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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 464 Villas in Osprey with updated reviews, rates, and availability.

Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
Lake

Beach, Sand, Sunsets. . . Rocking chair in front of the porch!

9.8 out of 10, Exceptional, (105)
"We had the greatest little getaway here! The place was clean and stocked with everything we needed, including beach supplies. It was awesome to walk directly onto the beach :) We can’t wait to come back! "
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
Waterfront Villa Seaglass
A heated pool

Waterfront Villa Seaglass

10.0 out of 10, Exceptional, (76)
"Seaglass Villa was a cute little unit that afforded great views of the sunrise each morning. The location was close to the beach & some fun restaurants & vacation options. A really nice winter getaway for those of us from the frigid north. "
Waterfront Villa Seaglass
Waterfront Paradise Bay
A heated pool

Waterfront Paradise Bay

10.0 out of 10, Exceptional, (75)
"We loved our time in this condo. Everything we needed was there. Great communication between owner and us. Wed stay there again."
Waterfront Paradise Bay
Waterfront Mermaid's Retreat Delights!
Aerial view

Waterfront Mermaid's Retreat Delights!

9.8 out of 10, Exceptional, (57)
"We were welcomed by a bottle of wine and the staff! Our accommodations were neat and clean and nicely decorated. We had our own door, parking place and a beach across the street! "
Waterfront Mermaid's Retreat Delights!
Completely Remodeled- 150 Yards to Beach and Restaurants!
Exterior

Completely Remodeled- 150 Yards to Beach and Restaurants!

10.0 out of 10, Exceptional, (28)
"Our family had to split up spring break vacations due to college schedules so I got the unique opportunity to take our two young adult kids to the beach for several days. The location of the duplex is great! It was fun and convenient to be able to walk to all the places in the south village and walk to the gorgeous beach! We had hoped to snorkel at point of rocks which is so close to the beach entrance but the weather didn’t cooperate and was too windy, but if possible this location is perfect...
The price is SAR 1,031
SAR 2,065 total
includes taxes & fees
15 Apr - 16 Apr
Completely Remodeled- 150 Yards to Beach and Restaurants!
Lanai + Community Pool Access: Sarasota Oasis!
Pool

Lanai + Community Pool Access: Sarasota Oasis!

9.6 out of 10, Exceptional, (12)
"Clean, big, LOTS of space. They had a pull out bed in addition to the king, queen, and twin..a pull out crib... towels.. a highchair... the TV had netflix/hulu options... the pool was nice. Neighborhood was nice. Overall amazing experience. 👏"
Lanai + Community Pool Access: Sarasota Oasis!
Direct Beachfront Gulf with Amazing Views
On the beach, sun loungers, beach towels

Direct Beachfront Gulf with Amazing Views

9.8 out of 10, Exceptional, (91)
"The condo is beautifully located on the beach. Great view of the Gulf from balcony. This place is exceptionally clean. "
Direct Beachfront Gulf with Amazing Views
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3
Beach nearby, sun loungers, beach towels

Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3

9.8 out of 10, Exceptional, (92)
"Cozy cottage was everything we were looking for! Close to the beach, the village with restaurants & shops. We rented bikes to explore and at times a little busy on the narrow roads/bridges, was well worth not renting a car. Liked having the beach chairs and towels and wagon for transporting to the beach. Overall wonderful! "
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3
6 BR Heated Pool, Mins from IMG and Anna Maria
Dining

6 BR Heated Pool, Mins from IMG and Anna Maria

3.0 star property
The price is SAR 823
SAR 2,685 total
includes taxes & fees
24 Mar - 25 Mar
6 BR Heated Pool, Mins from IMG and Anna Maria
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
Marina

"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath

10.0 out of 10, Exceptional, (10)
"We had a birthday weekend for our son his family and brother & wife. It was perfect, the house was so well equipped, clean, and great location. Hopefully, we can stay there again!"
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
Beachy 3-bedroom Villa on Siesta Key with WiFi, AC
Fridge, microwave, oven, stovetop

Beachy 3-bedroom Villa on Siesta Key with WiFi, AC

10.0 out of 10, Exceptional, (2)
"This house is clean, beds and showers are top notch quality, all new appliances, great location to access everything on Siesta key, nice walk to beach, quiet, wonderful pool, kind neighbors, responsive host! "
Beachy 3-bedroom Villa on Siesta Key with WiFi, AC
Tropical Oasis Close to Beaches | Pool | Game room
Outdoor dining

Tropical Oasis Close to Beaches | Pool | Game room

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was perfect for 2 families including teens and young adults. With 2 master suites, a game room and large screened in lanai, there was plenty of space for everyone to spread out. The home has been beautifully renovated with the latest finishes. We even hosted our extended family for thanksgiving and there was room to seat 20 comfortably. Highly recommend! "
Tropical Oasis Close to Beaches | Pool | Game room
LUXURIOUS VILLA WATERFRONT NEAR SIESTA KEY BEACH
Pool

