Osprey, FL Vacation Homes from ￥17,019

Osprey Vacation Homes
Florida
United States of America
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A marina with docked boats, a wooden bridge, and a building with a red roof.

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Our top choices for Osprey vacation homes

An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees visible in the foreground.

A modern kitchen with a white countertop, a black kettle, a sink with a black faucet, and a hanging light fixture.

A modern living room with a flat-screen TV displaying 'NETFLIX', a dining area with a table and chairs, and a kitchen in the background.

A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with chairs and a table.

1. Charming Osprey Home

Charming Osprey Home

Bay Acres

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "

Diane S.

The price is ￥32,018

￥32,018

￥71,320 total

includes taxes & fees

Sep 8 - Sep 9

Charming Osprey Home

A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

A spacious living area with a large bed, a sofa, a small table, and a kitchen in the background.

A modern kitchen with white cabinets, a black countertop, and a red coffee maker.

A wooden deck overlooking a calm river, surrounded by lush greenery and trees.

2. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 star property

Siesta Key

8.4 out of 10, Very Good, (45 reviews)

8.4/10

Very Good

(45 reviews)

"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"

Christopher Robert

The price is ￥14,495

￥14,495

￥48,580 total

includes taxes & fees

Sep 1 - Sep 2

Siesta Heron Suites & Villas

A dining table set with plates, glasses, and a decorative glass holder.

A modern kitchen with wooden cabinets, stainless steel appliances, granite countertops, and a central island with seating.

A living room with two sofas, a coffee table, and a ceiling fan. There are two side tables with decorative items.

An outdoor patio with wicker furniture, a striped umbrella, and a view of a backyard with a fence and trees.

3. Beachside Bliss: Family House-Siesta Key-3BR/2BA

Beachside Bliss: Family House-Siesta Key-3BR/2BA

Sarasota

10.0 out of 10, Exceptional, (28 reviews)

10/10

Exceptional

(28 reviews)

"Great property! Very clean and spacious. Perfect for what we needed and close to Siesta Key and Gulf Gate restaurants and bars,"

Lori B.

The price is ￥16,857

￥16,857

￥56,045 total

includes taxes & fees

Sep 6 - Sep 7

Beachside Bliss: Family House-Siesta Key-3BR/2BA

A wooden pathway leading to a beach with clear turquoise water and a wooden railing on one side.

A swimming pool with a glass enclosure, surrounded by patio furniture and plants.

A covered outdoor area with a concrete path, surrounded by various tropical plants and a palm tree.

A wooden boardwalk leading to a beach with palm trees and a clear sky.

4. Tropical Villas of Venice Beach

Tropical Villas of Venice Beach

3.5 star property

Venice Island

9.6 out of 10, Exceptional, (268 reviews)

9.6/10

Exceptional

(268 reviews)

"It was amazing and way beyond what I thought. Easy walk to beach(0.4 mikes) and shops. Private location with small pool. Just what you need."

Christina

The price is ￥15,061

￥15,061

￥17,019 total

includes taxes & fees

Sep 1 - Sep 2

Tropical Villas of Venice Beach

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A spacious living area with a dining table, white chairs, a chandelier, and a large window overlooking a pool.

A modern living room with a beige sofa, a coffee table, and a chandelier. There is a kitchen area in the background with a dining table and chairs.

A modern kitchen with a large island, stainless steel appliances, and a dining area with a gray sofa and coffee table.

5. Siesta Key Island Rentals

Siesta Key Island Rentals

3.0 star property

Siesta Key

9.6 out of 10, Exceptional, (80 reviews)

9.6/10

Exceptional

(80 reviews)

"Great location, very clean and spacious."

Jason

The price is ￥18,410

￥18,410

￥54,407 total

includes taxes & fees

Sep 2 - Sep 3

Siesta Key Island Rentals

A wooden deck with a railing overlooking a lake, surrounded by lush greenery.

A modern kitchen with stainless steel appliances, a central island with bar stools, and a large window providing natural light.

6. Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Siesta Key

9.2 out of 10, Wonderful, (38 reviews)

9.2/10

Wonderful

(38 reviews)

"Very nice, clean and quiet place."

Monika Z.

