Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (217)
"Good location clean easy check in"
Tropical Villas of Venice Beach
Private Oasis in Sarasota Florida
Indoor pool

Private Oasis in Sarasota Florida

10.0 out of 10, Exceptional, (14)
"The property was just as described. A perfect spot. Close to everything but secluded. The owner was very receptive when a minor issue was addressed. Just the atmosphere we needed for rest and relaxation! "
Private Oasis in Sarasota Florida
Siesta Key Island Rentals
Room amenity

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals
2-Bedroom Pool Home Convenient To Beaches
Fridge, microwave, oven, stovetop

2-Bedroom Pool Home Convenient To Beaches

9.8 out of 10, Exceptional, (117)
"Super easy to rent - host very responsive. Basic accommodation with bonus swimming pool. Nice privacy factor. Convenient for our weekend trip to view area properties. "
2-Bedroom Pool Home Convenient To Beaches
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach
Beach

Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

9.2 out of 10, Wonderful, (5)
"Jennifer thanx for a great stay, it was so peaceful, and quiet. We loved the heated pool, the attention to detail. Such as lots of charging ports Jennifer thought of it all such as blowdryer, bug spray even toothbrushes. The beds we're super comfy. In the shed we used the cooler and beach made life easier."
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Fridge, microwave, oven, stovetop

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.8 out of 10, Exceptional, (77)
"We stayed for 5 nights and wished we could have stayed longer! The home was perfect for our needs with spacious rooms, clean and well taken care of, and all the amenities we could use. The pool and canal view were added bonuses. The location was especially great for us. We walked daily to the Village to enjoy the variety of restaurants and also the gorgeous public beach. The host was so responsive to questions and also helped us with a forgotten item. Above and beyond! Recommend so...
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Gorgeous Pool house 5 min from the beach, shopping and restaurants I
Sun-loungers, beach towels

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

9.2 out of 10, Wonderful, (35)
"This was a great home to stay in! My friend and I were in town for a birthday. The neighborhood is very safe and close to so many local spots. The owners were very responsive and helpful. "
The price is AU$578
includes taxes & fees
27 Nov - 28 Nov
Gorgeous Pool house 5 min from the beach, shopping and restaurants I
Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach
Beach nearby, sun-loungers, beach towels

Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach

10.0 out of 10, Exceptional, (129)
"Enjoyed our stay very much. Only downside the pool was a Littel cold."
Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach
Private Home | Dog Allowed | Outdoor Seating | W/D, Close to Beach & Village Shops
Beach nearby

Private Home | Dog Allowed | Outdoor Seating | W/D, Close to Beach & Village Shops

9.6 out of 10, Exceptional, (38)
"Trip was to help w family medical emergency- close to hospital but also to downtown, beaches etc. Perfect oasis from a stressful situation"
Private Home | Dog Allowed | Outdoor Seating | W/D, Close to Beach & Village Shops
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Terrace/patio

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

10.0 out of 10, Exceptional, (50)
"We loved our stay at Kayla's place! Everything was super clean when we walked in, and she clearly put a lot of thought into stocking up on all the little things you need but might forget to pack. The neighborhood was perfect - easy to get everywhere we wanted to go. Definitely worth booking if you're heading to the area."
The price is AU$535
includes taxes & fees
1 Dec - 2 Dec
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
New home 3/2 renovation 3 miles to Siesta Key
TV

New home 3/2 renovation 3 miles to Siesta Key

8.6 out of 10, Excellent, (4)
"The house was very clean with helpful amenities. However, the only complaint we have would be about the water pressure in the showers. Overall, it was a great experience in a great location, very close to the beach!"
The price is AU$526
includes taxes & fees
1 Dec - 2 Dec
New home 3/2 renovation 3 miles to Siesta Key
Downtown Escape! All new! Cute Villa in Sarasota!
Fridge, microwave, oven, stovetop

Downtown Escape! All new! Cute Villa in Sarasota!

