Sell Off Cruises - Vacation Rentals in Osprey

Luxury Places to Stay in Osprey

Over 118+ Luxury Places to Stay in or Near Osprey
Rare private beachfront estate on the Gulf. From US $3,725
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Paradise with a pool, pier and private beach area From US $706
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Paradise with a pool, pier and private beach area From US $690
         

9.0 (22 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Idyllic Casey Key Beach House From US $678
         

9.6 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Osprey Home From US $439
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pool, Hot tub, Close to Beaches, Shopping, More! From US $425
         

Top-Rated Vacation Rentals with a Pool in Osprey

Over 63+ Top-Rated Vacation Rentals with a Pool in or Near Osprey
Mid-century Waterfront Home with pool From US $301
         

10.0 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Luxury Condo on the water with Intercostal view From US $151
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Pet Friendly Paradise Close To Sarasota-Venice From US $260
         

9.8 (59 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Osprey

Over 42+ Pet-Friendly Vacation Rentals in or Near Osprey
Pet-Friendly Modern Retreat Near Siesta Key From US $355
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern luxe getaway for families near Siesta Key From US $318
         

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9.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
🌴 2BR Oasis w/Lanai, Fire Pit + 5 Min to Nokomis Beach From US $227
         

8.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
4-bedroom heated pool house 5 minutes to the beach From US $267
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Cozy Cottage in south Sarasota Florida, Close to Beaches! From US $263
         

9.8 (7 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Renovated duplex near beach with central AC & private W/D-Dogs ok From US $247
         

4-bedroom heated Pool house in lovely Osprey, 5 minutes to the beach From US $297
         

6.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens
See More Pet-Friendly Vacation Rentals in Osprey on PetFriendly.io

Large Vacation Homes & Villas in Osprey

Over 4+ Large Vacation Homes & Villas in or Near Osprey
The Shoreland Hideaway 4BR & 2BA jacuzzi, minutes from Siesta Key From US $587
         

Wheelchair Accessible Vacation Homes in Osprey

Over 9+ Wheelchair Accessible Vacation Homes in or Near Osprey
Casey Key Resorts - Mainland From US $205
         

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8.2 (642 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Casey Key Resorts - Mainland From US $193
         

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8.8 (1139 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Windsor Lodge Unit 3, studio, close to the beaches, pool access From US $220
         

Waterview condo in ideal location From US $218
         

New
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Hidden Gem in Hidden Bay From US $341
         

New
Condo
  • Air Conditioner
  • Parking
  • Pool
Two Bedroom, Two Bath First Floor Condo From US $153
         

New
Condo
  • Air Conditioner
  • Pool
  • Wheelchair Accessible

Osprey Varoom and Airbnb Places to Stay Under $200

Over 36+ Osprey Varoom and Airbnb Places to Stay Under $200
2-bedroom Spacious townhome in Osprey From US $194
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Sand Dollar Retreat From US $180
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View
COZY BEACH RETREAT JUST MINUTES AWAY FROM BEACH From US $191
         

Instantly Bookable Vacation Homes in Osprey

Over 26+ Instantly Bookable Vacation Homes in or Near Osprey
2BR Florida Home Near the Shore! From US $234
         

6.8 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy beach bungalow From US $208
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV

About Osprey Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Selloffcruises Osprey, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Osprey. Places to stay near Osprey with prices averaging $163 a night.

Selloffcruises makes it easy and safe to find and compare vacation rentals in Osprey with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Osprey

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Use these Quick Filters to Find a Vacation Rental in Osprey

Pro Tip: Selloffcruises makes it easy to compare the best listings on Selloffcruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Selloffcruises homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osprey.

Weather in Osprey

View the weather forecast for Osprey before booking your Osprey Vacation Rentals to confirm your best time to go.

December - February
High 79°F       Low 51°F
March - May
High 91°F       Low 53°F
June - August
High 92°F       Low 72°F
September - November
High 90°F       Low 57°F