The price is ￥36,493

￥36,493

￥72,598 total

includes taxes & fees

Sep 1 - Sep 2

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

A covered patio area with a blue sofa and a table, a wooden sculpture, and a dolphin wall art piece.

A bedroom with a bed, nightstand, lamp, and a ceiling fan.

A living room with a sofa, a TV, a small table, and a chair. There is a door leading to another room.

7. The Dolphin

The Dolphin

Nokomis

9.8 out of 10, Exceptional, (17 reviews)

9.8/10

Exceptional

(17 reviews)

"The cottage was comfortable and the pool was relaxing. "

daniel

The price is ￥28,016

￥28,016

￥53,863 total

includes taxes & fees

Sep 1 - Sep 2

The Dolphin

A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

A modern living room with a grey sectional sofa, yellow cushions, a small round table, and a wicker basket.

A bathroom with a marble countertop, a copper vessel sink, dark cabinets, and a large mirror.

A bedroom with a bed, bedside tables, a ceiling fan, and curtains.

8. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes

Siesta Key

9.8 out of 10, Exceptional, (37 reviews)

9.8/10

Exceptional

(37 reviews)

"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"

Sue H.

The price is ￥11,542

￥11,542

￥44,570 total

includes taxes & fees

Sep 7 - Sep 8

[lounge like locals] walk to siesta beach +bikes

A beach with two wooden lounge chairs and a white umbrella.

A living room with a dark blue sofa, a white door with a glass window, and various wall decorations including a 'home sweet home' sign and a framed picture.

A covered outdoor seating area with wicker furniture and a view of a swimming pool.

A dining area with a rectangular table, six blue upholstered chairs, a vase with flowers, and a mirror on the wall.

9. Dream Home at Sarasota Gulf Estates Heated pool

Dream Home at Sarasota Gulf Estates Heated pool

Sarasota

9.8 out of 10, Exceptional, (38 reviews)

9.8/10

Exceptional

(38 reviews)

"Very clean, nice communicative hosts, you can tell they love that place there are a lot of cute personal touches. I felt safe here and it was quiet."

jennifer w.

The price is ￥28,816

￥28,816

￥81,486 total

includes taxes & fees

Sep 6 - Sep 7

Dream Home at Sarasota Gulf Estates Heated pool

A covered outdoor area with a pool, seating, and a view of the water.

A modern kitchen with a dining area, a living room with a sofa and a large mirror, and a view of the outside.

A modern kitchen with stainless steel appliances, a dining area with a wooden table set for four, and a living area with a sofa and coffee table.

A waterfront patio with lounge chairs and a lamp post.

10. Oceanfront home w/sunset views of Sarasota Bay

Oceanfront home w/sunset views of Sarasota Bay

Vamo

9.8 out of 10, Exceptional, (132 reviews)

9.8/10

Exceptional

(132 reviews)

"Excellent place to stay"

Bob E.

The price is ￥63,876

￥63,876

￥122,128 total

includes taxes & fees

Sep 19 - Sep 20

Oceanfront home w/sunset views of Sarasota Bay

A beach with waves and a bird flying near the shore.

A compact, modern interior with a loft bedroom, a seating area with a laptop, and a kitchenette.

A compact kitchen with wooden cabinets, a built-in seating area, a television, and a small table with a tablet.

A compact, well-lit interior with a bunk bed, seating area, kitchenette, and a television.

11. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta

Sarasota

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."

Kadina A.

The price is ￥17,610

￥17,610

￥32,466 total

includes taxes & fees

Sep 6 - Sep 7

The Mermaid at Tiny House Siesta

A cozy outdoor seating area with a fire pit, wicker furniture, and a view into the house.

A modern living room with a large flat-screen TV mounted on the wall, a wooden coffee table, two sofas, and decorative plants.

A residential property at night with a swimming pool, a covered patio, and a car parked in the driveway.

A rectangular swimming pool with clear blue water, surrounded by a white fence and various potted plants.

12. 3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!

3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!

Gulf Gate Estates

10.0 out of 10, Exceptional, (24 reviews)

10/10

Exceptional

(24 reviews)

"Family had a great vacation at this property in Gulf Gate. Very nice pool and deck area and comfortable and clean home, great location for Siesta and Turtle beaches. Host was responsive and a pleasure to deal with, check in/out very simple. We were happy with our stay. "

Martin F.

