Osprey Vacation Rentals from AED 503: Search Short-Term Rentals

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

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

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Our top choices for Osprey vacation rentals

1. Tropical Beach Resorts

South Village

Airida

AED 657 total

includes taxes & fees

7 Sep - 8 Sep

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

2. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Justine

AED 503 total

includes taxes & fees

9 Aug - 10 Aug

Beachside One Bedroom Suite | Premium bedding, pillowtop beds, iron/ironing board (on request)

3. A Beach Retreat

Casey Key

Bob

AED 765 total

includes taxes & fees

27 Aug - 28 Aug

Superior Suite, 2 Bedrooms | In-room safe, iron/ironing board, WiFi (free)

4. SeaSpray Resort

Siesta Key

Isabel

AED 838 total

includes taxes & fees

1 Sep - 2 Sep

5. Captiva Beach Resort

South Village

Vania

AED 693 total

includes taxes & fees

9 Aug - 10 Aug

House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

6. Siesta Heron Suites & Villas

Siesta Key

Christopher Robert

AED 1,233 total

includes taxes & fees

10 Aug - 11 Aug

Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

7. Tiny House Siesta

Sarasota

Mario

AED 836 total

includes taxes & fees

12 Aug - 13 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

AED 1,079 total

includes taxes & fees

9 Aug - 10 Aug

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

Sarasota

AED 1,017 total

includes taxes & fees

9 Aug - 10 Aug

10. Casey Key Resort

Casey Key

Tracie Costello

AED 763 total

includes taxes & fees

3 Sep - 4 Sep

Condo (Beach Club Modern Condo C Building) | Exterior

11. Beach Club Modern Condo C Bldg

South Village

AED 2,113 total

includes taxes & fees

19 Aug - 20 Aug

12. Siesta Key Island Rentals

Siesta Key

Jason

AED 1,474 total

includes taxes & fees

10 Aug - 11 Aug

13. Siesta Heron 6 / Sunset

Siesta Key

AED 2,638 total

includes taxes & fees

1 Sep - 2 Sep

14. Palm Haven at Cape Leyte

Siesta Key

AED 2,400 total

includes taxes & fees

10 Aug - 11 Aug

15. Coastal Home w Hot Tub Firepit and Music Lounge

Siesta Key

AED 2,571 total

includes taxes & fees

10 Aug - 11 Aug

Outdoor pool, pool umbrellas, sun loungers

16. Cedar Run Resort - Roam Hospitality

South Bradenton

Jose Luis Alberti

AED 2,281 total

includes taxes & fees

9 Aug - 10 Aug

17. Gulf View Condominiums

Manasota Key

AED 3,420 total

includes taxes & fees

8 Aug - 9 Aug

18. Sarasota Family Home Private Heated Pool Relax

Whitfield Estates

AED 1,870 total

includes taxes & fees

10 Aug - 11 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

AED 1,777 total

includes taxes & fees

9 Aug - 10 Aug

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Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"Staff"

Siesta Key Beach Resort and Suites

10/10 Excellent

"We had an amazing stay! We came from the east coast of Florida and our friends from Texas flew in and met us there. Between us all we rented four rooms over looking the lounge. The rooms were beautiful and comfortable. The staff was amazing! Estephanie was extremely helpful and accommodating and Joey in the lounge was great at taking care of our party of seven every day. We will definitely be back!"

Carlisle Inn

10/10 Excellent

"Everything was exceptional. It is our second time visiting and it did not disappoint. Thank you for everything. The property is always clean inside and out. They have their own buffet restaurant which is amazingly delicious. The pool is cool even though we couldn’t enjoy it this time around. The breakfast buffet is also delicious with different variations. Staff are amazing thank you all again. My family were very happy to have stayed again. Hopefully we will see you soon."

Aloft by Marriott Sarasota

10/10 Excellent

"Our breakfast was included for an additional fee, I will say that it will make a difference to serve a bigger portion of fruit 4oz cup instead of 2oz or add a fruit bar or a parfait yogurt bar. The portion is small, for me was ok, but for my 15 year old son or husband was a small portion."

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 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 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 vacation rentals in Osprey?

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

How many vacation rentals are there in Osprey?

With 14 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?

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 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.

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Check prices for these dates

Our top choices for Osprey vacation 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

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 vacation rentals that suit your style

Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Casey Key Resorts - Mainland

Siesta Key Beach Resort and Suites

Carlisle Inn

Aloft by Marriott Sarasota

Zota Beach Resort

The Westin Sarasota

Inn at the Beach

The Ritz-Carlton, Sarasota

Frequently asked questions

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