Osprey, FL Vacation Homes from AED 447

Osprey Vacation Homes
Florida
United States of America
Expedia.ae

A marina with docked boats, a wooden bridge, and a building with a red roof.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Osprey vacation homes

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

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

A modern kitchen with stainless steel appliances, a central island with bar stools, and a window with blinds.

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 star property

Siesta Key

8.4 out of 10, Very good, (46 reviews)

8.4/10

Very good

(46 reviews)

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

Christopher Robert

The price is AED 347

AED 347

AED 1,131 total

includes taxes & fees

20 Oct - 21 Oct

Siesta Heron Suites & Villas

A modern kitchen with a stainless steel sink, a dining area with a table and chairs, and a living room with a sofa and a TV.

A modern living room with a sofa, coffee table, and dining area with chairs and a table.

A dining room with a long table set for six, large windows, and a view of a pool and outdoor area.

A modern living room with a sofa, dining table, and bar stools. A kitchen with white cabinets and a refrigerator is visible in the background.

2. Oceanfront home

Oceanfront home

Vamo

9.8 out of 10, Exceptional, (94 reviews)

9.8/10

Exceptional

(94 reviews)

"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."

Ashley H.

Oceanfront home

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

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.

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

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)

"Very clean and tucked away in a quiet little neighborhood with everything you need within 10 mins...this place made for the most comfortable and perfect vacation!"

christy v.

The price is AED 370

AED 370

AED 1,260 total

includes taxes & fees

29 Oct - 30 Oct

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

A modern kitchen with stainless steel appliances, a dining area with a round table and chairs, and a large window overlooking a backyard.

A modern kitchen with stainless steel appliances, a dining area with a round table and black chairs, and a living room with a sofa and a TV.

A hotel room with a bed, a ceiling fan, a TV displaying a beach scene, and a sliding glass door leading to an outdoor area.

A modern kitchen with white cabinets, stainless steel appliances, and a black granite countertop.

4. KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

Gulf Gate Estates

10.0 out of 10, Exceptional, (45 reviews)

10/10

Exceptional

(45 reviews)

"Our 2nd time here and we’ll be back again! Thanks Tim and family for such a great house!"

Angela K.

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

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.

A sign for Siesta Beach, a Sarasota County Park, located at 948 Beach Road.

5. 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)

"This is a beautiful place."

Pam J.

The price is AED 805

AED 805

AED 1,633 total

includes taxes & fees

26 Oct - 27 Oct

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

A covered patio with a round table and chairs, large windows, and a view of a backyard with a wooden fence and palm trees.

A dining area with a round table set for four, surrounded by chairs. There is a kitchen area with white cabinets and a microwave.

A single-story house with a garage, a small front yard, and a tree.

A living room with a white sofa, striped armchairs, a wooden coffee table, a ceiling fan, and a TV on the wall.

6. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key

Sarasota

9.8 out of 10, Exceptional, (86 reviews)

9.8/10

Exceptional

(86 reviews)

"Clean and convenient"

Scott H.

2 miles to #1 Beach Siesta Key

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

A kitchen with wooden cabinets, stainless steel appliances, a built-in oven, and a coffee maker.

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.

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.

7. 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

The price is AED 378

AED 378

AED 716 total

includes taxes & fees

20 Oct - 21 Oct

Sea Turtle- Full Sized living at Tiny House Siesta

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

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

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

A kitchen with white cabinets, a stainless steel sink, a microwave, an oven, and a trash can.

8. The Dolphin

The Dolphin

Nokomis

9.8 out of 10, Exceptional, (21 reviews)

9.8/10

Exceptional

(21 reviews)

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

daniel

The price is AED 643

AED 643

AED 1,225 total

includes taxes & fees

20 Oct - 21 Oct

The Dolphin

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.

9. 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 Mermaid at Tiny House Siesta

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 dining area with wicker chairs, a round glass table, and a hanging light fixture.