The price is ￥33,459

￥33,459

￥102,541 total

includes taxes & fees

Sep 1 - Sep 2

3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!

A modern kitchen with white cabinets, a dining area with a dark wooden table set for four, and a chandelier.

A beach umbrella with a blue floral pattern.

A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a coffee maker.

A modern kitchen with a built-in oven, a refrigerator, and a microwave. There is a dining area with a table set for four, and a living room with a sofa and a coffee table.

13. Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

Sarasota Springs

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Host is really friendly n helpful!! Loved our stay and would definitely stay again "

Kathryn K.

Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

A clear swimming pool with a pink float, surrounded by a covered area with chairs and a wooden fence.

A house with a red door, a patio with chairs, and a garden with tropical plants.

A pathway leading to a building with a wooden fence and vegetation on the left.

A kitchen with a dining area, wooden cabinets, a black refrigerator, and a window with blinds.

14. Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

Ridge Wood Heights

9.4 out of 10, Exceptional, (125 reviews)

9.4/10

Exceptional

(125 reviews)

"very convenient, it was right in front of the event center that my daughter was dancing."

erica

The price is ￥24,814

￥24,814

￥45,826 total

includes taxes & fees

Sep 1 - Sep 2

Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a tiled backsplash.

A white door with a green wreath, a black wall-mounted light, and a framed sign with a welcoming message.

A neatly made bed with white linens and a wooden bench in front. There are two bedside tables with lamps, a painting above the bed, and a patterned rug on the floor.

A covered patio area with string lights, a door with a wreath, and a bench.

15. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Southgate

10.0 out of 10, Exceptional, (84 reviews)

10/10

Exceptional

(84 reviews)

"Her stay was outstanding everything was so professionally ready for us we felt at home comfortable the Privacy was impeccable"

James W.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

A coastal residential area with houses, a marina, and a clear view of the ocean.

A modern kitchen with white cabinets, a dining area with wicker chairs and a glass table, and a large window with a view.

A modern living room with a wooden ceiling, a beige sofa, two armchairs, a coffee table, and large windows with blinds.

16. Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

Nokomis

10.0 out of 10, Exceptional, (18 reviews)

10/10

Exceptional

(18 reviews)

"Great place close to beach and great food restaurants "

Adan M.

The price is ￥24,255

￥24,255

￥60,203 total

includes taxes & fees

Sep 1 - Sep 2

Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

A modern kitchen with a central island, a dining area with a table and chairs, and a living area with a sofa and a wall-mounted TV.

An outdoor seating area with a 'WELCOME' sign, wooden benches, and a blue chair.

A compact kitchen with a refrigerator, microwave, and sink, a small dining area with a white table and two chairs, and a sofa with a floral pattern.

17. Sea Turtle- Full Sized living at Tiny House Siesta

Sea Turtle- Full Sized living at Tiny House Siesta

Sarasota

9.4 out of 10, Exceptional, (18 reviews)

9.4/10

Exceptional

(18 reviews)

"The Tiny House is a perfect location to explore Siesta Key and the surrounding areas. It had just what we needed but was in close proximity (walking distance) to many bars and restaurants but was still exceptionally quiet."

Wayne

Sea Turtle- Full Sized living at Tiny House Siesta

A lifeguard tower with a red exterior, a flagpole with an American flag, and a beach with people and buildings in the background.

A modern dining area with a long table, chairs, and a ceiling light fixture.

A swimming pool with lounge chairs and an umbrella, surrounded by a white fence and a building with large windows.

18. Poolside Paradise Near Siesta Key Beach

Poolside Paradise Near Siesta Key Beach

Bee Ridge

8.8 out of 10, Excellent, (12 reviews)

8.8/10

Excellent

(12 reviews)

"Our family of 11 had a truly wonderful stay. The pool was most definitely a highlight."

Fannie Marie S.

The price is ￥32,221

￥32,221

￥71,550 total

includes taxes & fees

Sep 2 - Sep 3

Poolside Paradise Near Siesta Key Beach

A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

A modern kitchen with white cabinets, a central island, and a dining area with orange chairs and a red table.

A spacious living room with a high ceiling, a ceiling fan, a dining area with orange chairs, and a large gray sofa.

