1+ Vacation Rentals Near Osprey |
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Cruises By Owner - Vacation Rentals in Osprey

Live on the water in a Sarasota Houseboat in a beautiful setting. From US $163
         

New
Boat Rental
Live on the water in a Sarasota Houseboat in a beautiful setting.
  • Air Conditioner
  • Child Friendly

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Luxury Places to Stay in Osprey

Over 112+ Luxury Places to Stay in or Near Osprey
Paradise with a pool, pier and private beach area From US $1,034
         

9.0 (20 Reviews)
Villa
Paradise with a pool, pier and private beach area
  • Air Conditioner
  • Parking
  • Pet Friendly

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Paradise with a pool, pier and private beach area From US $706
         

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

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Idyllic Casey Key Beach House From US $678
         

9.6 (36 Reviews)
House
Idyllic Casey Key Beach House
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bright & Comfortable Florida Cottage, Within 15 Min to Siesta and Nokomis Beach From US $506
         

10.0 (1 Review)
House
Bright & Comfortable Florida Cottage, Within 15 Min to Siesta and Nokomis Beach
  • Air Conditioner
  • Parking
  • TV

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Pet-Friendly Modern Retreat Near Siesta Key From US $504
         

10.0 (5 Reviews)
House
Pet-Friendly Modern Retreat Near Siesta Key
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront home with pool, dock accessible to Gulf, dog friendly with AC & WD From US $491
         

New
House
Waterfront home with pool, dock accessible to Gulf, dog friendly with AC & WD
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pool, Hot tub, Close to Beaches, Shopping, More! From US $425
         

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New
House
Pool, Hot tub, Close to Beaches, Shopping, More!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Mid-century Waterfront Home with pool From US $419
         

10.0 (38 Reviews)
House
Mid-century Waterfront Home with pool
  • Air Conditioner
  • Parking
  • Pool

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Top-Rated Vacation Rentals with a Pool in Osprey

Over 60+ Top-Rated Vacation Rentals with a Pool in or Near Osprey
Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches. From US $250
         

10.0 (6 Reviews)
Condo
Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
  • Air Conditioner
  • Parking
  • Pool

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Windsor Lodge Unit 10, Studio, close to the beaches, pool access From US $206
         

10.0 (3 Reviews)
Apartment
Windsor Lodge Unit 10, Studio, close to the beaches, pool access
  • Air Conditioner
  • Pool
  • TV

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2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view! From US $193
         

10.0 (3 Reviews)
Condo
2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!
  • Air Conditioner
  • Parking
  • Pool

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Cozy 1-bedroom condo in amazing Osprey, near the beach, WiFi, AC, Pool, Tennis From US $137
         

10.0 (1 Review)
Condo
Cozy 1-bedroom condo in amazing Osprey, near the beach, WiFi, AC, Pool, Tennis
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet Friendly Paradise Close To Sarasota-Venice From US $250
         

9.8 (59 Reviews)
House
Pet Friendly Paradise Close To Sarasota-Venice
  • Air Conditioner
  • Parking
  • Pet Friendly

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Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock From US $312
         

9.8 (11 Reviews)
House
Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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A Tropical 2 Bedroom/2 Bath House w/Pool and Dock From US $225
         

9.8 (6 Reviews)
House
A Tropical 2 Bedroom/2 Bath House w/Pool and Dock
  • Air Conditioner
  • Parking
  • Pool

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Huge Pool, Close to Beaches, Restaurants, Shopping & More! From US $287
         

9.6 (28 Reviews)
House
Huge Pool, Close to Beaches, Restaurants, Shopping & More!
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Osprey

Over 38+ Pet-Friendly Vacation Rentals in or Near Osprey
Modern luxe getaway for families near Siesta Key From US $318
         

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9.0 (3 Reviews)
House
Modern luxe getaway for families near Siesta Key
  • Air Conditioner
  • Parking
  • Pet Friendly

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4-bedroom heated pool house 5 minutes to the beach From US $247
         

10.0 (1 Review)
House
4-bedroom heated pool house 5 minutes to the beach
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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🌴 2BR Oasis w/Lanai, Fire Pit + 5 Min to Nokomis Beach From US $227
         

