Osprey Vacation Rentals from AED 461: 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

Charming cottage for 2 across warm mineral springs park

Warm Mineral Springs

Robert J.

AED 509 total

includes taxes & fees

23 Jun - 24 Jun

Path to Paradise.

Olde Englewood Village

Jeremy

AED 955 total

includes taxes & fees

29 Jun - 30 Jun

Kon Tiki Inn

Venice Island

Tara

AED 461 total

includes taxes & fees

30 Jun - 1 Jul

Mimosa Memories

South Venice

Susan H.

AED 1,211 total

includes taxes & fees

23 Jun - 24 Jun

Chadwick Cove Resort & Marina

Manasota Key

isabel

AED 2,052 total

includes taxes & fees

7 Jul - 8 Jul

Waterfront Condo Walkable to Everything with Beach Access

Manasota Key

Jennifer J.

AED 1,641 total

includes taxes & fees

23 Jun - 24 Jun

Beautiful University Pines Studio in Sarasota

Sarasota

Maria B.

AED 750 total

includes taxes & fees

23 Jun - 24 Jun

Siesta Key Island Rentals

Siesta Key

Alessandra

AED 1,290 total

includes taxes & fees

24 Jun - 25 Jun

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Top Osprey Hotel Reviews

Lantern Inn & Suites

10/10 Excellent

"La habitación estaba super limpia,la ropa de cama,las toallas,baño y cocina en perfecto estado y muy higiénico todo.Un ambiente tranquilo.La atención fué muy buena,al final nos devolvieron los $ 150 del depósito.Solo estuvimos 1 día con su noche.No utilizamos la piscina y el bar.La relación calidad--precio es justa.Sin dudas la recomendaría y si volvemos a Sarasota nuevamente,volveríamos a quedarnos allí.Felicitaciones!"

Tropical Breeze Resort

8/10 Good

"This resort is very close to the beach, bars, restaurants and shopping. You can literally walk to everything. The room was very nice the only thing is you don’t get daily cleaning and need to request more towels. The people cleaning the rooms were very nice and hardworking though. Check in was not great as I had to wait nearly 45 minutes before my room was ready. The lady at the front desk was very nice and made she communicated well. Overall I enjoyed my stay and will stay again."

Carlisle Inn

10/10 Excellent

"I cannot recommend the Carlisle Inn Sarasota highly enough. From check-in to check-out, every staff member was genuinely warm, welcoming, and professional. They were always smiling, saying hello, and making sure guests had everything they needed. Their hospitality made the hotel feel family-run. This is, without question, the cleanest hotel I’ve ever stayed in. Spotless is an understatement. Every hallway, common area, and guest room was immaculate. Everything looked brand new, and I even saw a staff member touching up a wall with fresh paint. It’s obvious they take great pride in maintaining the property. The complimentary cookies served every evening were a delicious bonus. My king room was exceptionally well designed. The bathroom was separate from a large walk-in closet that included a second vanity and sink for getting ready. The closet also had a pocket door, creating a private dressing area. It’s a brilliant layout—one person can use the bathroom, another can get dressed in the bedroom, and another can get ready in the closet at the same time. The location was perfect—about 10–15 minutes from St. Armands Circle and a short drive to beaches, restaurants, and everything else we wanted to visit. The hotel felt quiet, safe, and exceptionally well cared for. I would absolutely stay here again and recommend it to anyone visiting Sarasota."

Embassy Suites by Hilton Sarasota, FL

8/10 Good

"Nice room, bar and wait staff excellent. Hotel was hosting families for a junior soccer tournament resulting in overcrowded pool area and coupled with one non operational elevator resulted in abnormally long waits for movement around facility. Kids were unattended by parents in pool and around facility playing with operational elevators. Parents were not chaperoning kids and hotel staff did not intervene and enforce posted rules. We have stayed here on numerous occasions and facility is normally first rate. My bad for not doing due diligence and checking if facility was hosting special event. Will definitely do it next time. Also thought $40 per day self parking fee was excessive"

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 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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Our top choices for Osprey vacation rentals

Charming cottage for 2 across warm mineral springs park

Path to Paradise.

Kon Tiki Inn

Mimosa Memories

Chadwick Cove Resort & Marina

Waterfront Condo Walkable to Everything with Beach Access

Beautiful University Pines Studio in Sarasota

Siesta Key Island Rentals

Very tropical, private and peaceful, short walk to everything happening downtown

Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.

Lavish Lakeview Condo · Two Pools · Near IMG · Anna Maria Island · Restaurants

Two Miles to Siesta Key

Cozy Corner Condo · Two Pools & Hot Tubs · IMG · Anna Maria Island · Restaurants

[escape to paradise] siesta key beach getaway

Siesta Key Village-Suite #3: A Block to the Beach!

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Paradise Retreat with HEATED POOL-- Need We Say More

Lakeview Corner Condo · Two Pools · Near IMG · Anna Maria Island · Restaurants

Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants

Step from the Beach.Renovated ground Floor unit 63

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

Lantern Inn & Suites

Kompose Boutique Hotel

Tropical Breeze Resort

Tropical Beach Resorts

Comfort Suites Sarasota - Siesta Key

Carlisle Inn

Embassy Suites by Hilton Sarasota, FL

Golden Host Resort - Sarasota

Spark by Hilton Sarasota Siesta Key Gateway

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