Suites & Villas

Siesta Key

"I feel the property was recently renovated and did not have a trial run. The 1st floor toilet water ran constantly and the water was hot, the Kuerig didn’t work, the shower shampoo/conditioner dispensers on the 2nd floor didn’t work, AC and WIFI was intermittent, no light switch in the laundry area but exposed wiring. One unit lost AC power when it was 100 degrees and they said they have no emergency service. Our back door wouldn’t open but after jiggling and resetting the improperly installed...

Tammie

￥48,702 total

includes taxes & fees

Aug 31 - Sep 1

3. [lounge like locals] walk to siesta beach +bikes

Siesta Key

Sue H.

￥49,026 total

includes taxes & fees

Aug 31 - Sep 1

4. The Mermaid at Tiny House Siesta

Sarasota

Kadina A.

￥32,286 total

includes taxes & fees

Aug 31 - Sep 1

5. Gulf Villa - 3 min to #1 Beach - Pool

Siesta Key Village

Ruben C.

￥67,695 total

includes taxes & fees

Sep 7 - Sep 8

6. Dolphin Villa - Pool - Steps to Siesta Key Village

Siesta Key Village

"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "

Sandra C.

￥56,427 total

includes taxes & fees

Aug 31 - Sep 1

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

Siesta Key Village

N A.

￥93,174 total

includes taxes & fees

Aug 31 - Sep 1

8. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Siesta Key Village

Kelsey E.

￥67,695 total

includes taxes & fees

Aug 31 - Sep 1

9. Siesta beach....one and only

Sarasota

Jennifer M.

￥74,370 total

includes taxes & fees

Sep 8 - Sep 9

10. Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

Siesta Key Village

M L.

￥70,779 total

includes taxes & fees

Aug 31 - Sep 1

11. Summer Salt – Steps to Siesta Key Village & Beach

Siesta Key Village

Brook M.

￥78,746 total

includes taxes & fees

Sep 8 - Sep 9

12. DOLPHIN PRIVATE HOUSE

Siesta Key Village

￥63,681 total

includes taxes & fees

Aug 28 - Aug 29

13. Beautiful 2 Bedroom Duplex Steps Away from the Beach

South Village

"The property is beautiful! It was everything we wanted and needed. Very clean with all the amenities. The hostess responded promptly when ever we contacted them and the check-in and out was so simple! Loved that we could walk to grab a bite to eat or just check out some shopping. The best part was the 3 min walk to the private beach which was very clean and the perfect beach for shelling! We loved this place so much we are concerning rented both 1 and 2 units next season so we can bring our...

Tajsha G.

￥95,719 total

includes taxes & fees

Aug 31 - Sep 1

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

Siesta Key

Megan C.

￥138,118 total

includes taxes & fees

Aug 28 - Aug 29

15. Salty Summer – Steps to Siesta Key Village & Beach

Siesta Key Village

Stephanie S.

￥90,814 total

includes taxes & fees

Sep 8 - Sep 9

Condo (LuLu's Key House Green 1/1 Upstairs) | Exterior

16. Lulu's Key House Green 1/1 Upstairs

Siesta Key Village

￥79,198 total

includes taxes & fees

Aug 30 - Aug 31

17. 2 Bedroom Unit with Pool - 2 min walk to Siesta Beach

Siesta Key

Melissa B.

￥67,825 total

includes taxes & fees

Aug 31 - Sep 1

18. Coastal 2 Bedroom Duplex Steps Away from the Beach

South Village

￥95,719 total

includes taxes & fees

Aug 31 - Sep 1

19. Private Beach Access w/shared Pool -Casita East

South Village

John H.

￥101,640 total

includes taxes & fees

Aug 28 - Aug 29

20. FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

South Village

Amber M.

￥104,938 total

includes taxes & fees

Aug 31 - Sep 1

View all properties

Find vacation rentals that suit your style

Private vacation homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Siesta Key Hotel Reviews

The Ringling Beach House

10/10 Excellent

"The property was perfect. The location is amazing. And Susan was the BEST!"