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

10. 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)

"The property was immaculate and inviting! The beds provided great comfort, and the air conditioning was just right. The house was well-equipped, with beach items being a fantastic bonus. The location is unbeatable, and the beach itself was stunning. Highly recommend—10/10!"

Kimberly K.

The price is AED 516

AED 516

AED 1,321 total

includes taxes & fees

20 Oct - 21 Oct

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

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 bedroom with a bed, a ceiling fan, a window with curtains, a floor lamp, and a painting on the wall.

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

11. 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, (128 reviews)

9.4/10

Exceptional

(128 reviews)

"Beautiful home, perfect location! Would come back again. Thank you!!! "

Joe V.

The price is AED 569

AED 569

AED 1,040 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

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, (27 reviews)

10/10

Exceptional

(27 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 AED 852

AED 852

AED 2,441 total

includes taxes & fees

3 Nov - 4 Nov

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

A beach with clear blue water and a sandy shore.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a coffee maker. There are two blue chairs and a small table with bottles.

A living room with a sofa set, a wooden table, a ceiling fan, and a TV mounted on the wall.

A bedroom with a bed, a desk, a chair, a ceiling fan, and a door leading to a bathroom.

13. "The Lobster" at The Shore Beach Houses Resort

"The Lobster" at The Shore Beach Houses Resort

Nokomis

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Thanks so much, great space and location! Would love to come back. "

Ashley

"The Lobster" at The Shore Beach Houses Resort

A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

A turquoise two-story house with a white garage door, surrounded by a wooden fence and palm trees.

A living room with a grey sofa, teal ottoman, and a potted plant.

A room with a round white table, a vase with yellow flowers, and a view of a garden through a sliding glass door.

14. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway

Siesta Key

9.8 out of 10, Exceptional, (34 reviews)

9.8/10

Exceptional

(34 reviews)

"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"

Tim T.

[escape to paradise] siesta key beach getaway

A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

A modern kitchen with white cabinets, a blue countertop, and a dining area with a round table and grey chairs.

A modern kitchen with a dining area, featuring a white countertop, blue cabinets, and a round table with chairs.

A pool area with lounge chairs and a sign that reads "Life is better in flip flops."

15. Dolphin Villa | Pool | Steps to Siesta Key Village

Dolphin Villa | Pool | Steps to Siesta Key Village

Siesta Key Village

9.4 out of 10, Exceptional, (17 reviews)

9.4/10

Exceptional

(17 reviews)

"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "

Amy

The price is AED 401

AED 401

AED 1,350 total

includes taxes & fees

22 Oct - 23 Oct

Dolphin Villa | Pool | Steps to Siesta Key Village

A narrow hallway leading to a bathroom with a vanity, shelves with storage bins, and a chandelier.

A house with a 'WELCOME' sign, a covered patio, a covered patio, and a gravel driveway.

A bedroom with a bed, a television, a desk, and a sliding glass door leading to a patio.

A bathroom with a bathtub, toilet, vanity with a sink, mirror, and a toilet paper holder.

16. Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.

Sarasota Springs

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great 1 bedroom/1 bath in a quiet neighborhood. Friendly host. Accommodations were very accurately described. There is a mini fridge which was a nice convenience to have."

Larry H.

The price is AED 184

AED 184

AED 447 total

includes taxes & fees

24 Oct - 25 Oct

Cozy 1-bedroom private room in Sarasota.

A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

A covered outdoor area with a pool, a table with chairs, and a ceiling fan.

An aerial view of a residential area with a large house featuring a spacious backyard, a swimming pool, and a view of the ocean.

A dining area with a blue tablecloth, wooden chairs, and a plant centerpiece.

17. Siesta beach....one and only

Siesta beach....one and only

Sarasota

9.4 out of 10, Exceptional, (222 reviews)

9.4/10

Exceptional

(222 reviews)

"Nice stay perfect location"

tom f.

The price is AED 459

AED 459

AED 1,731 total

includes taxes & fees

21 Oct - 22 Oct

Siesta beach....one and only

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 modern kitchen with a central island, bar stools, and built-in appliances.