LUXURIOUS VILLA WATERFRONT NEAR SIESTA KEY BEACH

LUXURIOUS VILLA WATERFRONT NEAR SIESTA KEY BEACH
Huge Beach Villa, Mins To Beach With Private Salt Water Heated Pool
Interior

Huge Beach Villa, Mins To Beach With Private Salt Water Heated Pool

10.0 out of 10, Exceptional, (2)
"This booking was 5/5 stars in every way! Booking was easy, communication was prompt and thorough, and the home is amazing. Very clean and freshly updated, plentiful necessities, beautiful pool (with a dedicated poolside bathroom and shower) and a master bath with a shower to die for! We loved our week and hated to leave!! Would not hesitate to rent again."
Huge Beach Villa, Mins To Beach With Private Salt Water Heated Pool
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
Fridge, microwave, oven, stovetop

Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

9.4 out of 10, Exceptional, (49)
"Place was great! Clean and all new interior decor, furniture and appliances. Awesome location. Would definitely come back again. "
The price is SAR 544
SAR 1,302 total
includes taxes & fees
10 Apr - 11 Apr
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
Casa Blanca Villa C05
Beach nearby

Casa Blanca Villa C05

9.8 out of 10, Exceptional, (9)
"Great location, friendly, and hospitality. Staff was very helpful and friendly, Jeff bailed us out with a difficulty in the laundry room."
Casa Blanca Villa C05
Renovated 1 Bed / 1 Bath Condo on Siesta Beach!
Pool

Renovated 1 Bed / 1 Bath Condo on Siesta Beach!

10.0 out of 10, Exceptional, (6)
"This place exceeded our expectations! Everything was clean and the furniture was comfortable. The kitchen is perfect with the appliances and the washer dryer a huge plus! The location to the beach and other fun things to do! Communication was great, check in and check out was super easy! Hopefully we will be back again!!"
Renovated 1 Bed / 1 Bath Condo on Siesta Beach!
Casa Blanca Villa D08
Beach nearby

Casa Blanca Villa D08

9.4 out of 10, Exceptional, (16)
"Everything were perfect"
Casa Blanca Villa D08
Venice Island / Venice Beach Luxury Villa
Beach

Venice Island / Venice Beach Luxury Villa

9.4 out of 10, Exceptional, (113)
"The property was in a great location to the beach. The unit was very clean and updated. I would recommend. "
Venice Island / Venice Beach Luxury Villa
Siesta Key Palm Paradise with Heated Saltwater Pool
A heated pool

Siesta Key Palm Paradise with Heated Saltwater Pool

9.8 out of 10, Exceptional, (12)
"Pool was nice"
Siesta Key Palm Paradise with Heated Saltwater Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Osprey

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4592)
"Brandy at front desk is the best. Outstanding service"
The price is SAR 960
SAR 1,169 total
includes taxes & fees
23 Mar - 24 Mar
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2104)
"Near the beach location and welcoming host "
The price is SAR 772
SAR 872 total
includes taxes & fees
1 Apr - 2 Apr
Hibiscus Suites - Gateway to Siesta Key
Tiny House Siesta
Cabin (Tiny House - Yellow Lifeguard Stand) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (236)
"❤️"
The price is SAR 338
SAR 593 total
includes taxes & fees
1 Apr - 2 Apr
Tiny House Siesta
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in Osprey cost?
Villas in Osprey cost between and per night. These getaways provide the privacy to enjoy your own space at a price that won’t stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Osprey?
A guest favorite is Island House Beach Resort V39. Settle in at this 3-star property which offers a barbecue grill and a swimming pool. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is another popular option worth considering. Book into this 2.5-star stay and you’ll have access to conveniences like a barbecue grill and a swimming pool. You can pick from multiple villas in Osprey with a total average guest review rating of 9.8.
How many villas are there in Osprey?
Take your pick of 464 villas in Osprey. No matter if you’re vacationing with the family or getting away with some friends, Expedia will help you find the best space for your whole crew.
Why book your villa in Osprey with Expedia?
Expedia makes it a cinch to find your dream villa in Osprey. Getting away with the family? Make the most of our filters to search for stays with amenities like WiFi and a pool. If you need to stick to a budget, choose how much you’re willing to spend and the star rating of the property. We’ll help you find a perfect place that matches your style and taste.
How can I find cheap villas in Osprey?
The quickest way to zero in on cheap villas in Osprey is with Expedia’s handy filter tool. Tailor your search results by amenities, budget and star rating to nab unbeatable prices in just a couple of clicks.