Best Resorts in Osprey

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Aug 22 - Aug 24
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Sep 12 - Sep 14
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Oct 10 - Oct 12

Resorts in Osprey

Lido Beach Resort
Relax by the oceanfront pool surrounded by lounge chairs and shaded seating areas.

Lido Beach Resort

4.0 star property
8.8 out of 10, Excellent, (1004)
"It was our third time staying at Lido Resort and loved it! "
$319 nightly
The price is $360
Sep 1 - Sep 2
Total includes taxes and fees
Lido Beach Resort
Zota Beach Resort
Enjoy a meal with a view of the ocean from this spacious dining area, featuring a large window and modern chairs.

Zota Beach Resort

4.0 star property
9.0 out of 10, Wonderful, (1004)
"Great stay!"
$289 nightly
The price is $327
Sep 1 - Sep 2
Total includes taxes and fees
Zota Beach Resort
Siesta Key Beach Resort and Suites
Relax by the pool surrounded by palm trees and lounge chairs.

Siesta Key Beach Resort and Suites

2.5 star property
8.8 out of 10, Excellent, (1006)
"Very nice room, great pool, great service, great location, close to beach, fun area"
$214 nightly
The price is $241
Sep 1 - Sep 2
Total includes taxes and fees
Siesta Key Beach Resort and Suites
The Resort at Longboat Key Club
Relax by the serene pool surrounded by lush greenery and palm trees, with unobstructed ocean views.

The Resort at Longboat Key Club

4.0 star property
9.0 out of 10, Wonderful, (666)
"Excellent customer service. Gorgeous property and beach. Will stay here again. "
$441 nightly
The price is $498
Sep 1 - Sep 2
Total includes taxes and fees
The Resort at Longboat Key Club
Newly updated in family/pet friendly resort with all the amenities - near beach!
Relax in this stylish living area with a sofa, armchair, and wicker chairs, surrounded by large windows and a patterned rug.

Newly updated in family/pet friendly resort with all the amenities - near beach!

10.0 out of 10, Exceptional, (4)
"Each year our son competes in a skimboarding competion at Nokomis Beach. This property was only a short distance away and was convenient to travel back in forth to the beach over the long weekend. The residence was very clean, comfortable and either had (or in the resort) every possible amenity you could think of within arms reach. The VRBO description is very accurate and our family had zero issues during our stay. We recommend 100% and will consider staying again next year. "
$202 nightly
The price is $225
Aug 12 - Aug 13
Total includes taxes and fees
Newly updated in family/pet friendly resort with all the amenities - near beach!
Palm Bay Club Siesta Key Newley renovated !
Outdoor pool, a heated pool

Palm Bay Club Siesta Key Newley renovated !

9.4 out of 10, Exceptional, (27)
"We had a really nice stay. Great location!"
Palm Bay Club Siesta Key Newley renovated !
Wellen Park Golf & Country Club resort style single family house full furnished.
Relax in this stylish living room with two sofas and a glass coffee table.

Wellen Park Golf & Country Club resort style single family house full furnished.

Wellen Park Golf & Country Club resort style single family house full furnished.
Beautiful Venice Resort Home close to Beaches & Warm Mineral Springs, Cozy
Kitchen features a stainless steel range, oven, microwave, sink, coffee maker, and small window.

Beautiful Venice Resort Home close to Beaches & Warm Mineral Springs, Cozy

10.0 out of 10, Exceptional, (5)
"Niche place with it's own unique flavor. "
$350 nightly
The price is $390
Sep 1 - Sep 2
Total includes taxes and fees
Beautiful Venice Resort Home close to Beaches & Warm Mineral Springs, Cozy
Family fun amenities for all ages!Two bedroom ,sleeps 6, pet friendly ,relaxing.
Relax by the pool surrounded by a tiled deck and enjoy a refreshing swim in the clear blue waters.

