Osprey Holiday Rentals, Florida: Private House Rentals

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

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Our top choices for Osprey hotels

A pathway flanked by palm trees and a building with a covered patio area.

A modern restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views of greenery.

A modern bedroom with two beds, a desk, a chair, a TV, and a balcony with a view of greenery.

A resort with a pool, sun loungers, and a wooden deck.

1. Casey Key Resorts - Mainland

Osprey

Dylan James

2.208.960 ₫

2.795.659 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A circular fire pit surrounded by a wooden pergola with cushioned seating and colorful pillows.

A spacious lobby with multiple seating areas, a large window with colorful panels, and a modern interior design.

A multi-level atrium with a central seating area, glass railings, and a large black door.

An indoor pool with a tiled wall, a clock, and a sign indicating no diving.

2. DoubleTree by Hilton Sarasota Bradenton Airport

Sarasota

Da thao

2.750.280 ₫

3.107.816 ₫ total

includes taxes & fees

27 Sept - 28 Sept

Two people sitting on a boat in the ocean at sunset.

A modern lobby with a sectional sofa, a curved seating area, and a brick accent wall.

A modern kitchen with wooden cabinets, a central island with bar stools, and a large pendant light.

A hotel room with a bed, a sofa, a desk, a chair, a TV, and a painting on the wall.

3. Hyatt Place Sarasota/Bradenton Airport

Bayou Oaks

Maria

2.574.000 ₫

2.908.621 ₫ total

includes taxes & fees

11 Oct - 12 Oct

An outdoor seating area with wicker furniture, a glass-top table, and a view of a lake and fountain.

A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.

A hotel room with a grey sofa, a small round table, a bed, and three framed pictures on the wall.

A hotel room with two beds, a nightstand, and a desk.

4. Comfort Suites Sarasota - Siesta Key

Sarasota

Carol

2.520.854 ₫

2.848.565 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.

A hotel reception area with a wooden reception desk, a large abstract mural, and a seating area with a view of greenery outside.

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a fence.

An outdoor patio with a fire feature, seating, and a bar area.

5. Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

Jose

2.431.882 ₫

2.748.027 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A hotel pool area with lounge chairs and a covered seating area.

A hotel with a central entrance, multiple floors, and a landscaped front yard with palm trees.

A spacious kitchen with a central island, built-in appliances, and a large window providing a view of the outdoors.

A spacious lobby with a reception desk, seating area, and decorative wall art.

6. Carlisle Inn

Pinecraft

Beth

3.615.786 ₫

4.085.837 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A hotel room with two beds, a desk, a chair, a TV, and a window with blinds.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A modern kitchen with dark brown cabinets, a white refrigerator, a built-in dishwasher, and a coffee maker.

A modern hotel room with a desk, office chair, sofa, TV, and dining area.

7. Holiday Inn Express Sarasota East - I-75 by IHG

Sarasota

2.418.000 ₫

2.732.340 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A spacious lobby with a central seating area, a kitchen in the background, and a large chandelier.

A hotel room with a large bed, a desk with a flat-screen TV, a chair, and a view of the outdoors.

A spacious living area with a wooden floor, teal upholstered furniture, and a central coffee table.

A modern hotel room with a kitchen area, a dining table with chairs, a sofa, and a TV.

8. Hampton Inn & Suites Venice Bayside South Sarasota

Gateway

Donna

2.963.480 ₫

3.348.732 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.

A hotel room with two beds, a sofa, a desk, a TV, and a painting on the wall.

A hotel with a covered entrance, a landscaped driveway, and palm trees.

A pool area with lounge chairs and umbrellas, surrounded by a fence and palm trees.

9. Best Western Plus Ambassador Suites Venice

Venice

Nicholas

2.162.160 ₫

2.443.240 ₫ total

includes taxes & fees

25 Sept - 26 Sept

An outdoor patio area with a covered seating area, including a round table and chairs, surrounded by potted plants and a palm tree.

A reception area with a wooden reception desk, wicker chairs, and a tiled floor.

A covered walkway with a wooden structure and lattice panels, leading to a garden area with plants and flowers.

A restaurant interior with a wooden ceiling, tables, and chairs. A sign indicates it's the first place for breakfast.