18. 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.

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

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

A modern living room with a grey sectional sofa, a round ottoman, a small table with a lamp, and a wall-mounted TV.

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 AED 591

AED 591

AED 1,706 total

includes taxes & fees

17 Nov - 18 Nov

Island Villa | Cozy Beach Retreat | Walk to Village

A bedroom with a bed, a green armchair, a yellow dresser, and a TV displaying a tropical scene.

A modern living room with a blue sofa, yellow armchair, and a white coffee table.

20. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Siesta Key Village

9.0 out of 10, Wonderful, (15 reviews)

9.0/10

Wonderful

(15 reviews)

"We loved staying here for my bachelorette!"

Kelsey E.

The price is AED 507

AED 507

AED 1,606 total

includes taxes & fees

22 Oct - 23 Oct

Everglades Villa • Sleeps 8 • Walk to Siesta Beach

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.

View all properties

Find vacation rentals that suit your style

Aparthotels

search for apart-hotels

Cabins

search for cabins

Cottages

search for cottages

Villas

search for villas

Apartments

search for apartments

Private vacation homes

search for private vacation homes

Condos

search for condos

Houseboats

search for houseboats

Save an average of 15% on thousands of hotels when you're signed in

Top Osprey Hotel Reviews

Kompose Boutique Hotel

10/10 Excellent

"We were only there for a quick stay but it was perfect for what we needed and we were lucky to catch a fun Bingo night!"

Amy 1-night trip

Posted 5 hours ago

Kompose Boutique Hotel

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"Todo"

Jorge Antonio 2-night trip

Posted 7 hours ago

Spark by Hilton Sarasota Siesta Key Gateway

Casey Key Resorts - Mainland

8/10 Good

"Great stay we only spend the night, not much time to use the amenities. The only was the A/C was not cooling enough but overall was a pleasure to stay at Casey."

Yadira 1-night trip

Posted 8 hours ago

Casey Key Resorts - Mainland

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent

"The room was clean, nice and very spacious The pool area was very nice and it was open late. The breakfast which was included with your stay was one of the best breakfasts I’ve had at a hotel with many options. Myself and my family would stay again."

Serene 1-night trip

Posted 8 hours ago

Hyatt Place Sarasota/Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent

"Nicely located near the airport. Good quality, and a reasonable price,"

William G 1-night trip

Posted 8 hours ago

DoubleTree by Hilton Sarasota Bradenton Airport

Golden Host Resort - Sarasota

8/10 Good

"Room was very clean and beds were extremely comfortable. Only negative was the outside light was not on when we arrived at night"

Marilyn 2-night trip

Posted 9 hours ago

Golden Host Resort - Sarasota

Tropical Beach Resorts

10/10 Excellent

"Wonderful stay overall!! Staff was very pleasant and helpful. Room was stocked and cleaned daily. The beach was a small walk away. The sand was white and powder soft. Property was clean and everything was easy access. Would definitely stay again"

Brandi 3-night trip

Posted 11 hours ago

Tropical Beach Resorts

Cottages at Siesta Key Inn

10/10 Excellent

"LOCATION. LOCATION. LOCATION. A short walk to Beach Access 13 and restaurants. Great location for watching the sunset. Our room was big, the bed was comfortable, the pool was amazing. The property was quiet. Private parking is appreciated. The staff are so friendly and helpful."

Amy 4-night trip

Posted 20 hours ago

Cottages at Siesta Key Inn

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. Siesta Heron Suites & Villas

2. Oceanfront home

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

4. KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

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

6. 2 miles to #1 Beach Siesta Key

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

8. The Dolphin

9. The Mermaid at Tiny House Siesta

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

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

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

13. "The Lobster" at The Shore Beach Houses Resort

14. [escape to paradise] siesta key beach getaway

15. Dolphin Villa | Pool | Steps to Siesta Key Village

16. Cozy 1-bedroom private room in Sarasota.

17. Siesta beach....one and only

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

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

20. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

Kompose Boutique Hotel