Family fun amenities for all ages!Two bedroom ,sleeps 6, pet friendly ,relaxing.

Family fun amenities for all ages!Two bedroom ,sleeps 6, pet friendly ,relaxing.
Sunny Apartments a block from Warm Mineral Springs. Unit 3
Relax in style with a round table and comfortable seating, surrounded by a tranquil view.

Sunny Apartments a block from Warm Mineral Springs. Unit 3

8.2 out of 10, Very Good, (11)
"Close proximity to various beaches and services. The apartment was small but very comfortable with a modern well equipped kitchen. The apartment has been upgraded except the bathroom. We would stay there again"
Sunny Apartments a block from Warm Mineral Springs. Unit 3
Amenities galore
Cozy room with a vintage aesthetic, featuring a comfortable sofa, dining table, and unique detour sign.

Amenities galore

10.0 out of 10, Exceptional, (1)
"Kim was the greatest host! Cozy unit with everything I needed. Made me feel right at home. Great pool and all the amenities were awesome! Will definitely use again!"
Amenities galore
Sarasota NEWER CONDO IN LAKEWOOD NATIONAL GOLF & CLUB & SHORT DRIVE TO BEACHES
Relax by the pool surrounded by palm trees and lounge chairs.

Sarasota NEWER CONDO IN LAKEWOOD NATIONAL GOLF & CLUB & SHORT DRIVE TO BEACHES

10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay at Lakewood National. The condo had everything we needed and the amenities are terrific. We look forward to visiting again!"
Sarasota NEWER CONDO IN LAKEWOOD NATIONAL GOLF & CLUB & SHORT DRIVE TO BEACHES
Get away to the Country on a lake enjoying the wild life and horses.
Surrounded by lush greenery and mature pine trees, this serene setting features a peaceful pond with a tranquil atmosphere.

Get away to the Country on a lake enjoying the wild life and horses.

Get away to the Country on a lake enjoying the wild life and horses.
Charming 2-bedroom resort home minutes from the beaches with heated pools.
Enjoy a refreshing swim in our pool surrounded by a shaded deck and lifeguard supervision.

Charming 2-bedroom resort home minutes from the beaches with heated pools.

Charming 2-bedroom resort home minutes from the beaches with heated pools.
Veranda Beach front property and pool, school vacation week
Relax on the beach with comfortable sun loungers and umbrellas, steps from the ocean.

Veranda Beach front property and pool, school vacation week

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay. It was nice to have the beach service at no cost to us. There was an innocent mistake in our booking dates but the owner compensated us with a night's stay at another location at his expense. Highly recommend the area, condo & facility. We will definitely be going back!"
Veranda Beach front property and pool, school vacation week
Veranda Beach Club, ( Week 2 ) Jan. 11 to 18, 2020
Relax on the beach with comfortable sun loungers and umbrellas along the shoreline.

Veranda Beach Club, ( Week 2 ) Jan. 11 to 18, 2020

10.0 out of 10, Exceptional, (1)
"Great property and beautiful beach"
Veranda Beach Club, ( Week 2 ) Jan. 11 to 18, 2020
Beautiful Longboat Key, Florida - Little Gull Resort
Guests can enjoy swimming and wading in the ocean.

Beautiful Longboat Key, Florida - Little Gull Resort

Beautiful Longboat Key, Florida - Little Gull Resort
Waterfront Gulf view 3 bed/3 bath suite at Hyatt Residences on Siesta Key Beach.
Relax on the beachfront balcony with a comfortable seating area and stunning ocean views.

Waterfront Gulf view 3 bed/3 bath suite at Hyatt Residences on Siesta Key Beach.

Waterfront Gulf view 3 bed/3 bath suite at Hyatt Residences on Siesta Key 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.
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Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Nice property near Siesta Key with a nice pool. Enjoyed our stay"
Kim 2-night trip
Posted 14 hours ago
Spark by Hilton Sarasota Siesta Key Gateway