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Great deal
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Beach access
Sand Dollar Retreat
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun loungers
Providing guests with a terrace and a picnic area to ensure a memorable stay, the 2-bedroom Sand Dollar Retreat Osprey villa is nearly a 5-minute walk from Historic Spanish Point. Located 3.6 km from Oscar Scherer State Park, the property provides Wi-Fi and private parking.
Sand Dollar Retreat
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun loungers
Sand Dollar Retreat
Providing guests with a terrace and a picnic area to ensure a memorable stay, the 2-bedroom Sand Dollar Retreat Osprey villa is nearly a 5-minute walk from Historic Spanish Point. Located 3.6 km from Oscar Scherer State Park, the property provides Wi-Fi and private parking.
Sarasota Home With Pool
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Car park
Charges may apply
- Air conditioning
- Ironing facilities
- Indoor swimming pool
The 3-bedroom Sarasota Home With Pool Osprey is nestled just 1.4 km from Historic Spanish Point and provides an indoor pool.
Sarasota Home With Pool
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Car park
Charges may apply
- Air conditioning
- Ironing facilities
- Indoor swimming pool
Sarasota Home With Pool
The 3-bedroom Sarasota Home With Pool Osprey is nestled just 1.4 km from Historic Spanish Point and provides an indoor pool.
Coastal Osprey Retreat With Dock, Pool & Water Views
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
- Patio
The 5-bedroom Coastal Osprey Retreat With Dock, Pool & Water Views Villa offers proximity to nearby tourist spots, such as Oscar Scherer State Park, situated around 10 minutes away by car.
Coastal Osprey Retreat With Dock, Pool & Water Views
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
- Patio
Coastal Osprey Retreat With Dock, Pool & Water Views
The 5-bedroom Coastal Osprey Retreat With Dock, Pool & Water Views Villa offers proximity to nearby tourist spots, such as Oscar Scherer State Park, situated around 10 minutes away by car.
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Beach access
Private House With Loft
- Free parking
- Air conditioning
- Tea and coffee facilities
- Jacuzzi
- Terrace
- Garden area
Located 2.5 km from Oscar Scherer State Park, the 2-bedroom Private House With Loft Villa Osprey entices guests to relax in a Jacuzzi. This villa hosts up to 4 guests and provides them with parking.
Private House With Loft
- Free parking
- Air conditioning
- Tea and coffee facilities
- Jacuzzi
- Terrace
- Garden area
Private House With Loft
Located 2.5 km from Oscar Scherer State Park, the 2-bedroom Private House With Loft Villa Osprey entices guests to relax in a Jacuzzi. This villa hosts up to 4 guests and provides them with parking.
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Popular choice
Tiny House Siesta
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Patio
Offering a picnic area and an outdoor shower for guests' leisure, Tiny House Siesta Villa Sarasota is situated about a 20-minute walk from Edson Keith Estate Park.
Tiny House Siesta
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Patio
Tiny House Siesta
Offering a picnic area and an outdoor shower for guests' leisure, Tiny House Siesta Villa Sarasota is situated about a 20-minute walk from Edson Keith Estate Park.
Lake Marlin Villa
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
Situated 2.7 km from Sunnybrook Alliance Church, the 2-bedroom Lake Marlin Villa Port Charlotte entices guests to explore various tourist attractions in the area.
Lake Marlin Villa
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
Lake Marlin Villa
Situated 2.7 km from Sunnybrook Alliance Church, the 2-bedroom Lake Marlin Villa Port Charlotte entices guests to explore various tourist attractions in the area.
Vera'S Vacation
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Saltwater pool
Situated within a 4-km distance of Smugglers Cove Adventure Golf, the 3-bedroom Vera'S Vacation Bradenton villa includes an outdoor swimming pool, as well as a Jacuzzi to relax in. Featuring garden views, the Bradenton holiday home invites guests to visit the South Florida Bishop Museum Of Science And Nature, located nearly a 15-minute drive away.
A sunbathing terrace, a picnic area, and a golf course are available at Vera'S Vacation villa, while sport lovers can try ping pong and billiard.
