Vacation rentals in Osprey, FL

Best vacation rentals and Airbnb offers in Osprey, FL

Cozy studio in vibrant Sarasota, steps from Siesta waters, AC, WiFi

Apartment, Osprey

Cozy studio in vibrant Sarasota, steps from Siesta waters, AC, WiFi is a apartment in Osprey, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy studio in vibrant Sarasota, steps from Siesta waters, AC, WiFi

Cozy studio in vibrant Sarasota, steps from Siesta waters, AC, WiFi is a apartment in Osprey, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $807.

From$115/night

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5 Mi to Beach: Family Retreat in Sarasota!

Cottage, Osprey

5 Mi to Beach: Family Retreat in Sarasota! is a cottage in Osprey, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 5 Mi to Beach: Family Retreat in Sarasota!

5 Mi to Beach: Family Retreat in Sarasota! is a cottage in Osprey, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,321.

From$125/night

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Quiet and Comfortable Condo Near Turtle Beach on Siesta Key

Condo, Osprey

Quiet and Comfortable Condo Near Turtle Beach on Siesta Key is a condo in Osprey, with pool access, easy beach access, and a quieter setting. This stay gives travelers a comfortable base…

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About Quiet and Comfortable Condo Near Turtle Beach on Siesta Key

Quiet and Comfortable Condo Near Turtle Beach on Siesta Key is a condo in Osprey, with pool access, easy beach access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $942.

From$135/night

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Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025!

Holiday Home, Osprey

Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025! is a holiday home in Osprey, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025!

Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025! is a holiday home in Osprey, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $958.

From$137/night

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Vacation rentals with a pool in Osprey, FL

Add a pool to the search when you want an easy place to cool off between outings.

Windsor Lodge Unit #19, studio close to beaches

Apartment, Osprey

Windsor Lodge Unit #19, studio close to beaches is a apartment in Osprey, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Windsor Lodge Unit #19, studio close to beaches

Windsor Lodge Unit #19, studio close to beaches is a apartment in Osprey, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,528.

From$218/night

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Windsor Lodge Unit 10, Studio, close to the beaches, pool access

Apartment, Osprey

Windsor Lodge Unit 10, Studio, close to the beaches, pool access is a apartment in Osprey, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Windsor Lodge Unit 10, Studio, close to the beaches, pool access

Windsor Lodge Unit 10, Studio, close to the beaches, pool access is a apartment in Osprey, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,528.

From$218/night

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Windsor Lodge Unit 15, studio, close to the beaches, pool access

Apartment, Osprey

Windsor Lodge Unit 15, studio, close to the beaches, pool access is a apartment in Osprey, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Windsor Lodge Unit 15, studio, close to the beaches, pool access

Windsor Lodge Unit 15, studio, close to the beaches, pool access is a apartment in Osprey, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,528.

From$218/night

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Windsor Lodge Unit 3, studio, close to the beaches, pool access

Apartment, Osprey

Windsor Lodge Unit 3, studio, close to the beaches, pool access is a apartment in Osprey, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Windsor Lodge Unit 3, studio, close to the beaches, pool access

Windsor Lodge Unit 3, studio, close to the beaches, pool access is a apartment in Osprey, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,528.

From$218/night

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Vacation rentals with parking in Osprey, FL

Find vacation rentals that make arriving by car easier.

Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock

Condo, Osprey

Dolphin at Coastal Breeze · Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock is a condo in Osprey, with easy beach access, outdoor space, and parking. This stay gives…

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About Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock

Dolphin at Coastal Breeze · Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock is a condo in Osprey, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,218.

From$174/night

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Coastal Breeze Siesta - Manatee

Condo, Osprey

Coastal Breeze Siesta - Manatee is a condo in Osprey, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Coastal Breeze Siesta - Manatee

Coastal Breeze Siesta - Manatee is a condo in Osprey, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, beachfront, beach front, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,786.

From$178/night

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Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing

Condo, Osprey

Turtle at Coastal Breeze · Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing is a condo in Osprey, with easy beach access, parking, and kitchen access. This stay…

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About Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing

Turtle at Coastal Breeze · Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing is a condo in Osprey, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,274.

From$182/night

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Cozy beach bungalow

Holiday Home, Osprey

Cozy beach bungalow is a holiday home in Osprey, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy beach bungalow

Cozy beach bungalow is a holiday home in Osprey, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,420.

From$203/night

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Pet-friendly vacation rentals in Osprey, FL

Bring your pet along with stays that welcome four-legged travelers.

