Osprey Vacation Rentals from AED 458: Search Short-Term 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.

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Our top choices for Osprey vacation rentals

1. Charming Secluded Tented Cabin in Sarasota, Florida

Sarasota

AED 1,345 total

includes taxes & fees

23 Sep - 24 Sep

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

Sarasota

AED 1,345 total

includes taxes & fees

23 Sep - 24 Sep

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

Sarasota

AED 1,345 total

includes taxes & fees

23 Sep - 24 Sep

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

Sarasota

AED 1,345 total

includes taxes & fees

23 Sep - 24 Sep

5. Tropical Beach Resorts

South Village

Alexander

AED 656 total

includes taxes & fees

27 Sep - 28 Sep

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

6. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

AED 458 total

includes taxes & fees

28 Sep - 29 Sep

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

7. Tiny House Siesta

Sarasota

Mario

AED 764 total

includes taxes & fees

4 Oct - 5 Oct

8. Captiva Beach Resort

South Village

Karla

AED 704 total

includes taxes & fees

23 Sep - 24 Sep

9. Siesta Key Island Rentals

Siesta Key

Meghan

AED 1,195 total

includes taxes & fees

24 Sep - 25 Sep

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

10. A Beach Retreat

Casey Key

Genghis

AED 765 total

includes taxes & fees

23 Sep - 24 Sep

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

11. SeaSpray Resort

Siesta Key

Michelle Suzanne

AED 902 total

includes taxes & fees

23 Sep - 24 Sep

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

South Village

Cindy F.

AED 1,215 total

includes taxes & fees

23 Sep - 24 Sep

13. Siesta Key, Sea Horse Villa, Pool. Daily rentals

South Village

Allie A.

AED 975 total

includes taxes & fees

23 Sep - 24 Sep

14. Siesta beach....one and only

Sarasota

Jennifer M.

AED 1,716 total

includes taxes & fees

23 Sep - 24 Sep

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

South Village

maureen p.

AED 975 total

includes taxes & fees

23 Sep - 24 Sep

16. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

South Village

Erica B.

AED 1,250 total

includes taxes & fees

23 Sep - 24 Sep

Beach nearby, sun loungers, beach towels

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

Siesta Key Village

Brad S.

AED 1,405 total

includes taxes & fees

23 Sep - 24 Sep

18. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key

K B.

AED 1,978 total

includes taxes & fees

27 Sep - 28 Sep

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

South Village

Evan C.

AED 1,250 total

includes taxes & fees

23 Sep - 24 Sep

20. Beachside Studio Located Across from Main Beach and Half Mile to Village

Sarasota

Karen G.

AED 936 total

includes taxes & fees

23 Sep - 24 Sep

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Top Osprey Hotel Reviews

Tropical Beach Resorts

8/10 Good

"A great place to stay. Right next to the beach! The room was very clean, with fridge, micro, and even an oven. The blinds did not shut all the way, but still gave us privacy, and the door chain was missing the latch - this was not a real concern, but wanted to let staff know. Overall, this place is awesome, and we will definitely book again."

Kompose Boutique Hotel

10/10 Excellent

"We had a great experience. This is the cutest decorated hotel. The staff was very helpful. The pool was clean. The patio was a nice place to Unwind before bed. The breakfast was good. The dining area was fun with whimsical decor. If you're into social media stories there were lots of fun backdrops for content. The staff were very kid friendly. I hope to return or stay at another of their locations. We were minutes from the 4 beautiful beaches we were planning to visit. Loved it. KiKi at the front desk was wonderful."

Tropical Breeze Resort

10/10 Excellent

"We had such an amazing stay at Tropical Cottages! I could not recommend this place enough and definitely see this becoming a regular vacation spot for our family. First off, the location could not be any better. You are literally steps away from the beach and a ton of restaurants! We had our 1 1/2 year old and carried him everywhere, so it was perfect to not have to wander too far to find what we needed. The beach here is UNBELIEVABLE. We grew up in South Florida and have been to several beaches throughout the state. This is 100% my favorite! The rooms were clean, comfy, and cozy. My only complaint (gotta have at least one!) is I wish there were hoses or showers outside the rooms so we could get the sand off our feet before going inside. Such a minor complaint. Everything was just so perfect about our stay and we cannot wait to return! Cannot recommend enough!!"

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent

"Perfect location for our travel baseball team for the weekend. Close enough to the multiple locations we played at and near many different food options. The staff was nice and inviting. Breakfast was good and the hotel itself was well maintained."

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 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?

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.

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Check prices for these dates

Our top choices for Osprey vacation rentals

1. Charming Secluded Tented Cabin in Sarasota, Florida

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

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

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

5. Tropical Beach Resorts

6. Hibiscus Suites - Gateway to Siesta Key

7. Tiny House Siesta

8. Captiva Beach Resort

9. Siesta Key Island Rentals

10. A Beach Retreat

11. SeaSpray Resort

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

13. Siesta Key, Sea Horse Villa, Pool. Daily rentals

14. Siesta beach....one and only

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

16. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

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

18. Casey Key Beachfront Escape: Charming 1BR Cottage

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

20. Beachside Studio Located Across from Main Beach and Half Mile to Village

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

Tropical Beach Resorts

Carlisle Inn

Kompose Boutique Hotel

Spark by Hilton Sarasota Siesta Key Gateway

Tropical Breeze Resort

DoubleTree by Hilton Sarasota Bradenton Airport

Siesta Key Beach Resort and Suites

Embassy Suites by Hilton Sarasota, FL

Golden Host Resort - Sarasota

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