Vera'S Vacation
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Saltwater pool
Vera'S Vacation
Situated within a 4-km distance of Smugglers Cove Adventure Golf, the 3-bedroom Vera'S Vacation Bradenton villa includes an outdoor swimming pool, as well as a Jacuzzi to relax in. Featuring garden views, the Bradenton holiday home invites guests to visit the South Florida Bishop Museum Of Science And Nature, located nearly a 15-minute drive away.
A sunbathing terrace, a picnic area, and a golf course are available at Vera'S Vacation villa, while sport lovers can try ping pong and billiard.
Pirates Pointe Resort
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Heated swimming pool
Featuring an outdoor swimming pool for guests' relaxation, Pirates Pointe Resort Ruskin villa is located about 25 minutes on foot from Shell Point Cottage Gift Shop.
A terrace and a picnic area are available at Pirates Pointe Resort villa, while sport lovers can try canyoning and fisheries.
Pirates Pointe Resort
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Heated swimming pool
Pirates Pointe Resort
Featuring an outdoor swimming pool for guests' relaxation, Pirates Pointe Resort Ruskin villa is located about 25 minutes on foot from Shell Point Cottage Gift Shop.
A terrace and a picnic area are available at Pirates Pointe Resort villa, while sport lovers can try canyoning and fisheries.
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Beach access
Siesta Key Beachside Villas
- BBQ facilities
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Car park
US$ 10 per day
- Housekeeping
- Air conditioning
- Fitness centre
- Heated swimming pool
Offering bicycles for rent, the self-catering Siesta Key Beachside Villas Sarasota is located around a 5-minute walk from Beach Club. This accommodation is located 3.7 km from the Diverse South Lido County Waterfront Park and offers guests to enjoy a sunbathing terrace, a picnic area, and barbecue grills.
There is also an outdoor swimming pool, along with cycling.
Siesta Key Beachside Villas
- BBQ facilities
-
Car park
US$ 10 per day
- Housekeeping
- Air conditioning
- Fitness centre
- Heated swimming pool
Siesta Key Beachside Villas
Offering bicycles for rent, the self-catering Siesta Key Beachside Villas Sarasota is located around a 5-minute walk from Beach Club. This accommodation is located 3.7 km from the Diverse South Lido County Waterfront Park and offers guests to enjoy a sunbathing terrace, a picnic area, and barbecue grills.
There is also an outdoor swimming pool, along with cycling.
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Guest favorite
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Beach access
Siesta Key Beach Resort And Suites
- Cookware/ Kitchen utensils
-
Car park
US$ 10 per day
- Security
- Air conditioning
- Live entertainment
- Heated swimming pool
Siesta Key Beach Resort And Suites Sarasota villa is nestled nearly 20 minutes' walk from Siesta Key Beach and provides a Jacuzzi. Offering an outdoor swimming pool, the accommodation invites guests to visit the upscale Saint Armands Circle Outdoor Mall, located around 6 km away.
Siesta Key Beach Resort And Suites villa offers bicycles for rent, as well as access to a sunbathing terrace and a shared lounge to ensure an interesting stay. Guests can try different sport activities such as cycling.
Siesta Key Beach Resort And Suites
- Cookware/ Kitchen utensils
-
Car park
US$ 10 per day
- Security
- Air conditioning
- Live entertainment
- Heated swimming pool
Siesta Key Beach Resort And Suites
Siesta Key Beach Resort And Suites Sarasota villa is nestled nearly 20 minutes' walk from Siesta Key Beach and provides a Jacuzzi. Offering an outdoor swimming pool, the accommodation invites guests to visit the upscale Saint Armands Circle Outdoor Mall, located around 6 km away.
Siesta Key Beach Resort And Suites villa offers bicycles for rent, as well as access to a sunbathing terrace and a shared lounge to ensure an interesting stay. Guests can try different sport activities such as cycling.
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Beach access
The Sapphire Suite
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
The 1-bedroom The Sapphire Suite Sarasota villa hosts up to 2 guests and is nestled 4.7 km from natural sites such as Marie Selby Botanical Gardens. Located approximately 10 minutes' drive from Mote Marine Laboratory and Aquarium, the property provides Wi-Fi and parking.
The Sapphire Suite
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
The Sapphire Suite
The 1-bedroom The Sapphire Suite Sarasota villa hosts up to 2 guests and is nestled 4.7 km from natural sites such as Marie Selby Botanical Gardens. Located approximately 10 minutes' drive from Mote Marine Laboratory and Aquarium, the property provides Wi-Fi and parking.
