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

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Our top choices for Osprey holiday 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.

A wooden deck overlooking a calm river, surrounded by lush greenery and trees.

A spacious living area with a large bed, a sofa, a small table, and a kitchen in the background.

A modern kitchen with white cabinets, a black countertop, and a red coffee maker.

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 star property

Siesta Key

8.4 out of 10, Very good, (46 reviews)

8.4/10

Very good

(46 reviews)

"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"

Christopher Robert

The price is €289

€289

includes taxes & fees

2 Nov - 3 Nov

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.

A modern living room with a sofa, coffee table, and dining area with chairs and a table.

A modern living room with a sofa, dining table, and bar stools. A kitchen with white cabinets and a refrigerator is visible in the background.

A swimming pool with lounge chairs and palm trees.

2. Oceanfront home

Oceanfront home

Vamo

9.8 out of 10, Exceptional, (94 reviews)

9.8/10

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."

Ashley H.

Oceanfront home

A dining table set with plates, glasses, and a decorative glass holder.

An outdoor patio with wicker furniture, a striped umbrella, and a view of a backyard with a fence and trees.

A modern kitchen with wooden cabinets, stainless steel appliances, granite countertops, and a central island with seating.

A kitchen with wooden cabinets, a coffee bar sign, a coffee maker, a basket, and a salt and pepper set.

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)

10/10

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!"

christy v.

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

A wooden deck with a railing overlooking a lake, surrounded by lush greenery.

A modern kitchen with stainless steel appliances, a central island with bar stools, and a large window providing natural light.

A sign for Siesta Beach, a Sarasota County Park, located at 948 Beach Road.

4. 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)

9.2/10

Wonderful

(38 reviews)

"This is a beautiful place."

Pam J.

The price is €393

€393

includes taxes & fees

26 Oct - 27 Oct

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

A bedroom with a bed, nightstand, lamp, and a ceiling fan.

A living room with a sofa, a TV, a small table, and a chair. There is a door leading to another room.

A covered patio area with a blue sofa and a table, a wooden sculpture, and a dolphin wall art piece.

5. The Dolphin

The Dolphin

Nokomis

9.8 out of 10, Exceptional, (21 reviews)

9.8/10

Exceptional

(21 reviews)

"The cottage was comfortable and the pool was relaxing. "

daniel

The price is €302

€302

includes taxes & fees

24 Oct - 25 Oct

The Dolphin

A compact kitchen with a built-in dishwasher, a granite countertop, and a ceiling fan.

A sandy pathway flanked by palm trees and modern buildings with balconies.

An aerial view of a coastal area with a beach, a hotel with multiple floors, and a highway nearby.

A swimming pool with lounge chairs and palm trees, surrounded by a hotel building with multiple balconies.

6. 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)

9.2/10

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!"

Amber M.

The price is €617

€617

includes taxes & fees

24 Oct - 25 Oct

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

A compact, well-lit interior with a bunk bed, seating area, kitchenette, and a television.

A compact, modern interior with a loft bedroom, a seating area with a laptop, and a kitchenette.

A compact kitchen with wooden cabinets, a built-in seating area, a television, and a small table with a tablet.

A wooden deck with a welcome sign, outdoor seating, and a covered area with chairs and tables.

7. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta

Sarasota

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."

Kadina A.

The Mermaid at Tiny House Siesta

A modern kitchen with a central island, a dining area with a table and chairs, and a living area with a sofa and a wall-mounted TV.

A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

A compact kitchen with a refrigerator, microwave, and sink, a small dining area with a white table and two chairs, and a sofa with a floral pattern.

An outdoor seating area with a 'WELCOME' sign, wooden benches, and a blue chair.

8. 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)

9.4/10

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."

Wayne

The price is €194

€194

includes taxes & fees

22 Nov - 23 Nov

Sea Turtle- Full Sized living at Tiny House Siesta

A modern kitchen with white cabinets, a dining area with wicker chairs and a glass table, and a large window with a view.

A modern living room with a wooden ceiling, a beige sofa, two armchairs, a coffee table, and large windows with blinds.

A coastal residential area with houses, a marina, and a clear view of the ocean.

A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

9. 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)

10/10

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!"

Kimberly K.

The price is €325

€325

includes taxes & fees

24 Oct - 25 Oct

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

A modern kitchen with a white countertop, wooden stools, and a potted plant.