10. Island Sun Inn & Suites - Historic Venice & Beach Getaway

Venice Island

Stacy

1.430.000 ₫

1.697.020 ₫ total

includes taxes & fees

27 Sept - 28 Sept

An outdoor seating area with a stone fire pit and cushioned sofas.

A modern hotel room with a kitchenette, a bed, a desk, and a chair.

A breakfast bar with a 'Good Morning' sign, a 'Inspired Table' sign, and various breakfast items and utensils.

A hotel entrance with a red and yellow sign, palm trees, and a parking lot.

11. Home2 Suites Sarasota I-75 Bee Ridge, FL

Sarasota

Shiellha May

2.537.080 ₫

2.866.901 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A spacious lobby with a reception desk, seating area, and large windows.

A front-loading white washer and dryer unit with Tide detergent on top.

A hotel room with two beds, a nightstand, a lamp, and a large painting of a pier and sunset.

A room with two black leather chairs, a round table, and a lamp.

12. Days Inn by Wyndham Sarasota I-75

Sarasota

Jose Marcial

1.614.600 ₫

1.824.499 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A hotel room with two beds, a desk with a telephone, a chair, a sofa, a small table with a plant, and a large window offering a city view.

A hotel patio with outdoor seating, large windows, and a covered walkway.

A modern kitchen with wooden cabinets, a stainless steel sink, and a fruit display.

A modern bar area with a counter, bar stools, and pendant lighting.

13. Hyatt Place Sarasota Lakewood Ranch

Bradenton

donna

3.744.000 ₫

4.230.719 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A hotel room with a large bed, bedside tables with lamps, a chair, and a window with a view of the outside.

A hotel lobby with a reception desk, seating area, and large windows offering views of the outdoors.

A hotel with a distinctive architectural style, featuring arched windows and a prominent sign.

A modern lobby with orange chairs, a colorful rug, and a view of the outdoors.

14. Quality Inn - Near Serenoa Golf Club

Sarasota

Tanner

1.988.740 ₫

2.247.276 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A pool area with a hot tub, lounge chairs, and palm trees.

A lobby with a central glass table, four chairs, a clock, and a staircase.

A bar area with a long counter, multiple stools, and a variety of liquor bottles.

A modern outdoor seating area with wicker furniture and a large potted palm tree.

15. Ramada by Wyndham Venice Hotel Venezia

Gateway

Denise

2.574.000 ₫

2.908.621 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A beach with white lounge chairs and striped umbrellas.

A bedroom with a bed, a wooden sign above the bed, a nightstand, and a view of a garden.

A kitchen with a built-in microwave, a small refrigerator, and a wooden shelf with a coffee maker and other items.

A modern house with a patio, outdoor seating, and a view of the ocean.

16. Casey Key Resorts - Beachfront

Casey Key

Engelson

3.064.932 ₫

3.878.978 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A reception area with two illuminated reception desks, a geometric patterned wall, and a neutral-toned wall with recessed lighting.

A reception desk with a modern design, featuring a geometric wall pattern and a neutral color scheme.

A hotel lobby with a checkered floor, seating area, and a kitchen in the background.

A hotel room with two beds, a desk, and a chair.

17. Holiday Inn Express Venice by IHG

Venice

Rafael

2.408.900 ₫

2.722.057 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A neatly made bed with white linens and a blue throw blanket, flanked by two bedside tables with lamps.

A vending machine with a variety of drinks and a refrigerator.

A motel with a prominent '6' sign, a parking lot, and palm trees.

A pool area with a 3ft 9in depth, lounge chairs, and a covered seating area.

18. Motel 6 Venice, FL

Gateway

Sasha

1.480.440 ₫

1.717.560 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A pool area with a waterfall feature, lounge chairs, and palm trees.

A beach with white sand, clear blue water, and a few beach umbrellas.

A covered patio with a brick floor, wicker furniture, and tropical plants.

A pathway lined with palm trees and tropical plants, leading to a building with a white facade.

19. Tropical Beach Resorts

South Village

kurt

3.513.900 ₫

4.646.446 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A lifeguard tower with a blue roof and white walls, situated on a sandy beach with clear blue water in the background.