8.0 (2 Reviews)
House
🌴 2BR Oasis w/Lanai, Fire Pit + 5 Min to Nokomis Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy Cottage in south Sarasota Florida, Close to Beaches! From US $296
         

9.8 (7 Reviews)
Cottage
Cozy Cottage in south Sarasota Florida, Close to Beaches!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi From US $360
         

8.8 (28 Reviews)
House
Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
  • Air Conditioner
  • Parking
  • Pet Friendly

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Renovated duplex near beach with central AC & private W/D-Dogs ok From US $242
         

8.0 (2 Reviews)
House
Renovated duplex near beach with central AC & private W/D-Dogs ok
  • Air Conditioner
  • Parking
  • Pet Friendly

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4-bedroom heated Pool house in lovely Osprey, 5 minutes to the beach From US $345
         

6.0 (2 Reviews)
House
4-bedroom heated Pool house in lovely Osprey, 5 minutes to the beach
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens

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Charming 3-bedroom house with private pool, close to beaches and dining From US $296
         

New
House
Charming 3-bedroom house with private pool, close to beaches and dining
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Osprey

Over 4+ Large Vacation Homes & Villas in or Near Osprey
Royal Luxury Edenville House by Casey Key From US $359
         

New
House
Royal Luxury Edenville House by Casey Key
  • Air Conditioner
  • Pool
  • TV

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The Shoreland Hideaway 4BR & 2BA jacuzzi, minutes from Siesta Key From US $587
         

9.0 (15 Reviews)
House
The Shoreland Hideaway 4BR & 2BA jacuzzi, minutes from Siesta Key
  • Air Conditioner
  • Parking
  • Pet Friendly

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Full duplex near beach with renovated interior, screened porches-Dogs ok From US $312
         

New
House
Full duplex near beach with renovated interior, screened porches-Dogs ok
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful 3 bed/ 2bath, plus office Executive Home with private pool & lanai. From US $190
         

New
Villa
Beautiful 3 bed/ 2bath, plus office Executive Home with private pool & lanai.
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens

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Wheelchair Accessible Vacation Homes in Osprey

Over 7+ Wheelchair Accessible Vacation Homes in or Near Osprey
Casey Key Resorts - Mainland From US $205
         

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

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Casey Key Resorts - Mainland From US $124
         

8.8 (1119 Reviews)
Hotel
Casey Key Resorts - Mainland
  • Air Conditioner
  • Parking
  • Pool

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Windsor Lodge Unit 15, studio, close to the beaches, pool access From US $220
         

9.0 (2 Reviews)
Apartment
Windsor Lodge Unit 15, studio, close to the beaches, pool access
  • Air Conditioner
  • Parking
  • Pool

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Windsor Lodge Unit 3, studio, close to the beaches, pool access From US $223
         

8.8 (3 Reviews)
Apartment
Windsor Lodge Unit 3, studio, close to the beaches, pool access
  • Air Conditioner
  • Parking
  • Pool

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Hidden Gem in Hidden Bay From US $341
         

New
Condo
Hidden Gem in Hidden Bay
  • Air Conditioner
  • Parking
  • Pool

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Two Bedroom, Two Bath First Floor Condo From US $153
         

New
Condo
Two Bedroom, Two Bath First Floor Condo
  • Air Conditioner
  • Pool
  • Wheelchair Accessible

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Windsor Lodge Unit 3, studio, close to beaches, pool From US $140
         

New
Apartment
Windsor Lodge Unit 3, studio, close to beaches, pool
  • Air Conditioner
  • Parking
  • Pool

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Osprey Varoom and Airbnb Places to Stay Under $200

Over 36+ Osprey Varoom and Airbnb Places to Stay Under $200
Sand Dollar Retreat From US $180
         

New
House
Sand Dollar Retreat
  • Air Conditioner
  • Parking
  • View

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Villa in Osprey that sleeps the whole family From US $184
         

9.8 (35 Reviews)
Apartment
Villa in Osprey that sleeps the whole family
  • Air Conditioner
  • Parking
  • TV

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Newly Renovated Tranquil 3-Bdrm Home in Osprey- Close to Beaches Dogs Okay From US $182
         

New
House
Newly Renovated Tranquil 3-Bdrm Home in Osprey- Close to Beaches Dogs Okay
  • Air Conditioner
  • Parking
  • Pet Friendly