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Private beach
Sunwashed Stone Villa With Heated Pool, Hot Tub & Mini Golf
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Heated swimming pool
Situated 4.7 km from the butterfly garden "Palma Sola Botanical Park", the 3-bedroom Sunwashed Stone Villa With Heated Pool, Hot Tub & Mini Golf Bradenton offers guests to enjoy a sunbathing terrace, a picnic area, and a golf course. Featuring a Jacuzzi, this holiday home is suitable for 8 people.
There is an outdoor swimming pool to relax, as well as mini golf.
Sunwashed Stone Villa With Heated Pool, Hot Tub & Mini Golf
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Heated swimming pool
Sunwashed Stone Villa With Heated Pool, Hot Tub & Mini Golf
Situated 4.7 km from the butterfly garden "Palma Sola Botanical Park", the 3-bedroom Sunwashed Stone Villa With Heated Pool, Hot Tub & Mini Golf Bradenton offers guests to enjoy a sunbathing terrace, a picnic area, and a golf course. Featuring a Jacuzzi, this holiday home is suitable for 8 people.
There is an outdoor swimming pool to relax, as well as mini golf.
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Best-rated
The Bungalows
- Cookware/ Kitchen utensils
- Flat-screen TV
- Tea and coffee facilities
- Fitness centre
- Patio
Offering a patio and barbecue for guests' leisure, The Bungalows Treasure Island is situated a 13-minute walk from John's Pass.
An outdoor swimming pool is featured at The Bungalows, as well as opportunity to participate in fitness classes.
The Bungalows
- Cookware/ Kitchen utensils
- Flat-screen TV
- Tea and coffee facilities
- Fitness centre
- Patio
The Bungalows
Offering a patio and barbecue for guests' leisure, The Bungalows Treasure Island is situated a 13-minute walk from John's Pass.
An outdoor swimming pool is featured at The Bungalows, as well as opportunity to participate in fitness classes.
Rock Creek Getaway
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Patio
Situated 3.9 km from The Cultural Center, the 3-bedroom Rock Creek Getaway Villa Port Charlotte entices guests to explore various tourist attractions in the area. This 2-bathroom villa hosts up to 6 guests and provides them with a private parking lot.
Rock Creek Getaway
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Patio
Rock Creek Getaway
Situated 3.9 km from The Cultural Center, the 3-bedroom Rock Creek Getaway Villa Port Charlotte entices guests to explore various tourist attractions in the area. This 2-bathroom villa hosts up to 6 guests and provides them with a private parking lot.
The Julia Place Carriage House
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
Located only a 5-minute stroll from Lukewood Park, the 1-bedroom The Julia Place Carriage House Sarasota villa gives easy access to various tourist attractions in the area. The Sarasota holiday home hosts up to 4 guests and provides them with private car parking.
The Julia Place Carriage House
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
The Julia Place Carriage House
Located only a 5-minute stroll from Lukewood Park, the 1-bedroom The Julia Place Carriage House Sarasota villa gives easy access to various tourist attractions in the area. The Sarasota holiday home hosts up to 4 guests and provides them with private car parking.
Spacious 3Br Sarasota Family Home 12 Min To Siesta Key Beach
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Flat-screen TV
- Patio
The 3-bedroom Spacious 3Br Sarasota Family Home 12 Min To Siesta Key Beach is situated merely 6 minutes' walk from Incarnation Catholic Church, featuring such comforts as Wi-Fi and a car park. The accommodation boasts a patio and barbecue, while Lido Key Sandy Beach is around 7 km away.
Spacious 3Br Sarasota Family Home 12 Min To Siesta Key Beach
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Flat-screen TV
- Patio
Spacious 3Br Sarasota Family Home 12 Min To Siesta Key Beach
The 3-bedroom Spacious 3Br Sarasota Family Home 12 Min To Siesta Key Beach is situated merely 6 minutes' walk from Incarnation Catholic Church, featuring such comforts as Wi-Fi and a car park. The accommodation boasts a patio and barbecue, while Lido Key Sandy Beach is around 7 km away.