A round table with two green placemats, a yellow napkin, and a glass vase with a pink flower.

A hotel with a palm tree entrance, a neon sign, and a tiled roof.

A pathway leading to a white staircase surrounded by lush greenery and palm trees.

20. Inn at the Beach

Venice Island

JULIO

2.515.500 ₫

3.518.256 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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Where to stay in Osprey

Find the best Osprey areas for the activities you enjoy most.

An aerial view of a coastal area with a sandy beach, a road, and scattered buildings.

Sorrento Shores

Sorrento Shores offers an authentic slice of upscale Florida waterfront living along the peaceful Intracoastal Waterway. This residential haven gives travellers a quiet retreat from tourist crowds while still being close to attractions. The area features contemporary and Mediterranean-style homes with private docks and boat access. Water activities define life here, with excellent opportunities for kayaking, fishing, and boating right from your doorstep. The tranquil streets and gentle water sounds create a perfect atmosphere for relaxation. Nearby Oscar Scherer State Park and Nokomis Beach provide natural beauty just a short drive away.

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A river with boats, a bridge, and a cityscape with tall buildings.

Bay Acres

Bay Acres offers a tranquil waterfront retreat along Little Sarasota Bay where upscale homes line quiet streets away from tourist crowds. Travellers can enjoy boating, fishing, or simply watching spectacular sunsets over calm waters. The peaceful residential atmosphere provides an authentic glimpse into Florida coastal living. This exclusive area features Mediterranean and contemporary architecture surrounded by manicured tropical landscapes and natural beauty. While shopping and dining options require a short drive to nearby Osprey or Sarasota, the trade-off is exceptional privacy and direct access to the bay's recreational opportunities.

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Stay near popular Osprey attractions

A forest with tall trees and a dirt path.

Oscar Scherer State Park

8.8/10 (83 reviews)

A sanctuary for endangered Florida scrub-jays, Oscar Scherer State Park offers trails through diverse ecosystems. Paddle South Creek or swim in Lake Osprey after spotting wildlife in the scrubby flatwoods.

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A white wooden chapel with a triangular roof, surrounded by trees.

Historic Spanish Point

9.0/10 (42 reviews)

This 30-acre outdoor museum showcases Florida history through shell middens and pioneer buildings. Stroll through Bertha Palmer's bayfront gardens while exploring archaeological treasures spanning millennia.

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Learn more about Osprey

Paddle through Oscar Scherer State Park's serene waterways where you might spot eagles, turtles, and alligators along the way. Nearby Sarasota's white-sand beaches and Myakka River State Park offer perfect day trips from this peaceful Gulf Coast community.

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A nest on a wooden platform by a lake at sunset with birds flying around.

Top Osprey Hotel Reviews

The Ritz-Carlton, Sarasota

10/10 Excellent

"Fabulous"

Siesta Key Beach Resort and Suites

10/10 Excellent

"Amazing location super close to beach and downtown restaurants and shops. Tiki bar with live music and swing chairs was super fun. We loved the pool with zero entry and super clean air conditioned bathrooms. The added bonus of providing beach wagons, chairs and coolers was cherry on top!! Would totally stay there again!! Highly recommend."

Cottages at Siesta Key Inn

8/10 Good

"Have stayed at this location over the years"

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent

"Services was great, breakfast was really good ! Workers were ready to help me ! The only bad thing was the rack in the room was loose and the metal plate in the restroom was un attached"

Tropical Beach Resorts

10/10 Excellent

"Amazing resort,"

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good

"Room is clean and nice and close location to everything. They need to enforce the handicap parking as I could not park 3 nights in handicap and people parked there had no disabled placards"

Casey Key Resorts - Mainland

8/10 Good

"Very nice hotel. Friendly and helpful staff. Pool area is nice."

Tropical Breeze Resort

10/10 Excellent

"We had such an amazing stay at Tropical Cottages! I could not recommend this place enough and definitely see this becoming a regular vacation spot for our family. First off, the location could not be any better. You are literally steps away from the beach and a ton of restaurants! We had our 1 1/2 year old and carried him everywhere, so it was perfect to not have to wander too far to find what we needed. The beach here is UNBELIEVABLE. We grew up in South Florida and have been to several beaches throughout the state. This is 100% my favorite! The rooms were clean, comfy, and cozy. My only complaint (gotta have at least one!) is I wish there were hoses or showers outside the rooms so we could get the sand off our feet before going inside. Such a minor complaint. Everything was just so perfect about our stay and we cannot wait to return! Cannot recommend enough!!"

