Osprey Vacation Rentals from ￥20,348: 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

A tented accommodation with a bed, a small table, and a hanging plant.

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

Sarasota

￥56,148 total

includes taxes & fees

Oct 19 - Oct 20

A grill with a stick over it, a tent, and two chairs in the background.

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

Sarasota

￥56,148 total

includes taxes & fees

Oct 20 - Oct 21

A tent with two chairs and a welcome mat in front.

3. Charming Secluded Tented Cabin in Sarasota, Florida

Sarasota

￥56,148 total

includes taxes & fees

Oct 19 - Oct 20

A tent with a wooden platform, surrounded by trees and gravel.

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

Sarasota

￥56,148 total

includes taxes & fees

Oct 19 - Oct 20

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

5. Tropical Beach Resorts

South Village

Liliana

￥25,998 total

includes taxes & fees

Oct 19 - Oct 20

A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

6. Captiva Beach Resort

South Village

Karla

￥33,224 total

includes taxes & fees

Oct 18 - Oct 19

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.

7. Oceanfront home

Vamo

Ashley H.

￥100,500 total

includes taxes & fees

Oct 28 - Oct 29

A modern living room with a black leather sofa, a glass dining table, and a flat-screen TV mounted on the wall.

8. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

￥20,348 total

includes taxes & fees

Oct 18 - Oct 19

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

9. A Beach Retreat

Casey Key

Robin

￥32,904 total

includes taxes & fees

Nov 4 - Nov 5

A wooden structure with a thatched roof overlooking a beach.

10. Casey Key Resort

Casey Key

jay

￥36,274 total

includes taxes & fees

Oct 28 - Oct 29

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.

11. SeaSpray Resort

Siesta Key

Rommel

￥35,613 total

includes taxes & fees

Nov 16 - Nov 17

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

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

South Village

maureen p.

￥48,049 total

includes taxes & fees

Oct 19 - Oct 20

A beach scene with a large sandcastle and people around it.

13. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

South Village

Clarissa S.

￥47,891 total

includes taxes & fees

Oct 24 - Oct 25

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

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

South Village

Cindy F.

￥52,461 total

includes taxes & fees

Oct 18 - Oct 19

A beach with clear turquoise water and gentle waves.

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

South Village

Allie A.

￥46,261 total

includes taxes & fees

Oct 18 - Oct 19

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

South Village

Evan C.

￥53,956 total

includes taxes & fees

Oct 18 - Oct 19

17. The Inn On Siesta Key

Siesta Key

Stephen

￥49,487 total

includes taxes & fees

Oct 18 - Oct 19

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

South Village

Erica B.

￥56,024 total

includes taxes & fees

Oct 18 - Oct 19

19. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

South Village

Gelsy

￥74,367 total

includes taxes & fees

Oct 18 - Oct 19

A beach path leading to the sea with grass on either side.

20. Jetties Pointe Cottage #5 - 408 “Casey Key”

Casey Key

Evan T.

￥60,564 total

includes taxes & fees

Oct 18 - Oct 19

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Top Osprey Hotel Reviews

Kompose Boutique Hotel

8/10 Good

"I have stayed at this location several times already and I keep returning due to its location and convenience. I did have a minor issue with my room this week, the mirror over the light kept flickering, I told the front staff and they fixed it. When I returned back to my room later, it began to flicker once again. Not a huge deal because it seems like this could be normal wear and tear over time but I appreciate the staff’s promptness is addressing it. There was a water outage this trip due to a main line being cut by construction being done at the airport and the staff seemed to be very patient with customers who seemed to be frustrated about it. There wasn’t anything the hotel could do but provide bottled water in the interim but the issues was resolved some time during the night. I am returning next week and I hope check in will be smooth as I’ve had some odor issues the last 2 late check ins. Other than that, this is a great place to stay if you’re looking for convenience and friendly staff."

Cottages at Siesta Key Inn

10/10 Excellent

"The Cottages were sold to Azul Resorts which has another similar location around the corner. The entire complex went through a renovation in December of 2025. Expedia still shows it under the old name, and that was a little confusing when I arrived. It looked very clean and new for the most part. I booked the Studio unit with a King size bed. The bed was comfortable and the pillows were great. There is a 65" TV on the wall. It was exactly the same as the one I have at home which was great because I didn't have to learn how to work it. :-) The location is about 250 ft. from the beach access entrance (#13), which is another 200 foot walking path to the sand. The path leaves you about 150 feet from the water (low tide), and about 100 feet from the water (high tide). So if walking is difficult for you, know that you will walk approximately 550 feet before you can wet your toes in the Gulf of America. Regarding the location, it is about 4 miles South of the Sarasota Village downtown, 3 miles South of the main Sarasota Beach public parking area, but there are plenty of restaurant and tiki bars within 1 or 2 miles of the Azul Resort. The only cons I found were that the pool wasn't heated, and someone operates a chair and umbrella rental service that blocks a huge part of the beach area. There is room to the left of the path, or you can go to the right of the blocked off area. They also leave a small strip in front of the blocked area. We didn't have a problem finding room on d'sand."

Siesta Key Beach Resort and Suites

8/10 Good

"I had a three night stay at this hotel on Siesta Key. Great location, and I walked every where safely alone. Very friendly staff! My comments on the room. - the mattress needs to be replaced in room 102 - a threshold at the door would be nice to keep any critters from crawling into the room. - the dehumidifier in the room makes some very loud sounds, frequently, which woke me often."

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?

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.

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Check prices for these dates

Our top choices for Osprey vacation rentals

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

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

3. Charming Secluded Tented Cabin in Sarasota, Florida

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

5. Tropical Beach Resorts

6. Captiva Beach Resort

7. Oceanfront home

8. Hibiscus Suites - Gateway to Siesta Key

9. A Beach Retreat

10. Casey Key Resort

11. SeaSpray Resort

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

13. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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

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

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

17. The Inn On Siesta Key

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

19. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

20. Jetties Pointe Cottage #5 - 408 “Casey Key”

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

Kompose Boutique Hotel

The Westin Sarasota

Carlisle Inn

Tropical Breeze Resort

Cirque St. Armands Beachside

Cottages at Siesta Key Inn

Siesta Key Beach Resort and Suites

Find out more about Osprey

Frequently asked questions

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