On Island! Private Pool Home-Walk To Great Beach!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Outdoor swimming pool
Situated 1.2 km from the oceanfront Maxine Barritt Park, On Island! Private Pool Home-Walk To Great Beach! Venice is suitable for 8 guests and provides an outdoor swimming pool for additional relaxation. Located about a 25-minute walk from Waterway Park, this 3-bedroom villa provides Wi-Fi and a private parking lot.
On Island! Private Pool Home-Walk To Great Beach!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Outdoor swimming pool
On Island! Private Pool Home-Walk To Great Beach!
Situated 1.2 km from the oceanfront Maxine Barritt Park, On Island! Private Pool Home-Walk To Great Beach! Venice is suitable for 8 guests and provides an outdoor swimming pool for additional relaxation. Located about a 25-minute walk from Waterway Park, this 3-bedroom villa provides Wi-Fi and a private parking lot.
Are you in a hurry?
Here is a quick list of hotels in Osprey, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Tiny House Siesta |
8.1 / 10 (531 Reviews) |
From 5$ | |
| Lake Marlin Villa |
9.9 / 10 (88 Reviews) |
From 148$ | |
| Vera'S Vacation |
9.7 / 10 (47 Reviews) |
From 109$ | |
| Pirates Pointe Resort |
9.5 / 10 (77 Reviews) |
From 169$ | |
| Siesta Key Beachside Villas |
8.8 / 10 (296 Reviews) |
From 223$ |
Frequently Asked Questions
Which 5-star hotels in Siesta Key offer pool access?
The Sunwashed Stone Villa and Coastal Osprey Retreat both feature heated pools, perfect for relaxation after a day at the beach. Guests can enjoy the tropical landscape surrounding the pools.
Visit the Sunwashed Stone Villa on weekdays for a quieter experience at the pool before afternoon crowds arrive.
What are the best 5-star hotels in Siesta Key near the beach?
Siesta Key Beach Resort offers luxurious accommodations just steps away from Siesta Key Beach. You can enjoy the sun and surf without a long walk.
Stay at Siesta Key Beach Resort and head to the beach before 10 AM to secure a good spot on the sand during peak season.
Which 5-star hotels in Siesta Key offer views?
The Julia Place Carriage House features stunning water views. You can enjoy watching sunsets right from your room's balcony.
Request a room on the upper floor when booking at The Julia Place Carriage House to maximize your view of the coastline.
Are there 5-star hotels in Siesta Key that provide breakfast?
Many hotels, such as Siesta Key Beach Resort, include breakfast options for guests. Enjoy a meal before starting your day on the beach.
Try the local coffee shop, The Cottage, across from Siesta Key Beach for a delicious breakfast under $10 if you want an extra treat.
Which 5-star hotels in Siesta Key are romantic?
The Bungalows are perfect for couples seeking a romantic getaway. The intimate setting creates a cozy atmosphere.
Book a package that includes a couples' spa treatment to enhance your romantic experience during your stay.
What 5-star hotels in Siesta Key are pet-friendly?
Pirates Pointe Resort welcomes pets, allowing you to bring your furry friend along. This is perfect for animal lovers who want companionship on their trip.
Call ahead to confirm pet policies at Pirates Pointe Resort, as breed and size restrictions may apply.
Which 5-star hotels in Siesta Key offer extended stay options?
Coastal Osprey Retreat offers extended stay accommodations with all the comforts of home. Perfect for families or longer vacations.
Inquire about discounted rates for stays longer than a week at Coastal Osprey Retreat for better savings.
What unique experiences can I find in Siesta Key?
Siesta Key is famous for its powdery white sand beaches and vibrant nightlife. You can enjoy beach parties and live music events almost every weekend.
Visit during the Siesta Key Crystal Classic during November for sand sculpting competitions and local crafts to enjoy a true community experience.
How can I get around Siesta Key efficiently?
The best way to get around is by renting a bicycle or using local shuttles. It's an easy way to explore the area without parking hassles.
Rent a bike at least an hour before sunset for a lovely ride along the coast to enjoy the evening views.
What are the main attractions to visit in Siesta Key?
Siesta Key Beach and the nearby Siesta Key Village are must-visit spots. You can shop, dine, and enjoy beautiful sunsets here.
Visit Siesta Key Village in the late afternoon to catch the sunset at the beach right after your meal, creating the perfect end to your day.