Tropical Breeze Resort

8/10 Good

"The property looks like it’s from an episode of Three’s Company, which is great! Pool area is nice. Our room was recently renovated. May be some lackluster renovation quality going on there, but that isn’t the fault of the property owner. They try to make up in other areas. I think the house keeping staff needs to be more responsive, but they are probably overworked. Overall a good place. You can do a lot worse. The location is excellent. They probably get things right the majority of the time. I give it 3 stars, which is much better than the average. I would stay here again."

SeaSpray Resort

10/10 Excellent

"This is a wonderful, small resort with a friendly staff and calm, quiet atmosphere. The room was spacious, very comfortable and well-kept. The pool is cute and relaxing. It’s a short walk to restaurants, and the beach is across the street. The free trolley that takes you all around is right on the corner. My family and I had a relaxing, enjoyable stay and look forward to coming back."

Captiva Beach Resort

10/10 Excellent

"Room super clean, we love it. Parking ok Kitchen ok Staff, was ok, But we have some comments that may be helpful to the property. 1 - We had problems with the door lock, the staff should be able to show how it works, or give better instructions on the welcome paperwork. 2 - We asked if there was a restroom we could use after checkout, the lady(front desk) said: NO. Only a change room. And we found out that the property have a restroom outside, close to the change room. Since we decided to stay a bit longer at the beach on Sunday the restroom would help us a lot before take 3 hours driving to final destination. She could tell us about the restroom, but she did not. Everything else was excelent! Location, quite place, clean and very confortable. Thank you."

Find out more about Siesta Key

Siesta Key Vacation Homes information

Number of reviews	389
Accommodation	900 Vacation Homes
Lowest Price	￥32,286
Highest Price	￥138,118

Explore a world of travel with Expedia

More ways to book

Book Vacation Homes in Siesta Key on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siesta Key vacation homes

1. Siesta Key Island Rentals

2. Siesta Heron Suites & Villas

3. [lounge like locals] walk to siesta beach +bikes

4. The Mermaid at Tiny House Siesta

5. Gulf Villa - 3 min to #1 Beach - Pool

6. Dolphin Villa - Pool - Steps to Siesta Key Village

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

8. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

9. Siesta beach....one and only

10. Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

11. Summer Salt – Steps to Siesta Key Village & Beach

12. DOLPHIN PRIVATE HOUSE

13. Beautiful 2 Bedroom Duplex Steps Away from the Beach

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

15. Salty Summer – Steps to Siesta Key Village & Beach

16. Lulu's Key House Green 1/1 Upstairs

17. 2 Bedroom Unit with Pool - 2 min walk to Siesta Beach

18. Coastal 2 Bedroom Duplex Steps Away from the Beach

19. Private Beach Access w/shared Pool -Casita East

20. FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

Find vacation rentals that suit your style

Top Siesta Key Hotel Reviews

The Ringling Beach House

Tropical Breeze Resort

Siesta Key Beachside Villas

SeaSpray Resort

Twin Palms at Siesta

The Capri at Siesta

Captiva Beach Resort

The Inn On Siesta Key

Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Patio

Find out more about Siesta Key

Siesta Key Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Siesta Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siesta Key vacation homes

1. Siesta Key Island Rentals

2. Siesta Heron Suites & Villas

3. [lounge like locals] walk to siesta beach +bikes

4. The Mermaid at Tiny House Siesta

5. Gulf Villa - 3 min to #1 Beach - Pool

6. Dolphin Villa - Pool - Steps to Siesta Key Village

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

8. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

9. Siesta beach....one and only

10. Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

11. Summer Salt – Steps to Siesta Key Village & Beach

12. DOLPHIN PRIVATE HOUSE

13. Beautiful 2 Bedroom Duplex Steps Away from the Beach

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

15. Salty Summer – Steps to Siesta Key Village & Beach

16. Lulu's Key House Green 1/1 Upstairs

17. 2 Bedroom Unit with Pool - 2 min walk to Siesta Beach

18. Coastal 2 Bedroom Duplex Steps Away from the Beach

19. Private Beach Access w/shared Pool -Casita East

20. FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

Find vacation rentals that suit your style

Top Siesta Key Hotel Reviews

The Ringling Beach House

Find out more about Siesta Key

Siesta Key Vacation Homes information

Explore a world of travel with Expedia