Holiday Homes in Siesta Key

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Our top choices for Siesta Key holiday homes

[Tropical] guesthouse retreat on Siesta Key

[Tropical] guesthouse retreat on Siesta Key
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"Great. Was very responsive "
United States
Mark B.
[Tropical] guesthouse retreat on Siesta Key

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (25 reviews)
"Clean and comfortable. "
United States
Laney
The price is €261
includes taxes & fees
15 Feb - 16 Feb
[escape to paradise] siesta key beach getaway

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (2 reviews)
"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."
United States
Jackeline R.
The price is €188
includes taxes & fees
8 Feb - 9 Feb
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, (39 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
The price is €499
includes taxes & fees
12 Feb - 13 Feb
Siesta Heron Suites & Villas

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
Beachy Sarasota Duplex

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (58 reviews)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is €387
includes taxes & fees
5 Feb - 6 Feb
Siesta Key Island Rentals

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, (26 reviews)
"Great place close to everything"
United States
Tracey M.
SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

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, (3 reviews)
"Very nice. Walking distance to beach and restaurants"
United States
Mark P.
The price is €526
includes taxes & fees
5 Feb - 6 Feb
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport

3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport
Siesta Key
8.8 out of 10, Excellent, (11 reviews)
The price is €200
includes taxes & fees
26 Feb - 27 Feb
3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport

Waterfront Heated Pool House Kayaks Boat Dock

Waterfront Heated Pool House Kayaks Boat Dock
2.0 star property
Siesta Key
Waterfront Heated Pool House Kayaks Boat Dock

Tiny House Blue Lifeguard - pet friendly

Tiny House Blue Lifeguard - pet friendly
Sarasota
7.4 out of 10, Good, (3 reviews)
"The process was 100% contactless and easy. The tiny home was cute and clean for the most part but it is in disrepair and needs deep cleaning. There was mold in the shower (like a lot) on the knobs and walls. Also, the floorboards were weak under the bathroom and it felt like it was caving in. (I am not a large or heavy person). One of the pillow covers had a blood stain, and there was a thick layer of dust on the art throughout the unit. The little community was very cute. I’d stay again for...
United States
April S.
Tiny House Blue Lifeguard - pet friendly

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, (13 reviews)
"Great location, clean, good communication. "
United States
Alexandra P.
The price is €585
includes taxes & fees
11 Feb - 12 Feb
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

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

Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Siesta Key
9.0 out of 10, Wonderful, (44 reviews)
"Very nice property! Beautiful beach! We had a problem with one of the showers and it was solved right away.The communication with the management was excellent , they reached to us several times though texts to make sure everything was ok.We highly recommend this property!"
United States
Fernanda L.
Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Private Beach Access w/shared Pool -Casita East

Private Beach Access w/shared Pool -Casita East
South Village
10.0 out of 10, Exceptional, (2 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.
Private Beach Access w/shared Pool -Casita East

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

NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS
South Village
9.4 out of 10, Exceptional, (44 reviews)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
The price is €248
includes taxes & fees
8 Feb - 9 Feb
NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS

Pet Friendly home, Close to Sarasota Beach!

Pet Friendly home, Close to Sarasota Beach!
Siesta Key Village
9.4 out of 10, Exceptional, (6 reviews)
"Great house great location will definitely come back to this property "
United States
Matthew Y.
Pet Friendly home, Close to Sarasota Beach!

[Relax by the Pool] on Siesta Key

[Relax by the Pool] on Siesta Key
Siesta Key
9.0 out of 10, Wonderful, (16 reviews)
"Nice spot for a short stay"
United States
scott k.
[Relax by the Pool] on Siesta Key

Tropical 2BR Duplex • 5 Min to Siesta Key Beach

Tropical 2BR Duplex • 5 Min to Siesta Key Beach
Sarasota
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing stay! The home was clean, comfortable, and beautifully set up with everything we needed. The tropical vibe really made it feel like a vacation, and the location was perfect—just minutes from Siesta Key Beach. The host was very responsive and welcoming, which made the stay even better. We would absolutely stay here again and highly recommend it to anyone visiting the area."
United States
Matt A.
Tropical 2BR Duplex • 5 Min to Siesta Key Beach

Newly Renovated Beach-Side villa | Pool | Dock

Newly Renovated Beach-Side villa | Pool | Dock
Siesta Key Village
9.4 out of 10, Exceptional, (14 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
Newly Renovated Beach-Side villa | Pool | Dock

Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
The price is €1,221
includes taxes & fees
28 Feb - 1 Mar
Lulu's Key House Leatherback 2/2 Downstairs
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

Siesta Key Holiday Homes information

Number of reviews
293
Accommodation
899 Holiday Homes
Lowest Price
€188
Highest Price
€1,221

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