Osprey Vacation Rentals from ￥16,925: 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 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. Charming Osprey Home

Bay Acres

Diane S.

￥62,888 total

includes taxes & fees

Aug 27 - Aug 28

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

Sarasota

￥56,286 total

includes taxes & fees

Aug 27 - Aug 28

3. Charming Secluded Tented Cabin in Sarasota, Florida

Sarasota

￥56,286 total

includes taxes & fees

Aug 27 - Aug 28

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

Sarasota

￥56,286 total

includes taxes & fees

Aug 27 - Aug 28

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

Sarasota

￥56,286 total

includes taxes & fees

Aug 27 - Aug 28

6. Tropical Beach Resorts

South Village

Margaret Lai Ling

￥24,126 total

includes taxes & fees

Aug 27 - Aug 28

Cabin (Tiny House - The Siesta) | Living area

7. Tiny House Siesta

Sarasota

Mario

￥36,680 total

includes taxes & fees

Sep 9 - Sep 10

8. Siesta Key Island Rentals

Siesta Key

Jason

￥52,207 total

includes taxes & fees

Aug 27 - Aug 28

9. Tropical Villas of Venice Beach

Venice Island

Christina

￥16,925 total

includes taxes & fees

Aug 27 - Aug 28

10. Captiva Beach Resort

South Village

natalia

￥29,749 total

includes taxes & fees

Sep 10 - Sep 11

11. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

￥21,814 total

includes taxes & fees

Sep 1 - Sep 2

12. A Beach Retreat

Casey Key

Robert

￥33,128 total

includes taxes & fees

Aug 27 - Aug 28

13. [escape to paradise] siesta key beach getaway

Siesta Key

"We appreciated the excellent location and good service. However, the listing should provide clearer and more accurate information about the layout, especially that the only bathroom is located inside one of the bedrooms. This arrangement significantly reduces privacy and makes the two-bedroom setup less convenient than expected. The additional $40-per-person bicycle fee should also be clearly stated in the listing."

Tatyana

￥51,139 total

includes taxes & fees

Aug 30 - Aug 31

14. SeaSpray Resort

Siesta Key

Isabel

￥34,110 total

includes taxes & fees

Sep 1 - Sep 2

15. 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

￥53,458 total

includes taxes & fees

Aug 27 - Aug 28

16. [lounge like locals] walk to siesta beach +bikes

Siesta Key

Sue H.

￥53,736 total

includes taxes & fees

Sep 2 - Sep 3

17. Dolphin Villa - Pool - Steps to Siesta Key Village

Siesta Key Village

"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "

Sandra C.

￥58,633 total

includes taxes & fees

Sep 3 - Sep 4

18. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

South Village

Cindy F.

￥55,190 total

includes taxes & fees

Aug 27 - Aug 28

19. Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village

Brad S.

￥61,451 total

includes taxes & fees

Aug 30 - Aug 31

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

South Village

maureen p.

￥53,671 total

includes taxes & fees

Aug 27 - Aug 28

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Top Osprey Hotel Reviews

Kompose Boutique Hotel

8/10 Good

"It’s nice"

Carlisle Inn

10/10 Excellent

"We had a wonderful time at this hotel. The bed and pillows were Marriot quality and great, the breakfast was wonderful. They also had cookies every day from 4-9 pm and hot chocolate. The room looked updated and very clean. AC worked perfectly. No dust anywhere. The best part was the front desk workers. They were always so kind and willing to walk the extra mile to please us. We will use this hotel more often from now on. The Lido Beach was 15 minutes away, and Siesta Keys was 20-25 minutes away. We chose this hotel because it was a good price and it had all if the amenities that we were looking for. No room safe, but we used their safe boxes at the front desk without a problem. One extra perk was the ability to borrow towels, chairs, and umbrela for the beach free of cost. Parking was also plenty at the hotel. We also recommend Libby Restaurant close to Siesta Key. Amazing food at a great price. The shrimp pasta with butter sauce was outstanding and they even gifted us with a chocolate pie that was wonderful."

Find out more about Osprey

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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?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with 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 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?

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 Venice 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. Charming Osprey Home

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

3. Charming Secluded Tented Cabin in Sarasota, Florida

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

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

6. Tropical Beach Resorts

7. Tiny House Siesta

8. Siesta Key Island Rentals

9. Tropical Villas of Venice Beach

10. Captiva Beach Resort

11. Hibiscus Suites - Gateway to Siesta Key

12. A Beach Retreat

13. [escape to paradise] siesta key beach getaway

14. SeaSpray Resort

15. The Inn On Siesta Key

16. [lounge like locals] walk to siesta beach +bikes

17. Dolphin Villa - Pool - Steps to Siesta Key Village

18. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

19. Siesta Key Village-Suite #1: A block to the Beach!

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

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

Kompose Boutique Hotel

Siesta Key Palms Resort

Tropical Beach Resorts

Carlisle Inn

DoubleTree by Hilton Sarasota Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

Siesta Key Beach Resort and Suites

Lido Beach Resort

The Ritz-Carlton, Sarasota

Find out more about Osprey

Frequently asked questions

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