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 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.

A modern reception area with a wooden reception desk, a flat-screen TV, and a sign for Casey Key Resorts Mainland.

1. Casey Key Resorts - Mainland

Osprey

Alecssandre

1.639.250 ₫

2.074.635 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A swimming pool with a 3 ft 3 in depth marker, surrounded by lounge chairs and a covered seating area with a view of the water.

A sandy beach path with wooden posts and ropes, leading towards the ocean.

A wooden deck with chairs and a table overlooking a body of water.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a marble island.

2. Turtle Beach Resort

Siesta Key

Susan

5.244.901 ₫

6.677.026 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A hotel lobby with a reception desk, a refrigerator with beverages, and a microwave.

3. Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

Gaeliel

2.463.066 ₫

2.783.266 ₫ total

includes taxes & fees

15 Oct - 16 Oct

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

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

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.

4. Tropical Beach Resorts

South Village

kurt

3.290.918 ₫

4.391.150 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.

A conference room with a long table, blue chairs, framed artwork on the walls, and a Holiday Inn Express sign.

A modern lobby with a sofa, chairs, a desk, and a map mural on the wall.

A modern hotel corridor with a wooden reception desk, a staircase, and a snack bar with various packaged goods.

5. Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Nokomis

Lisa

2.613.072 ₫

2.952.772 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A hotel with a covered outdoor seating area, palm trees, and a sign reading "HOME 2".

A hotel room with a sofa, a desk, a lamp, a television, and a window with patterned curtains.

A breakfast area with a buffet setup, including a coffee machine, bowls, and a variety of food items.

A compact kitchen with a microwave, sink, and dishwasher.

6. Home2 Suites by Hilton Nokomis Sarasota Casey Key

Nokomis

nathali

3.394.761 ₫

3.836.080 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A rooftop terrace with a fire feature, seating area, and a view of the city skyline.

A modern lobby with a vertical garden, seating area, and a bar.

A modern restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.

A modern lobby with a vertical garden, comfortable seating, and a geometric light fixture.

7. The Westin Sarasota

Central Sarasota

THANG

6.700.848 ₫

8.215.136 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

A hotel breakfast area with a self-service station, a refrigerator with beverages, and a wall-mounted sign.

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.

8. Comfort Suites Sarasota - Siesta Key

Sarasota

Jymieka

2.616.953 ₫

2.957.157 ₫ total

includes taxes & fees

18 Oct - 19 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 modern hotel room with a kitchen area, a dining table with chairs, a sofa, and a TV.

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

9. Hampton Inn & Suites Venice Bayside South Sarasota

Gateway

Donna

3.276.689 ₫

3.702.659 ₫ total

includes taxes & fees

16 Oct - 17 Oct

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 hotel room with two beds, a kitchenette, a TV, and a desk.

10. Carlisle Inn

Pinecraft

Darrel

3.704.870 ₫

4.186.503 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

A hotel lobby with two brown sofas, a red sofa with gold patterns, a coffee station, and a reception desk.

11. Best Western Plus Ambassador Suites Venice

Venice

Nicholas

1.921.255 ₫

2.171.017 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A rectangular swimming pool with white lounge chairs on both sides, surrounded by palm trees and a wooden fence.

An aerial view of a coastal area with a sandy beach, a row of houses, and a clear sky.

A modern kitchen with white cabinets, a granite countertop, and a built-in dishwasher.

A living room with a TV, white cabinets, a sofa, and a balcony with a view.

12. Escape Coastal Resort on Casey Key

Casey Key

Melissa

2.046.193 ₫

3.923.997 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

A beach scene with a hammock, palm trees, and the sun setting over the ocean.

A living room with a sofa, coffee table, and a dining area with chairs. There is a sign on the wall and a painting above the sofa.

A room with a large window overlooking a beach, a small table with a placemat, and a chair with a decorative backrest.

13. A Beach Retreat

Casey Key

Genghis

4.767.433 ₫

5.387.326 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A room with a blue patterned wall, a wooden floor, a blue sofa, a wooden bench, and a bed with a white headboard.

A bedroom with a bed, a TV, a wooden dresser, and a bathroom visible through an open door.

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a multi-story building.

14. Cottages at Siesta Key Inn

South Village

Cassie

3.047.981 ₫

3.857.525 ₫ 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 hotel room with a desk, chair, sofa, and a TV.

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

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

Sarasota

CARLOS

1.970.984 ₫

2.227.211 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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

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

A swimming pool with a white pergola overhead, surrounded by lounge chairs and umbrellas.

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

16. Inn at the Beach

Venice Island

Christina

3.706.940 ₫

4.861.255 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A rocky beach with large boulders in the foreground and a clear blue sky.

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

A hotel room with a round wooden table, two beige armchairs, a large painting of a forest, a ceiling light, and a window with curtains.

17. Fairfield Inn & Suites by Marriott Venice

Venice

Maritza

2.530.640 ₫

2.859.623 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel room with a large bed, a desk, and a view of the ocean.