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Renovated Waterfront Home From US $142
         

9.6 (5 Reviews)
House
Renovated Waterfront Home
  • Air Conditioner
  • Parking
  • Pet Friendly

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Windsor Lodge Unit 19, studio, 1BR/1BA, close to the Beaches, pool access From US $190
         

New
Apartment
Windsor Lodge Unit 19, studio, 1BR/1BA, close to the Beaches, pool access
  • Air Conditioner
  • Pool
  • TV

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Enjoy your own 2bd/2ba Condo, Pool, Pickleball, Tennis, amazing sunsets! From US $163
         

New
Condo
Enjoy your own 2bd/2ba Condo, Pool, Pickleball, Tennis, amazing sunsets!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Fall is the best time! To vacation here,nAvail ALL Autumn till NYE 2025! From US $154
         

New
House
Fall is the best time! To vacation here,nAvail ALL Autumn till NYE 2025!
  • Air Conditioner
  • Parking
  • TV

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Windsor Lodge at the Oaks 1 From US $108
         

New
Condo
Windsor Lodge at the Oaks 1
  • Air Conditioner
  • Pool
  • Security/Safety

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Instantly Bookable Vacation Homes in Osprey

Over 23+ Instantly Bookable Vacation Homes in or Near Osprey
2BR Florida Home Near the Shore! From US $234
         

6.8 (3 Reviews)
House
2BR Florida Home Near the Shore!
  • Air Conditioner
  • Parking
  • Pet Friendly

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2-bedroom Spacious townhome in Osprey From US $226
         

10.0 (9 Reviews)
House
2-bedroom Spacious townhome in Osprey
  • Air Conditioner
  • Parking
  • TV

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Private guest house with king bed & loft. Deck with hot tub and putting green From US $261
         

10.0 (1 Review)
House
Private guest house with king bed & loft. Deck with hot tub and putting green
  • Air Conditioner
  • Parking
  • TV

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Cozy beach bungalow From US $215
         

10.0 (1 Review)
House
Cozy beach bungalow
  • Air Conditioner
  • Parking
  • TV

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COZY BEACH RETREAT JUST MINUTES AWAY FROM BEACH From US $237
         

9.0 (2 Reviews)
Condo
COZY BEACH RETREAT JUST MINUTES AWAY FROM BEACH
  • Air Conditioner
  • Parking
  • Pool

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3 BR Charming cozy coastal house🐬minutes away from Siesta Key & Venice beach From US $221
         

7.6 (5 Reviews)
House
3 BR Charming cozy coastal house🐬minutes away from Siesta Key & Venice beach
  • Air Conditioner
  • Parking
  • TV

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Luxurious 3/2 Waterfront Retreat in Osprey, FL! From US $318
         

New
Condo
Luxurious 3/2 Waterfront Retreat in Osprey, FL!
  • Air Conditioner
  • Parking
  • Pool

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Soothing 3-bedroom house with pool and boat dock in Osprey From US $301
         

New
House
Soothing 3-bedroom house with pool and boat dock in Osprey
  • Air Conditioner
  • Parking
  • Pool

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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 Cruisesbyowner 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.

Cruisesbyowner 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: Cruisesbyowner makes it easy to compare the best listings on Cruisesbyowner homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruisesbyowner 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

Top Attractions Around Osprey, FL

Cruisesbyowner offers a large selection of top attractions around Osprey. Research things to do on your vacation before you visit Osprey.


Oscar Scherer State Park Historic Spanish Point The Oaks Club Nancy's Consignments Lido Beach Venice Beach Siesta Key Beach St. Armands Circle Englewood Beach Turtle Beach IMG Academy Nokomis Beach Sarasota Jungle Gardens Mote Marine Laboratory & Aquarium Sarasota Memorial Hospital John and Mable Ringling Museum of Art Manasota Beach Crescent Beach Caspersen Beach Siesta Key Marina

Other Places to Stay Near Osprey, FL


Historic Spanish Point 831 Properties Nancy's Consignments 811 Properties The Oaks Club 763 Properties Bay Acres 647 Properties Sorrento Shores 555 Properties Oscar Scherer State Park 524 Properties Rivendell 380 Properties Osprey Village 44 Properties