A modern kitchen with a central island, bar stools, and built-in appliances.

A modern living room with a grey sofa, ottoman, and a flat-screen TV mounted on the wall.

10. 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)

10/10

Exceptional

(46 reviews)

"Great spot close to many attractions. Very well appointed with all that you need for a great vacation!"

Suzanne G.

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

A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

A modern kitchen with a dining area, featuring a white countertop, blue cabinets, and a round table with chairs.

A modern living room with a flat-screen TV, teal armchairs, a striped rug, and a white cabinet with yellow items.

A modern kitchen with white cabinets, a blue countertop, and a dining area with a round table and grey chairs.

11. 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)

9.4/10

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. "

Amy

The price is €339

€339

includes taxes & fees

31 Oct - 1 Nov

Dolphin Villa | Pool | Steps to Siesta Key Village

A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

A modern living room with a large flat-screen TV mounted on the wall, a wooden coffee table, two sofas, and decorative plants.

A residential property at night with a swimming pool, a covered patio, and a car parked in the driveway.

A dining area with a wooden table set for four, surrounded by cushioned chairs.

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)

10/10

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. "

Martin F.

The price is €604

€604

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!

A covered patio with a ceiling fan, white chairs, and a glass table.

A residential area with houses, palm trees, and a view of the ocean.

A modern kitchen with white cabinetry, a built-in microwave, and a large oven.

A dining area with a glass table, chairs, and a buffet bowl. There is a sofa and a ceiling fan in the background.

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

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

Siesta Key Village

9.6 out of 10, Exceptional, (22 reviews)

9.6/10

Exceptional

(22 reviews)

"Beautiful little place. Super clean. Has everything you need. Great communication and quick response to any need. Fast walk to the beach and village."

Ivette R.

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

A bedroom with a bed, a desk, a chair, a ceiling fan, and a door leading to a bathroom.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a coffee maker. There are two blue chairs and a small table with bottles.

A glass-enclosed patio with a table and chairs, a ceiling fan, and a view of the backyard.

A living room with a sofa set, a wooden table, a ceiling fan, and a TV mounted on the wall.

14. "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)

10/10

Exceptional

(3 reviews)

"Thanks so much, great space and location! Would love to come back. "

Ashley

The price is €492

€492

includes taxes & fees

31 Oct - 1 Nov

"The Lobster" at The Shore Beach Houses Resort

A clear swimming pool with a pink float, surrounded by a covered area with chairs and a wooden fence.

A kitchen with a dining area, wooden cabinets, a black refrigerator, and a window with blinds.

A bedroom with a bed, a ceiling fan, a window with curtains, a floor lamp, and a painting on the wall.

A house with a red door, a patio with chairs, and a garden with tropical plants.

15. 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)

9.4/10

Exceptional

(128 reviews)

"Beautiful home, perfect location! Would come back again. Thank you!!! "

Joe V.

The price is €254

€254

includes taxes & fees

25 Oct - 26 Oct

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

A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

A modern living room with a grey sectional sofa, yellow cushions, a small round table, and a wicker basket.

A bedroom with a bed, bedside tables, a ceiling fan, and curtains.

A modern living room with a sectional sofa, a dining area with yellow curtains, a kitchen with white cabinets, and a ceiling fan.

16. [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)

9.8/10

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."

Moreixa C.

The price is €282

€282

includes taxes & fees

25 Oct - 26 Oct

[lounge like locals] walk to siesta beach +bikes

A modern dining area with a long table, chairs, and a ceiling light fixture.

A swimming pool with lounge chairs and an umbrella, surrounded by a white fence and a building with large windows.

A lifeguard tower with a red exterior, a flagpole with an American flag, and a beach with people and buildings in the background.

17. Poolside Paradise Near Siesta Key Beach

Poolside Paradise Near Siesta Key Beach

Bee Ridge

8.8 out of 10, Excellent, (13 reviews)

8.8/10

Excellent

(13 reviews)

"Our family of 11 had a truly wonderful stay. The pool was most definitely a highlight."

Fannie Marie S.

Poolside Paradise Near Siesta Key Beach

A house with a 'WELCOME' sign, a covered patio, a covered patio, and a gravel driveway.

A white exterior wall with a metal pipe, a white door, and a potted plant with purple leaves.

A bedroom with a bed, a television, a desk, and a sliding glass door leading to a patio.