9.8 out of 10, Exceptional, (6)
"The place was great and the neighborhood quiet. Our only problem was the washing machine which was indeed broken. When I was communication with the property manager they were so nonchalant about the probem. I know it was 7 am in the morning but we really needed the spin cycle to work to get the clothes dry. They wanted me to U-tube the issue and fix it myself. We ended up ringing the clothes out before drying them. It was just an unfortunate dilemma but we got through it."
The price is AU$393
includes taxes & fees
5 Dec - 6 Dec
Downtown Escape! All new! Cute Villa in Sarasota!
Unique Nokomis Home ~ 2 Mi to Beach Access!
Interior

Unique Nokomis Home ~ 2 Mi to Beach Access!

9.4 out of 10, Exceptional, (16)
"Nice place to stay. No issues. "
Unique Nokomis Home ~ 2 Mi to Beach Access!
Bright Venice Home w/ Yard < 4 Miles to Beach!
Outdoor dining

Bright Venice Home w/ Yard < 4 Miles to Beach!

10.0 out of 10, Exceptional, (19)
"We had a long weekend girls trip with our dogs this place was perfect. More then enough room and tons of amenities the pool was perfect "
Bright Venice Home w/ Yard < 4 Miles to Beach!
Comfortable 3-bedroom home with WiFi and AC in Englewood, close to many beaches.
Sun-loungers, beach towels

Comfortable 3-bedroom home with WiFi and AC in Englewood, close to many beaches.

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was amazing and it fit our party of 6 and the owner was great. "
Comfortable 3-bedroom home with WiFi and AC in Englewood, close to many beaches.
NEW Updated 3BR Robinhood Beach Villa near Siesta Key Beach! No hurricane damage
Fridge, microwave, oven, stovetop

NEW Updated 3BR Robinhood Beach Villa near Siesta Key Beach! No hurricane damage

2.0 star property
10.0 out of 10, Exceptional, (1)
"Close to Sarasota Memorial Hospital."
NEW Updated 3BR Robinhood Beach Villa near Siesta Key Beach! No hurricane damage
Charming 3-bedroom beach house in enchanting Sarasota only 8 minutes to Siesta
Fridge, microwave, oven, stovetop

Charming 3-bedroom beach house in enchanting Sarasota only 8 minutes to Siesta

2.0 star property
10.0 out of 10, Exceptional, (1)
Charming 3-bedroom beach house in enchanting Sarasota only 8 minutes to Siesta
Oceanfront home w/sunset views of Sarasota Bay
Fridge, microwave, oven, stovetop

Oceanfront home w/sunset views of Sarasota Bay

9.8 out of 10, Exceptional, (106)
"This house was perfect to visit our family.it was nice to have all the accommodations of home while being away from home. No problems at all with the home. Kids loved the pool more than the beach. The bay view with a full moon is breathtaking!"
Oceanfront home w/sunset views of Sarasota Bay
Sarasota-Indian Beach Zen Home (private-pet friendly)
Beach nearby, sun-loungers, beach towels

Sarasota-Indian Beach Zen Home (private-pet friendly)

9.8 out of 10, Exceptional, (24)
"We love everything about this property Even our 10 yo said that it’s her fav home "
Sarasota-Indian Beach Zen Home (private-pet friendly)
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Beach nearby, sun-loungers, beach towels

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

9.8 out of 10, Exceptional, (87)
"We loved our stay! Perfect location to walk to the beach, St. Armand’s circle, and the free trolley that takes you down town. We would stay again! Thank you"
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the 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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Other property types in Osprey

Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2074)
"Our suite was very clean and the hospitality was wonderful. Would definitely recommend to anyone. If we ever visit the area again we would definitely stay there."
The price is AU$266
includes taxes & fees
27 Nov - 28 Nov
Hibiscus Suites - Gateway to Siesta Key
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sports facility

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (211)
"Facility was great … would certainly stay here again in the future "
The price is AU$723
includes taxes & fees
4 Dec - 5 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club
Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
Tropical Beach Resorts
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.
Beautiful view of the beach with palm trees

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