A restaurant with round tables and chairs, large windows, and a view of palm trees.

A hotel room with two beds, a large mirror, a TV, and a balcony with curtains.

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a clear blue sky.

18. Cirque St. Armands Beachside

Lido Key

Yuliesvy

6.700.848 ₫

8.595.196 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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

19. Days Inn by Wyndham Sarasota I-75

Sarasota

crystal

1.606.651 ₫

1.815.515 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

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

A narrow concrete pathway flanked by white walls, leading to a lush green area with palm trees and a small grassy patch.

A modern living room with a flat-screen TV, a round coffee table, and a sofa.

20. SeaSpray Resort

Siesta Key

Rommel

5.797.915 ₫

6.551.825 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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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.

See all hotels in Osprey

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

Top Osprey Hotel Reviews

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent

"Checking in was easy. Staff was very nice. Rooms were clean and spacious"

Kompose Boutique Hotel

10/10 Excellent

"Love staying at the Kompose! Great staff!! Amazing rooms!! Breakfast is 👍👍"

The St. Regis Longboat Key Resort

10/10 Excellent

"Beach view and staff"

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"I’m"

Lido Beach Resort

10/10 Excellent

"Great place- wonderful staff"

Carlisle Inn

10/10 Excellent

"Very nice hotel. Very clean and well-maintained. Our room was spacious and well appointed. Management and employees were friendly and engaging. The pool area was nice and could accommodate several different families at the same time. The breakfast was slightly underwhelming. If you are expecting a Der Dutchman style breakfast prepare to be disappointed. The breakfast had a few Amish-style baked goods (doughnuts, apple fritters, cinnamon rolls) but other than that I would compare it to a Holiday Inn Express or Fairfield Inn. They served biscuits both days we were there but no gravy which was a real disappointment. I tasted the eggs one morning and they were very good, not dry and rubbery like some hotels."

Casey Key Resorts - Mainland

10/10 Excellent

"Front desk was very friendly!"

Tropical Breeze Resort

8/10 Good

"Great location, close to restaurants and shops."

Cottages at Siesta Key Inn

10/10 Excellent

"Great weekend stay at siesta!"

More cheap stays in Osprey

Days Inn by Wyndham Sarasota I-75

5774 Clark Rd Sarasota FL

1.606.651 ₫

1.815.515 ₫ total

14 Oct - 15 Oct

includes taxes & fees

Holiday Inn Express Sarasota East - I-75 by IHG

5730 Gantt Road Sarasota FL

1.970.984 ₫

2.227.211 ₫ total

21 Oct - 22 Oct

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Extended Stay America Premier Suites - Bradenton

4550 53rd Ave E Bradenton FL

2.002.234 ₫

2.262.248 ₫ total

28 Oct - 29 Oct

includes taxes & fees

8.8/10 Excellent! (796 reviews)

Lantern Inn & Suites

7251 N Tamiami Trl Sarasota FL

2.030.434 ₫

2.294.390 ₫ total

18 Oct - 19 Oct

includes taxes & fees

Hampton Inn Sarasota - I-75 Bee Ridge

5995 Cattleridge Blvd Sarasota FL

2.616.953 ₫

2.957.157 ₫ total

19 Oct - 20 Oct

includes taxes & fees

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

3.784.297 ₫

5.708.915 ₫ total

11 Oct - 12 Oct

includes taxes & fees

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 1.815.515 ₫

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. Turtle Beach Resort

3. Spark by Hilton Sarasota Siesta Key Gateway

4. Tropical Beach Resorts

5. Holiday Inn Express & Suites Nokomis Sarasota South by IHG

6. Home2 Suites by Hilton Nokomis Sarasota Casey Key

7. The Westin Sarasota

8. Comfort Suites Sarasota - Siesta Key

9. Hampton Inn & Suites Venice Bayside South Sarasota

10. Carlisle Inn

11. Best Western Plus Ambassador Suites Venice

12. Escape Coastal Resort on Casey Key

13. A Beach Retreat

14. Cottages at Siesta Key Inn

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

16. Inn at the Beach

17. Fairfield Inn & Suites by Marriott Venice

18. Cirque St. Armands Beachside

19. Days Inn by Wyndham Sarasota I-75

20. SeaSpray Resort

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

Hyatt Place Sarasota/Bradenton Airport

Kompose Boutique Hotel

The St. Regis Longboat Key Resort

Spark by Hilton Sarasota Siesta Key Gateway

Lido Beach Resort

Carlisle Inn

Casey Key Resorts - Mainland

Tropical Breeze Resort

Cottages at Siesta Key Inn

More cheap stays in Osprey

Days Inn by Wyndham Sarasota I-75

Holiday Inn Express Sarasota East - I-75 by IHG

Extended Stay America Premier Suites - Bradenton

Lantern Inn & Suites

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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