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

Osprey Vacation Rentals

Q: What are some of the best vacation rentals in Osprey?

Tropical Villas of Venice Beach : This vacation home rental near Osprey is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

Dates

November 2026

December 2026

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Our top choices for Osprey vacation rentals

An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees visible in the foreground.

1. Charming Osprey Home

Bay Acres

Diane S.

AED 1,386 total

includes taxes & fees

10 Nov - 11 Nov

An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees in the foreground.

2. Sunny Coastal Escape

Bay Acres

Jennifer A.

AED 1,544 total

includes taxes & fees

10 Nov - 11 Nov

A tented accommodation with a bed, pillows, a desk, and chairs.

3. Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Sarasota

A tented accommodation with a central bed, bedside tables, a hanging light fixture, and a patterned floor.

4. Charming Secluded Tented Cabin in Sarasota, Florida

Sarasota

AED 1,312 total

includes taxes & fees

10 Nov - 11 Nov

5. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Sarasota

A tent with two chairs and a checkered mat in a forest.

6. Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Sarasota

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

7. Tropical Beach Resorts

South Village

Christine

AED 695 total

includes taxes & fees

10 Nov - 11 Nov

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

8. A Beach Retreat

Casey Key

Robin

AED 765 total

includes taxes & fees

6 Dec - 7 Dec

An outdoor patio with a grill, white chairs, and a red umbrella.

9. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

AED 556 total

includes taxes & fees

15 Nov - 16 Nov

A compact living space with a sofa, a television, a ceiling fan, and a door.

10. Tiny House Siesta

Sarasota

Staci

AED 747 total

includes taxes & fees

22 Nov - 23 Nov

A beach with white sand, wooden beach chairs, and a clear blue sky.

11. Captiva Beach Resort

South Village

Andriy

AED 757 total

includes taxes & fees

6 Dec - 7 Dec

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.

12. Oceanfront home

Vamo

Ashley H.

AED 2,266 total

includes taxes & fees

15 Nov - 16 Nov

A wooden structure with a thatched roof overlooking a beach.

13. Casey Key Resort

Casey Key

Jamie

AED 881 total

includes taxes & fees

2 Dec - 3 Dec

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.

14. SeaSpray Resort

Siesta Key

Geraldine

AED 902 total

includes taxes & fees

11 Nov - 12 Nov

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

15. The Dolphin

Nokomis

daniel

AED 810 total

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a bed, a dresser, a television, a painting, and a chair.

16. 2 Miles to Siesta Key

Gulf Gate Estates

Keith K.

A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

17. Bright & Beachy–Beach Club Siesta Key 100A by RVA

South Village

Evan C.

AED 1,203 total

includes taxes & fees

4 Dec - 5 Dec

A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

18. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

South Village

maureen p.

AED 1,281 total

includes taxes & fees

20 Nov - 21 Nov

A wooden boardwalk leading to a beach with a clear blue sky.

19. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key

kelly h.

AED 1,756 total

includes taxes & fees

10 Nov - 11 Nov

A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

20. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

South Village

James J.

AED 810 total

includes taxes & fees

10 Nov - 11 Nov

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Find vacation rentals that suit your style

Top Osprey Hotel Reviews

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

Casey Key Resorts - Mainland

Osprey

10/10 Excellent

Marilyn

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

Escape Coastal Resort on Casey Key

Casey Key

10/10 Excellent

paul

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

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Nokomis

10/10 Excellent

Linda

A covered outdoor area with a pool, lounge chairs, and a wooden deck.

Siesta Key Palms Resort

Sarasota

10/10 Excellent

Lori

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.

Turtle Beach Resort

Siesta Key

10/10 Excellent

kaitlyn

A pool area with lounge chairs, palm trees, and a building with balconies.

Siesta Key Inn

South Village

10/10 Excellent

Jerome

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

Home2 Suites by Hilton Nokomis Sarasota Casey Key

Nokomis

10/10 Excellent

My mom and I enjoyed our stay here and will definitely come back. We were Inn Florida for the Diana Ross concert in Sarasota but all of the hotels were pretty expensive. Nokimis is less than 30 minutes from Sarasota so we decided to stay here. I was very pleased as I am very picky when it comes to hotels. The hotel itself is pretty new (less than 2 months) and the room was spacious and very clean. The front desk reps were very nice and the complementary continental breakfast was great! ...

Tomesha

Tropical Beach Resorts

South Village

10/10 Excellent

Heather

A hotel with a pool, palm trees, and a sign reading "Twin Palms."

Twin Palms at Siesta

Siesta Key

10/10 Excellent

The room was very comfortable and clean. Checking in was a breeze. The kitchenette is perfect for cooking and just enough space for two people. The bed was comfortable. The bathroom was very clean. Very home-like feeling. The room was a very nice stroll away from Siesta Key beach which is so lovely. There is a heated pool which was very nice when it was windy outside. All in all, it is a great place to stay for a relaxing time. Small grocery, restaurant and bar all in walking distance.

Monique

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

Carlisle Inn

Pinecraft

10/10 Excellent

Rebecca

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

Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

10/10 Excellent

LAURA

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

Hampton Inn & Suites Venice Bayside South Sarasota

Gateway

10/10 Excellent

Martha

A spacious indoor area with wooden tables and chairs, large windows, and hanging plants.

Kompose Boutique Hotel

Sarasota

10/10 Excellent

Steven

A clear turquoise sea with people swimming and a boat in the distance.

Siesta Palms By the Beach

South Village

10/10 Excellent

We stayed at Siesta by the Palms for one week in June. We were met by Mary Ann, who could not have been any more pleasant and welcoming. Our condo was absolutely beautiful, the kitchen was stocked with dishes, utensils and a welcome bottle of wine, the bed was very comfortable, the lanai overlooked the beautiful pool and sitting area. Our towels were replenished every day. The beach was a very short walk away, which was very convenient for my morning walks & runs and seashell hunting. It was...

Connie

A beach with white lounge chairs and striped umbrellas.

Casey Key Resorts - Beachfront

Casey Key

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors to Osprey speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

What are some of the best vacation rentals in Osprey?

Tropical Villas of Venice Beach: This vacation home rental near Osprey is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Osprey?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Turtle Beach and Nokomis Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. While in the area, you can also visit popular places like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.

Osprey Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osprey vacation rentals

1. Charming Osprey Home

2. Sunny Coastal Escape

3. Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

4. Charming Secluded Tented Cabin in Sarasota, Florida

5. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

6. Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

7. Tropical Beach Resorts

8. A Beach Retreat

9. Hibiscus Suites - Gateway to Siesta Key

10. Tiny House Siesta

11. Captiva Beach Resort

12. Oceanfront home

13. Casey Key Resort

14. SeaSpray Resort

15. The Dolphin

16. 2 Miles to Siesta Key

17. Bright & Beachy–Beach Club Siesta Key 100A by RVA

18. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

19. Casey Key Beachfront Escape: Charming 1BR Cottage

20. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Osprey?

What are some of the best vacation rentals in Osprey?

How many vacation rentals are there in Osprey?

What’s there to see and do in Osprey?

What’s a vacation rental in Osprey like?