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

Holiday Homes in Osprey

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Our top choices for Osprey holiday homes

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 NZ$547
includes taxes & fees
22 Oct - 23 Oct
Siesta Heron Suites & Villas

2. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (94 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.
Oceanfront home

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 NZ$590
includes taxes & fees
29 Oct - 30 Oct
Beachside Bliss: Family House-Siesta Key-3BR/2BA

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

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 NZ$775
includes taxes & fees
26 Oct - 27 Oct
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

6. 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 NZ$310
includes taxes & fees
22 Oct - 23 Oct
The Mermaid at Tiny House Siesta

7. Updated Beach House. Walk to Beach, Shop, Waterfront Dining 2 Bed 1 Bath

Updated Beach House. Walk to Beach, Shop, Waterfront Dining 2 Bed 1 Bath
Nokomis
10.0 out of 10, Exceptional, (10 reviews)
"Great stay, good location, attentive host!"
United States
Ashley E.
Updated Beach House. Walk to Beach, Shop, Waterfront Dining 2 Bed 1 Bath

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 NZ$584
includes taxes & fees
22 Oct - 23 Oct
The Dolphin

9. 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 NZ$340
includes taxes & fees
22 Oct - 23 Oct
Sea Turtle- Full Sized living at Tiny House Siesta

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 NZ$630
includes taxes & fees
22 Oct - 23 Oct
Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

11. The Sea Turtle

The Sea Turtle
Nokomis
9.4 out of 10, Exceptional, (17 reviews)
"Great place, awesome warm pool. Perfect location !"
United States
Jerry I.
The price is NZ$562
includes taxes & fees
22 Oct - 23 Oct
The Sea Turtle

12. 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 NZ$655
includes taxes & fees
31 Oct - 1 Nov
Dolphin Villa | Pool | Steps to Siesta Key Village

13. 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 NZ$1,156
includes taxes & fees
3 Nov - 4 Nov
3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!

14. 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 NZ$215
includes taxes & fees
24 Oct - 25 Oct
Cozy 1-bedroom private room in Sarasota.

15. "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 NZ$915
includes taxes & fees
21 Nov - 22 Nov
"The Lobster" at The Shore Beach Houses Resort

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

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
South Village
9.2 out of 10, Wonderful, (7 reviews)
"We had an incredible stay and this is such a great option IN siesta Key that is close to the beaches, has private beach access and is a stand alone building. The unit also has an outdoor shower which was such a great surprise. We will be back!"
United States
Amber M.
The price is NZ$1,175
includes taxes & fees
22 Oct - 23 Oct
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

17. 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)
"Beautiful home, perfect location! Would come back again. Thank you!!! "
United States
Joe V.
The price is NZ$495
includes taxes & fees
22 Oct - 23 Oct
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

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

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is NZ$505
includes taxes & fees
22 Oct - 23 Oct
[lounge like locals] walk to siesta beach +bikes

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.
Island Villa | Cozy Beach Retreat | Walk to Village

20. 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 NZ$769
includes taxes & fees
22 Oct - 23 Oct
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
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

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
455
Accommodation
3973 Holiday Homes
Lowest Price
NZ$215
Highest Price
NZ$1,175