A modern kitchen with white cabinets, a coffee maker, and a sink. There is a window with blinds and a door leading to a balcony.

19. Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village

Siesta Key Village

8.4 out of 10, Very Good, (14 reviews)

8.4/10

Very Good

(14 reviews)

"Great place to stay and very close to restaurants "

Amber B.

The price is ￥14,728

￥14,728

￥60,655 total

includes taxes & fees

Sep 1 - Sep 2

Island Villa | Cozy Beach Retreat | Walk to Village

A modern living room with a grey sofa, ottoman, and a flat-screen TV mounted on the wall.

A modern kitchen with a white countertop, wooden stools, and a potted plant.

A dining area with a wooden table and chairs, a bench, and two windows with blinds.

20. Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

Nokomis

10.0 out of 10, Exceptional, (46 reviews)

10/10

Exceptional

(46 reviews)

"Great spot close to many attractions. Very well appointed with all that you need for a great vacation!"

Suzanne G.

The price is ￥29,490

￥29,490

￥68,294 total

includes taxes & fees

Sep 1 - Sep 2

Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Osprey Hotel Reviews

The Westin Sarasota

10/10 Excellent

"Great location excellent view front 19 floor from the pool"

Orlando 1-night trip

Posted less than an hour ago

The Westin Sarasota

Embassy Suites by Hilton Sarasota, FL

10/10 Excellent

"Me encantó"

Natalia 1-night trip

Posted less than an hour ago

Embassy Suites by Hilton Sarasota, FL

Siesta Key Beach Resort and Suites

10/10 Excellent

"Beautiful place, super friendly staff great location with all the bars and restaurants in walking distance!"

Mark 4-night trip

Posted 1 hour ago

Siesta Key Beach Resort and Suites

Lido Beach Resort

10/10 Excellent

"Wonderful staff, clean hotel, and perfect location with lots to do nearby."

Faris 5-night trip

Posted 2 hours ago

Lido Beach Resort

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent

"Great place to stay"

Maria 3-night trip

Posted 2 hours ago

Hyatt Place Sarasota/Bradenton Airport

Carlisle Inn

10/10 Excellent

"By far the best Inn I have ever stay in. Staff was incredible. I would love to visit again."

Damien 1-night trip

Posted 2 hours ago

Carlisle Inn

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"Property excellent condition and excellent location, I like this property, I”m recommending 100 %.. thanks for your team and services"

Jose A 3-night trip

Posted 4 hours ago

Spark by Hilton Sarasota Siesta Key Gateway

Inn at the Beach

10/10 Excellent

"The property and staff are all amazing."

Nicole 4-night trip

Posted 5 hours ago

Inn at the Beach

Tropical Beach Resorts

10/10 Excellent

"Great pool beautiful property. Rooms were sound proof. Never heard a peep out of a neighbor. Short walk to beach. Great room all round , catch trolley right outside property no need for convience."

Rose 2-night trip

Posted 5 hours ago

Tropical Beach Resorts

Find out more about Osprey

Osprey Vacation Homes information

Number of reviews	314
Accommodation	3972 Vacation Homes
Lowest Price	￥17,019
Highest Price	￥75,441

Explore a world of travel with Expedia

More ways to book

Book Vacation Homes in Osprey on Expedia.com

Search Vacation Homes in Osprey

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osprey vacation homes

1. Charming Osprey Home

2. Siesta Heron Suites & Villas

3. Beachside Bliss: Family House-Siesta Key-3BR/2BA

4. Tropical Villas of Venice Beach

5. Siesta Key Island Rentals

6. Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

7. The Dolphin

8. [lounge like locals] walk to siesta beach +bikes

9. Dream Home at Sarasota Gulf Estates Heated pool

10. Oceanfront home w/sunset views of Sarasota Bay

11. The Mermaid at Tiny House Siesta

12. 3bd 3b Siesta Key with New Heated Pool and a Game Room 2.5 Miles to the Beach!

13. Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

14. Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

15. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

16. Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

17. Sea Turtle- Full Sized living at Tiny House Siesta

18. Poolside Paradise Near Siesta Key Beach

19. Island Villa | Cozy Beach Retreat | Walk to Village

20. Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

The Westin Sarasota

Find out more about Osprey

Osprey Vacation Homes information

Explore a world of travel with Expedia