1 Mi to Nokomis Beach: Quiet Getaway w/ Fire Pit

Apartment, Osprey

1 Mi to Nokomis Beach: Quiet Getaway w/ Fire Pit is a apartment in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About 1 Mi to Nokomis Beach: Quiet Getaway w/ Fire Pit

1 Mi to Nokomis Beach: Quiet Getaway w/ Fire Pit is a apartment in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $822.

From$83/night

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Studio On Walking Distance To \"Kasey Kay\" Beach

Apartment, Osprey

Studio On Walking Distance To \"Kasey Kay\" Beach is a apartment in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Studio On Walking Distance To \"Kasey Kay\" Beach

Studio On Walking Distance To \"Kasey Kay\" Beach is a apartment in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $638.

From$91/night

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Renovated Tranquil 3-Bdrm- w/ yard, workspace, great kitchen in Osprey dogs ok

Holiday Home, Osprey

Renovated Tranquil 3-Bdrm- w/ yard, workspace, great kitchen in Osprey dogs ok is a holiday home in Osprey, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Renovated Tranquil 3-Bdrm- w/ yard, workspace, great kitchen in Osprey dogs ok

Renovated Tranquil 3-Bdrm- w/ yard, workspace, great kitchen in Osprey dogs ok is a holiday home in Osprey, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,395.

From$199/night

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Charming Osprey Home

Holiday Home, Osprey

Charming Osprey Home is a holiday home in Osprey, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Osprey Home

Charming Osprey Home is a holiday home in Osprey, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,477.

From$211/night

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Vacation rentals with a kitchen in Osprey, FL

Compare stays with kitchen access for longer trips and easier meals.

< 1 Mi to Nokomis Beach: Tranquil Couples Retreat

Apartment, Osprey

< 1 Mi to Nokomis Beach: Tranquil Couples Retreat is a apartment in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About < 1 Mi to Nokomis Beach: Tranquil Couples Retreat

< 1 Mi to Nokomis Beach: Tranquil Couples Retreat is a apartment in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $973.

From$102/night

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Coastal Studio Getaway|5 Min to Beach|Pool

Holiday Home, Osprey

Coastal Studio Getaway · 5 Min to Beach · Pool is a holiday home in Osprey, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for…

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About Coastal Studio Getaway|5 Min to Beach|Pool

Coastal Studio Getaway · 5 Min to Beach · Pool is a holiday home in Osprey, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $921.

From$132/night

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Charming 2-bedroom house in welcoming Sarasota with AC

Holiday Home, Osprey

Charming 2-bedroom house in welcoming Sarasota with AC is a holiday home in Osprey, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Charming 2-bedroom house in welcoming Sarasota with AC

Charming 2-bedroom house in welcoming Sarasota with AC is a holiday home in Osprey, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,409.

From$201/night

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Windsor Lodge Unit 5, studio, close to the beaches, pool access

Apartment, Osprey

Windsor Lodge Unit 5, studio, close to the beaches, pool access is a apartment in Osprey, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Windsor Lodge Unit 5, studio, close to the beaches, pool access

Windsor Lodge Unit 5, studio, close to the beaches, pool access is a apartment in Osprey, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,528.

From$218/night

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Family-friendly vacation rentals in Osprey, FL

Plan a trip with stays that give families more room to spread out.

Perfect Getaway-Lovely Cottage House- Near Beaches

B & B, Osprey

Perfect Getaway-Lovely Cottage House- Near Beaches is a b & b in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Perfect Getaway-Lovely Cottage House- Near Beaches

Perfect Getaway-Lovely Cottage House- Near Beaches is a b & b in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $815.

From$85/night

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Cottage within walking distance to Casey Key Beach

Cottage, Osprey

Cottage within walking distance to Casey Key Beach is a cottage in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Cottage within walking distance to Casey Key Beach

Cottage within walking distance to Casey Key Beach is a cottage in Osprey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $644.

From$92/night

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KeyLime Cottage - Beachy Getaway 3 Min. From Beach

Holiday Home, Osprey

KeyLime Cottage - Beachy Getaway 3 Min. From Beach is a holiday home in Osprey, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About KeyLime Cottage - Beachy Getaway 3 Min. From Beach

KeyLime Cottage - Beachy Getaway 3 Min. From Beach is a holiday home in Osprey, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $863.

From$123/night

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4 Mi to Siesta Key: Family Getaway w/ Balcony

Cottage, Osprey

4 Mi to Siesta Key: Family Getaway w/ Balcony is a cottage in Osprey, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 4 Mi to Siesta Key: Family Getaway w/ Balcony

4 Mi to Siesta Key: Family Getaway w/ Balcony is a cottage in Osprey, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,790.

From$187/night

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