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Osprey Villas

More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers

Flexibility matters
Free cancellation on select hotels and 24/7 support, so you can book with confidence

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Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^

Featured Villas in Osprey

Estimated price for 1 night / 2 adults
Paradise Cove at Lemon Bay
Paradise Cove at Lemon Bay
3.5 out of 5
664 S McCall Rd, Englewood, FL
The price is AU$284 per night

Paradise Cove at Lemon Bay: Pet-friendly villa with free WiFi and free parking. Located near the bay.

No reviews
Paradise Cove at Lemon Bay
Whispering Lake House, Heated Pool, Wi-Fi, Lakeview, Waterfornt
Whispering Lake House, Heated Pool, Wi-Fi, Lakeview, Waterfornt
Venice, FL

This family-friendly Venice villa is located on the waterfront, within 3 mi (5 km) of Jacaranda West Country Club, Caspersen Beach and Woodmere Park. Pelican ...

No reviews
Whispering Lake House, Heated Pool, Wi-Fi, Lakeview, Waterfornt
Seashell Chateau by Beachside Management
Seashell Chateau by Beachside Management
3.5 out of 5
124 Columbus Blvd Apt 9, Siesta Key, FL

Seashell Chateau by Beachside Management: Villa with free WiFi and free parking. Guests love the quiet location!

No reviews
Seashell Chateau by Beachside Management
#1 Beach in US! Peaceful and Tranquil 2 Bedroom Condo Available!
#1 Beach in US! Peaceful and Tranquil 2 Bedroom Condo Available!
5830 Midnight Pass Rd, Siesta Key, FL

#1 Beach in US! Peaceful and Tranquil 2 Bedroom Condo Available!: Romantic villa with an outdoor pool and WiFi. Located by the ocean.

No reviews
#1 Beach in US! Peaceful and Tranquil 2 Bedroom Condo Available!
High-season Special!!! 2/2 Villa ON Sale!!!2 BR, 2 BA, Heated Pool and Jacuzzi!!
High-season Special!!! 2/2 Villa ON Sale!!!2 BR, 2 BA, Heated Pool and Jacuzzi!!
3635 Village des Pins, Palmer Ranch, Sarasota, FL
The price is AU$459 per night

Summer-season Special!!! 2/2 Villa ON Sale! 2 BR, 2 BA, Heated Pool and Jacuzzi!: Romantic resort with an outdoor pool and a hot tub. Located by the sea.

No reviews
High-season Special!!! 2/2 Villa ON Sale!!!2 BR, 2 BA, Heated Pool and Jacuzzi!!
411 Shore Rd - .5mi Walk to Nokomis Beach - Wi-Fi,  HDTV, Amenities Pet Friendly
411 Shore Rd - .5mi Walk to Nokomis Beach - Wi-Fi, HDTV, Amenities Pet Friendly
411 Shore Road, Nokomis, FL

411 Shore Rd - .5mi Walk to Nokomis Beach - Wi-fi, Hdtv, Amenities Pet Friendly: Family villa with WiFi and parking. Located by the ocean.

No reviews
411 Shore Rd - .5mi Walk to Nokomis Beach - Wi-Fi, HDTV, Amenities Pet Friendly
Heated Pool, Beach and Amenities, 2-3 min Walk
Heated Pool, Beach and Amenities, 2-3 min Walk
Siesta Key, FL

Heated Pool, Beach and Amenities, 2-3 min Walk: Villa with 1 bathroom and 2 bedrooms.

No reviews
Heated Pool, Beach and Amenities, 2-3 min Walk
Beautiful 2/2 Villas, Lake-view, King Bed, Wood-floor!! Heated Pool and Jacuzzi!
Beautiful 2/2 Villas, Lake-view, King Bed, Wood-floor!! Heated Pool and Jacuzzi!
3635 White, Yellow Pine Ct, Sarasota, FL
The price is AU$431 per night

Beautiful 2/2 Villas, Lake-view, King Bed, Wood-floor!! Heated Pool and Jacuzzi!: Romantic villa with a hot tub and a fitness centre. Guests give the quiet location ...

