Search Osprey Village Cottage Rentals from CA $136

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Osprey Village Cottages

The Inn On Siesta Key
The Lookout, 1 King Bedroom 1 Bath | Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
The Inn On Siesta Key
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Terrace/patio

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (60)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is CA $272
CA $662 total
includes taxes & fees
Aug 15 - Aug 16
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Outdoor dining

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (94)
"We have stayed at this cottage before- just love this beach."
The price is CA $245
CA $592 total
includes taxes & fees
Aug 13 - Aug 14
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
On the beach, sun loungers, beach towels

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (125)
"We had an awesome vacation! The house beach and pool were outstanding. Hope to return next year!!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Terrace/patio

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

10.0 out of 10, Exceptional, (135)
"We have stayed at this cottage before, and it’s always been obvious how much love the owners put into the cottage, and how much effort they put into making your stay an enjoyable one. Knowing how much work they had to do to get it rehabbed after last year’s hurricanes makes you appreciate it even more. The cottage is very clean and has everything you need for your stay. You are right on the beach with a spectacular view of the sunset. Communication with the hosts is a breeze and they are quick...
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Terrace/patio

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"We were extremely happy with our stay and Evan as our host. He went out of his way to make sure everything went smoothly including helping us find all the beach amenities. The house was excellent and just what we needed, just a short walk across the road to the beach. We would definitely stay here again!"
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
The price is CA $205
CA $697 total
includes taxes & fees
Aug 12 - Aug 13
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
On the beach, sun loungers, beach towels

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

10.0 out of 10, Exceptional, (71)
"Wonderful quiet neighborhood property with very attentive property owners. Flamingo Cottage is ideally located for easy access to the beach as well as Shopping within walking distance. We look forward to our return next year!"
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
Property grounds

ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (23)
"Perfect place to stay. 1 mile to the village and beach access. We loved making our own meals in the grill and swimming in the pool. "
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
1-bedroom cottage just 10 minutes from Siesta Key Beach
Terrace/patio

1-bedroom cottage just 10 minutes from Siesta Key Beach

9.0 out of 10, Wonderful, (36)
"We greatly enjoyed our stay. The yard is very secluded and quite large, which was ideal for us. The house was exceptionally clean, and is well laid out. Powerful a/c system, super welcome for hot florida days. It also has a very large screened in lanai, which is perfect for relaxing. "
1-bedroom cottage just 10 minutes from Siesta Key Beach
Across The Street From #1 Beach
Exterior

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "
Across The Street From #1 Beach
Sarasota Vacation Rental w/ Private Pool & Lanai!
Interior

Sarasota Vacation Rental w/ Private Pool & Lanai!

3.0 star property
10.0 out of 10, Exceptional, (2)
"This home was great for our family. Everything was clean and well-kept. We enjoyed the pool and backyard. The home is also conveniently located with many stores and restaurants nearby."
Sarasota Vacation Rental w/ Private Pool & Lanai!
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
Exterior

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

10.0 out of 10, Exceptional, (110)
"Great place to stay. Very clean. "
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
12 Mi to Beach: Home w/ Patio & Yard in Bradenton
House (3 Bedrooms) | Interior

12 Mi to Beach: Home w/ Patio & Yard in Bradenton

3.0 star property
10.0 out of 10, Exceptional, (1)
"Clean & close to the convention center"
12 Mi to Beach: Home w/ Patio & Yard in Bradenton
Country Cottage Home
Property grounds

Country Cottage Home

9.4 out of 10, Exceptional, (140)
"Perfect place for short stay. Great little cottage in a private quiet setting. Nothing super fancy but everything you need and exceptionally clean. "
Country Cottage Home
Remodeled Siesta Key Escape – Walk to the Beach!
Exterior

Remodeled Siesta Key Escape – Walk to the Beach!

10.0 out of 10, Exceptional, (11)
"The property was great and easy communication would recommend very peaceful didn’t want to leave to be honest"
Remodeled Siesta Key Escape – Walk to the Beach!
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
Exterior

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

10.0 out of 10, Exceptional, (2)
"The property was very nice and clean. It's also in a great location - very close to the beach and the Village. I will definitely stay here again."
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
Charming tiny house with AC and WiFi in delightful Sarasota.Private and quiet.
Exterior detail

Charming tiny house with AC and WiFi in delightful Sarasota.Private and quiet.

8.0 out of 10, Very good, (1)
"Quaint little spot. Quiet and very easy to keep cool. Owner was charming. "
Charming tiny house with AC and WiFi in delightful Sarasota.Private and quiet.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (76)
"Its right next to everything we needed"
The price is CA $136
CA $417 total
includes taxes & fees
Aug 27 - Aug 28
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Dog-Friendly, Cozy Cottage, Private Patio, Walk to Bay, Near Downtown
Outdoor dining

Dog-Friendly, Cozy Cottage, Private Patio, Walk to Bay, Near Downtown

Dog-Friendly, Cozy Cottage, Private Patio, Walk to Bay, Near Downtown
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
Sign in
Sign up, it's free

Top Osprey Village Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Thank you, good experience."
Dean 3-night trip
Posted 9 hours ago
Kompose Boutique Hotel