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent

"Perfect location for our travel baseball team for the weekend. Close enough to the multiple locations we played at and near many different food options. The staff was nice and inviting. Breakfast was good and the hotel itself was well maintained."

More cheap stays in Osprey

Days Inn by Wyndham Sarasota I-75

5774 Clark Rd Sarasota FL

1.614.600 ₫

1.824.499 ₫ total

27 Sept - 28 Sept

includes taxes & fees

6.8/10 (728 reviews)

Extended Stay America Premier Suites - Bradenton

4550 53rd Ave E Bradenton FL

1.778.140 ₫

2.009.020 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Lantern Inn & Suites

7251 N Tamiami Trl Sarasota FL

1.875.422 ₫

2.119.226 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Holiday Inn Express Sarasota East - I-75 by IHG

5730 Gantt Road Sarasota FL

2.418.000 ₫

2.732.340 ₫ total

25 Oct - 26 Oct

includes taxes & fees

8.2/10 Very good! (1,002 reviews)

Hampton Inn Sarasota - I-75 Bee Ridge

5995 Cattleridge Blvd Sarasota FL

2.537.080 ₫

2.866.901 ₫ total

4 Oct - 5 Oct

includes taxes & fees

8.8/10 Excellent! (606 reviews)

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

3.563.820 ₫

5.466.500 ₫ total

28 Sept - 29 Sept

includes taxes & fees

9.2/10 Wonderful! (1,186 reviews)

Hotels in Osprey with star rating

Frequently asked questions

What's the weather like in Osprey?

The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 19°C. Average annual precipitation for Osprey is 1126 mm.

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Book Hotels in Osprey on Expedia.com

Find hotels in Osprey, FL from 1.380.600 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Osprey

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Osprey hotels

1. Casey Key Resorts - Mainland

2. DoubleTree by Hilton Sarasota Bradenton Airport

3. Hyatt Place Sarasota/Bradenton Airport

4. Comfort Suites Sarasota - Siesta Key

5. Spark by Hilton Sarasota Siesta Key Gateway

6. Carlisle Inn

7. Holiday Inn Express Sarasota East - I-75 by IHG

8. Hampton Inn & Suites Venice Bayside South Sarasota

9. Best Western Plus Ambassador Suites Venice

10. Island Sun Inn & Suites - Historic Venice & Beach Getaway

11. Home2 Suites Sarasota I-75 Bee Ridge, FL

12. Days Inn by Wyndham Sarasota I-75

13. Hyatt Place Sarasota Lakewood Ranch

14. Quality Inn - Near Serenoa Golf Club

15. Ramada by Wyndham Venice Hotel Venezia

16. Casey Key Resorts - Beachfront

17. Holiday Inn Express Venice by IHG

18. Motel 6 Venice, FL

19. Tropical Beach Resorts

20. Inn at the Beach

Where to stay in Osprey

Sorrento Shores

Bay Acres

Stay near popular Osprey attractions

Oscar Scherer State Park

Historic Spanish Point

Learn more about Osprey

Top Osprey Hotel Reviews

The Ritz-Carlton, Sarasota

Siesta Key Beach Resort and Suites

Cottages at Siesta Key Inn

Hyatt Place Sarasota/Bradenton Airport

Tropical Beach Resorts

Spark by Hilton Sarasota Siesta Key Gateway

Casey Key Resorts - Mainland

Tropical Breeze Resort

DoubleTree by Hilton Sarasota Bradenton Airport

More cheap stays in Osprey

Days Inn by Wyndham Sarasota I-75

Extended Stay America Premier Suites - Bradenton

Lantern Inn & Suites

Holiday Inn Express Sarasota East - I-75 by IHG

Hampton Inn Sarasota - I-75 Bee Ridge

Siesta Key Beach Resort and Suites

Hotels in Osprey with star rating

Frequently asked questions

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