No reviews
Beautiful 2/2 Villas, Lake-view, King Bed, Wood-floor!! Heated Pool and Jacuzzi!
403 Shore Rd - Spacious, Walk to Nokomis Beach/Casey Key, Wi-Fi, Pet Friendly
403 Shore Rd - Spacious, Walk to Nokomis Beach/Casey Key, Wi-Fi, Pet Friendly
403 Shore Road, Nokomis, FL

403 Shore Rd - Spacious, Walk to Nokomis Beach/casey Key, Wi-fi, Pet Friendly: Pet-friendly villa with parking and a garden. Located by the ocean.

No reviews
403 Shore Rd - Spacious, Walk to Nokomis Beach/Casey Key, Wi-Fi, Pet Friendly
409 Shore Rd - King Bed, 1/2 Mile Walk to Nokomis Beach, Pet Friendly, Wi-fi
409 Shore Rd - King Bed, 1/2 Mile Walk to Nokomis Beach, Pet Friendly, Wi-fi
409 Shore Road, Nokomis, FL

409 Shore Rd - King Bed, 1/2 Mile Walk to Nokomis Beach, Pet Friendly, Wi-fi: Family villa with WiFi and parking. Located by the ocean.

No reviews
409 Shore Rd - King Bed, 1/2 Mile Walk to Nokomis Beach, Pet Friendly, Wi-fi
Sensational Waterviews Suite-walk to Beach! Travel Flexibility&enhanced Cleaning
Sensational Waterviews Suite-walk to Beach! Travel Flexibility&enhanced Cleaning
Englewood, FL

Sensational Waterviews Suite-walk to Beach! Travel Flexibility&enhanced Cleaning: Romantic resort with an outdoor pool and WiFi. Located by the sea.

No reviews
Sensational Waterviews Suite-walk to Beach! Travel Flexibility&enhanced Cleaning
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly
Englewood, FL

Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-friendly: Family villa with private pools and WiFi. Guests love the pool!

No reviews
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly

Private & Luxury Villas in Osprey

For your next batch of annual leave, holiday in style in one of our private villas in Osprey. All you need, friend, is a reason to go and Wotif to help you get there.

Osprey villa holidays are especially popular with families, large groups, couples…wait, that’s just about everyone. It’s easy to see why: Villas allow you plenty of space to spread out and do your thing, whether you’ve got ten people or two. Planning for a wedding, and need to make sure Grandma, Aunt Liz, and your second cousin aren’t all on top of each other? A villa has you covered. Going on a romantic couple’s getaway, and just want to feel like you have a whole, secluded paradise to yourselves? Osprey villas were basically made for that.

The phrase “luxury villa” may seem redundant, because pretty much all Osprey villas are luxurious. But when you add that extra word, a whole new world opens up to you. Incomparable service, extra amenities, and features like pools, steam rooms, gyms, and even in-room massage are all on the menu when you step up the star rating. But no matter your price range, you’ll find what you need right here on Wotif. We have to warn you, though, you may not want to browse while you’re at work. You’re liable to start daydreaming so hard, you’ll miss your next meeting.

Top Trending Hotels in Osprey

Estimated price for 1 night / 2 adults
Bentley's Boutique Hotel, BW Premier Collection
Bentley's Boutique Hotel, BW Premier Collection
3.5 out of 5
1660 South Tamiami Trail, Osprey, FL
The price is AU$110 per night

Situated in the historical district, this resort is 0.3 mi (0.5 km) from Oscar Scherer State Park, and within 3 mi (5 km) of Turtle Beach and Nokomis Beach. ...

5/5Exceptional! (1 review)
Bentley's Boutique Hotel, BW Premier Collection
Virage Hotel
Virage Hotel
3 out of 5
1650 South Tamiami Trail, Osprey, FL
The price is AU$122 per night

Situated in Osprey, this hotel is 0.3 mi (0.6 km) from Oscar Scherer State Park and within 3 miles (5 km) of Turtle Beach and Nokomis Beach. Historic Spanish ...

No reviews
Virage Hotel
337 COMFY  COZY PLACE
337 COMFY COZY PLACE
337 Bay Vista Ave, Osprey, FL
The price is AU$232 per night

Located in Bay Acres, this holiday home is 0.9 mi (1.5 km) from Historic Spanish Point and within 3 miles (5 km) of Turtle Beach and Nokomis Beach. Oscar Scherer ...

No reviews
337 COMFY COZY PLACE

Travel to Osprey & explore

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