A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Osprey vacation homes

A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is ￥15,474
￥49,271 total
includes taxes & fees
Oct 19 - Oct 20
Siesta Heron Suites & Villas
A modern kitchen with a stainless steel sink, a dining area with a table and chairs, and a living room with a sofa and a TV.

2. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (93 reviews)
"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."
United States
Ashley H.
The price is ￥42,665
￥100,500 total
includes taxes & fees
Oct 28 - Oct 29
Oceanfront home
A dining table set with plates, glasses, and a decorative glass holder.

3. Beachside Bliss: Family House-Siesta Key-3BR/2BA

Beachside Bliss: Family House-Siesta Key-3BR/2BA
Sarasota
10.0 out of 10, Exceptional, (28 reviews)
"Very clean and tucked away in a quiet little neighborhood with everything you need within 10 mins...this place made for the most comfortable and perfect vacation!"
United States
christy v.
The price is ￥15,644
￥53,880 total
includes taxes & fees
Oct 18 - Oct 19
Beachside Bliss: Family House-Siesta Key-3BR/2BA
A modern kitchen with stainless steel appliances, a dining area with a round table and chairs, and a large window overlooking a backyard.

4. KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Gulf Gate Estates
10.0 out of 10, Exceptional, (45 reviews)
"Our 2nd time here and we’ll be back again! Thanks Tim and family for such a great house!"
United States
Angela K.
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
A beach with tall grasses and a sunset.

5. 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, (38 reviews)
"This is a beautiful place."
United States
Pam J.
The price is ￥34,471
￥70,081 total
includes taxes & fees
Oct 26 - Oct 27
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
A covered patio with a round table and chairs, large windows, and a view of a backyard with a wooden fence and palm trees.

6. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key
Sarasota
9.8 out of 10, Exceptional, (85 reviews)
"Clean and convenient"
United States
Scott H.
The price is ￥18,498
￥54,602 total
includes taxes & fees
Oct 18 - Oct 19
2 miles to #1 Beach Siesta Key
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

7. Sea Turtle- Full Sized living at Tiny House Siesta

Sea Turtle- Full Sized living at Tiny House Siesta
Sarasota
9.4 out of 10, Exceptional, (18 reviews)
"The Tiny House is a perfect location to explore Siesta Key and the surrounding areas. It had just what we needed but was in close proximity (walking distance) to many bars and restaurants but was still exceptionally quiet."
United States
Wayne
The price is ￥16,276
￥30,480 total
includes taxes & fees
Oct 18 - Oct 19
Sea Turtle- Full Sized living at Tiny House Siesta
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

8. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is ￥27,654
￥52,692 total
includes taxes & fees
Oct 19 - Oct 20
The Dolphin
A beach with waves and a bird flying near the shore.

9. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."
United States
Kadina A.
The price is ￥13,748
￥27,624 total
includes taxes & fees
Oct 21 - Oct 22
The Mermaid at Tiny House Siesta
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

10. Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
Nokomis
10.0 out of 10, Exceptional, (18 reviews)
"The property was immaculate and inviting! The beds provided great comfort, and the air conditioning was just right. The house was well-equipped, with beach items being a fantastic bonus. The location is unbeatable, and the beach itself was stunning. Highly recommend—10/10!"
United States
Kimberly K.
The price is ￥22,230
￥56,876 total
includes taxes & fees
Oct 20 - Oct 21
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio
A clear swimming pool with a pink float, surrounded by a covered area with chairs and a wooden fence.

11. Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Ridge Wood Heights
9.4 out of 10, Exceptional, (128 reviews)
"Barb was very helpful and made numerous quality suggestions for nearby restaurants and activities."
United States
Mitzy B.
The price is ￥24,493
￥45,075 total
includes taxes & fees
Oct 18 - Oct 19
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

12. 3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!

3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
Gulf Gate Estates
10.0 out of 10, Exceptional, (27 reviews)
"Family had a great vacation at this property in Gulf Gate. Very nice pool and deck area and comfortable and clean home, great location for Siesta and Turtle beaches. Host was responsive and a pleasure to deal with, check in/out very simple. We were happy with our stay. "
United States
Martin F.
The price is ￥36,661
￥105,006 total
includes taxes & fees
Nov 3 - Nov 4
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!
A beach with clear blue water and a sandy shore.

13. "The Lobster" at The Shore Beach Houses Resort

"The Lobster" at The Shore Beach Houses Resort
Nokomis
10.0 out of 10, Exceptional, (3 reviews)
"Thanks so much, great space and location! Would love to come back. "
United States
Ashley
The price is ￥46,616
￥84,422 total
includes taxes & fees
Oct 31 - Nov 1
"The Lobster" at The Shore Beach Houses Resort
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

14. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 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 ￥14,486
￥47,828 total
includes taxes & fees
Oct 18 - Oct 19
[escape to paradise] siesta key beach getaway
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

15. 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 ￥17,264
￥58,081 total
includes taxes & fees
Oct 22 - Oct 23
Dolphin Villa | Pool | Steps to Siesta Key Village
A narrow hallway leading to a bathroom with a vanity, shelves with storage bins, and a chandelier.

16. Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.
Sarasota Springs
10.0 out of 10, Exceptional, (7 reviews)
"Great 1 bedroom/1 bath in a quiet neighborhood. Friendly host. Accommodations were very accurately described. There is a mini fridge which was a nice convenience to have."
United States
Larry H.
The price is ￥7,901
￥19,231 total
includes taxes & fees
Oct 24 - Oct 25
Cozy 1-bedroom private room in Sarasota.
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

17. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (222 reviews)
"Nice stay perfect location"
United States
tom f.
The price is ￥19,768
￥74,462 total
includes taxes & fees
Oct 21 - Oct 22
Siesta beach....one and only
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

18. Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
Nokomis
10.0 out of 10, Exceptional, (46 reviews)
"Great spot close to many attractions. Very well appointed with all that you need for a great vacation!"
United States
Suzanne G.
The price is ￥29,109
￥67,253 total
includes taxes & fees
Oct 20 - Oct 21
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

19. 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, (14 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is ￥16,355
￥62,260 total
includes taxes & fees
Oct 20 - Oct 21
Island Villa | Cozy Beach Retreat | Walk to Village
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

20. 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, (15 reviews)
"We loved staying here for my bachelorette!"
United States
Kelsey E.
The price is ￥20,898
￥68,386 total
includes taxes & fees
Oct 18 - Oct 19
Everglades Villa • Sleeps 8 • Walk to Siesta Beach
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 Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

8/10 Good
"I have stayed at this location several times already and I keep returning due to its location and convenience. I did have a minor issue with my room this week, the mirror over the light kept flickering, I told the front staff and they fixed it. When I returned back to my room later, it began to flicker once again. Not a huge deal because it seems like this could be normal wear and tear over time but I appreciate the staff’s promptness is addressing it. There was a water outage this trip due to a main line being cut by construction being done at the airport and the staff seemed to be very patient with customers who seemed to be frustrated about it. There wasn’t anything the hotel could do but provide bottled water in the interim but the issues was resolved some time during the night. I am returning next week and I hope check in will be smooth as I’ve had some odor issues the last 2 late check ins. Other than that, this is a great place to stay if you’re looking for convenience and friendly staff."
Brittny 3-night trip
Posted less than an hour ago
Kompose Boutique Hotel

Find out more about Osprey

Osprey Vacation Homes information

Number of reviews
783
Accommodation
3973 Vacation Homes
Lowest Price
￥19,231
Highest Price
￥105,006