Osprey Short-Term Rentals from S$182: Search Holiday Rentals

Q: What are some of the best holiday rentals that Osprey has to offer?

Siesta Key Island Rentals : This holiday home rental outside of Osprey comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

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Our top choices for Osprey holiday rentals

1. Tropical Beach Resorts

South Village

Airida

includes taxes & fees

25 Aug - 26 Aug

Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

2. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Justine

includes taxes & fees

19 Aug - 20 Aug

Premium bedding, pillow-top beds, iron/ironing board (on request)

3. A Beach Retreat

Casey Key

Bob

includes taxes & fees

27 Aug - 28 Aug

In-room safe, iron/ironing board, free WiFi

4. SeaSpray Resort

Siesta Key

Isabel

includes taxes & fees

1 Sept - 2 Sept

5. Captiva Beach Resort

South Village

Vania

includes taxes & fees

9 Aug - 10 Aug

6. Siesta Heron Suites & Villas

Siesta Key

Christopher Robert

includes taxes & fees

12 Aug - 13 Aug

7. Tiny House Siesta

Sarasota

Mario

includes taxes & fees

23 Aug - 24 Aug

Beach nearby, white sand, beach umbrellas, beach towels

8. The Inn On Siesta Key

Siesta Key

"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...

Lisa

includes taxes & fees

9 Aug - 10 Aug

9. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Sarasota

includes taxes & fees

9 Aug - 10 Aug

10. Casey Key Resort - Gulf Shores

Casey Key

Tracie Costello

includes taxes & fees

1 Sept - 2 Sept

11. Beach Club Modern Condo C Bldg

South Village

includes taxes & fees

19 Aug - 20 Aug

12. Siesta Key Island Rentals

Siesta Key

Jason

includes taxes & fees

10 Aug - 11 Aug

13. Siesta Heron 6 / Sunset

Siesta Key

includes taxes & fees

1 Sept - 2 Sept

14. Palm Haven at Cape Leyte

Siesta Key

includes taxes & fees

10 Aug - 11 Aug

15. Coastal Home w Hot Tub Firepit and Music Lounge

Siesta Key

includes taxes & fees

10 Aug - 11 Aug

Outdoor pool, pool umbrellas, pool loungers

16. Cedar Run Resort - Roam Hospitality

South Bradenton

Jose Luis Alberti

includes taxes & fees

9 Aug - 10 Aug

17. Gulf View Condominiums

Manasota Key

includes taxes & fees

8 Aug - 9 Aug

18. Sarasota Family Home Private Heated Pool Relax

Whitfield Estates

includes taxes & fees

9 Aug - 10 Aug

19. Unwind Poolside + Walk to Beach! Sarasota Retreat

South Village

"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "

Eleuterio

20. FANCY RETREREAT

Bradenton

includes taxes & fees

9 Aug - 10 Aug

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Top Osprey Hotel Reviews

Golden Host Resort - Sarasota

10/10 Excellent

"Nice clean motel. Everything you need. Some noise from the road. Ask for a pool view room."

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"We loved our stay. The hotel is only less than 10min drive to the beach The pool with a bar was a big plus for us, after 3 hours driving! Lol The hotel is clean, the breakfast is nothing too much but was good - I missed cheese, ham, bacon and milk, for example, but it wasn't a big deal. The room is very clean, but the curtains didn't covers the windows very well and for me (light sleeper) the room wasn't dark enough and I had some trouble to sleep, ai had to put a face towel on my face to be able to sleep... The shower is very weak and this was a head ache to wash my hair (I have a big and lot of hair!). And, the room didn't have a microwave or soap at the sink - didn't understand why! Overall, is worth the money and it is a good stay."

The Ritz-Carlton, Sarasota

10/10 Excellent

"Our stay at The Ritz-Carlton Sarasota was absolutely amazing! From the moment we arrived, the staff made us feel welcome with their exceptional hospitality and attention to detail. Everyone was friendly, professional, and went above and beyond to ensure our stay was perfect. The hotel was spotless, with beautifully maintained spaces that made the stay even more relaxing and enjoyable. The food was delicious, with excellent quality, presentation, and flavor at every meal. We highly recommend Jack Dusty. Overall, it was an unforgettable experience, and I highly recommend The Ritz-Carlton Sarasota for luxury, comfort, and world-class service. We can’t wait to return!"

Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Osprey speak positively about the popular beaches and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best holiday rentals that Osprey has to offer?

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 14 Expedia holiday rentals, you're guaranteed to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Siesta Key Beach and Lido Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.

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Check prices for these dates

Our top choices for Osprey holiday rentals

1. Tropical Beach Resorts

2. Hibiscus Suites - Gateway to Siesta Key

3. A Beach Retreat

4. SeaSpray Resort

5. Captiva Beach Resort

6. Siesta Heron Suites & Villas

7. Tiny House Siesta

8. The Inn On Siesta Key

9. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

10. Casey Key Resort - Gulf Shores

11. Beach Club Modern Condo C Bldg

12. Siesta Key Island Rentals

13. Siesta Heron 6 / Sunset

14. Palm Haven at Cape Leyte

15. Coastal Home w Hot Tub Firepit and Music Lounge

16. Cedar Run Resort - Roam Hospitality

17. Gulf View Condominiums

18. Sarasota Family Home Private Heated Pool Relax

19. Unwind Poolside + Walk to Beach! Sarasota Retreat

20. FANCY RETREREAT

Find holiday rentals that suit your style

Top Osprey Hotel Reviews

Golden Host Resort - Sarasota

Spark by Hilton Sarasota Siesta Key Gateway

Carlisle Inn

Tropical Beach Resorts

Lido Beach Resort

Inn at the Beach

Kompose Boutique Hotel

The Ritz-Carlton, Sarasota

Zota Beach Resort

Frequently asked questions

Go further with the Expedia app

Osprey Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osprey holiday rentals

1. Tropical Beach Resorts

2. Hibiscus Suites - Gateway to Siesta Key

3. A Beach Retreat

4. SeaSpray Resort

5. Captiva Beach Resort

6. Siesta Heron Suites & Villas

7. Tiny House Siesta

8. The Inn On Siesta Key

9. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

10. Casey Key Resort - Gulf Shores

11. Beach Club Modern Condo C Bldg

12. Siesta Key Island Rentals

13. Siesta Heron 6 / Sunset

14. Palm Haven at Cape Leyte

15. Coastal Home w Hot Tub Firepit and Music Lounge

16. Cedar Run Resort - Roam Hospitality

17. Gulf View Condominiums

18. Sarasota Family Home Private Heated Pool Relax

19. Unwind Poolside + Walk to Beach! Sarasota Retreat

20. FANCY RETREREAT

Find holiday rentals that suit your style

Top Osprey Hotel Reviews

Golden Host Resort - Sarasota

Frequently asked questions

Go further with the Expedia app