A bathroom with a bathtub, toilet, vanity with a sink, mirror, and a toilet paper holder.

18. Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.

Sarasota Springs

10.0 out of 10, Exceptional, (7 reviews)

10/10

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."

Larry H.

The price is €112

€112

includes taxes & fees

29 Oct - 30 Oct

Cozy 1-bedroom private room in Sarasota.

A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

A spacious living room with a high ceiling, a ceiling fan, a dining area with orange chairs, and a large gray sofa.

A modern kitchen with white cabinets, a coffee maker, and a sink. There is a window with blinds and a door leading to a balcony.

A modern kitchen with white cabinets, a central island, and a dining area with orange chairs and a red table.

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)

8.4/10

Very good

(14 reviews)

"Great place to stay and very close to restaurants "

Amber B.

Island Villa | Cozy Beach Retreat | Walk to Village

An aerial view of a beach with clear skies, a sandy shore, and a mix of greenery and paths.

A kitchen with a central island, stainless steel appliances, and a red accent wall.

A spacious living room with a white sofa, a glass coffee table, and a ceiling fan.

20. Pet Friendly home, Close to Sarasota Beach!

Pet Friendly home, Close to Sarasota Beach!

Siesta Key Village

9.0 out of 10, Wonderful, (8 reviews)

9.0/10

Wonderful

(8 reviews)

"Great house great location will definitely come back to this property "

Matthew Y.

Pet Friendly home, Close to Sarasota 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

10/10 Excellent

"Very clean and great location."

Melissa 4-night trip

Posted 1 hour ago

Kompose Boutique Hotel

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"I liked that the yogurt was from Westby Cremery"

Sally 1-night trip

Posted 3 hours ago

Spark by Hilton Sarasota Siesta Key Gateway

Tropical Beach Resorts

10/10 Excellent

"I loved how close to the private beach this property was. We walked to the beach in under 5 min. It's a lovely beach. It was also nice to have a kitchen to cook our own food."

Sonja 2-night trip

Posted 5 hours ago

Tropical Beach Resorts

EVEN Hotel Sarasota-Lakewood Ranch by IHG

10/10 Excellent

"It was nice and clean. Much more affordable. Could use more of a selection of bourbon."

Nathan 1-night trip

Posted 9 hours ago

EVEN Hotel Sarasota-Lakewood Ranch by IHG

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent

"Clean rooms, nice staff and breakfast was so nice"

Alexandra 1-night trip

Posted 1 day ago

Hyatt Place Sarasota/Bradenton Airport

Embassy Suites by Hilton Sarasota, FL

8/10 Good

"Breakfast very good"

steve 7-night trip

Posted 1 day ago

Embassy Suites by Hilton Sarasota, FL

Casey Key Resorts - Mainland

10/10 Excellent

"Deluxe room was nice and spacious. Very clean. Nice pool and bar. Pizza was delicious!"

Christine 5-night trip

Posted 1 day ago

Casey Key Resorts - Mainland

Lido Beach Resort

8/10 Good

"The lower priced rooms are the older part of the resort. They show their age. I suggest spending more on your stay to get a room in the newer high rise part of the resort."

Joseph 3-night trip

Posted 1 day ago

Lido Beach Resort

The Ritz-Carlton, Sarasota

10/10 Excellent

"Best hotel I’ve ever stayed at. The staff was amazing. Ready to help at all times! The spa was fantastic, as well as the Beach Club!"

Michael 3-night trip

Posted 3 days ago

The Ritz-Carlton, Sarasota

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews	413
Accommodation	3944 Holiday Homes
Lowest Price	€112
Highest Price	€617

Holiday Homes in Osprey

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osprey holiday homes

1. Siesta Heron Suites & Villas

2. Oceanfront home

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

4. Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

5. The Dolphin

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

7. The Mermaid at Tiny House Siesta

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

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

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

11. Dolphin Villa | Pool | Steps to Siesta Key Village

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

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

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

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

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

17. Poolside Paradise Near Siesta Key Beach

18. Cozy 1-bedroom private room in Sarasota.

19. Island Villa | Cozy Beach Retreat | Walk to Village

20. Pet Friendly home, Close to Sarasota Beach!

Find holiday rentals that suit your style

Top Osprey Hotel Reviews

Kompose Boutique Hotel

Find out more about Osprey

Osprey Holiday Homes information