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

Osprey Village Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Osprey Village vacation rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,931 reviews)
"Amazing resort,"
United States
kurt
The price is AED 496
AED 656 total
includes taxes & fees
4 Oct - 5 Oct
Tropical Beach Resorts
A compact living space with a kitchen, a dining area, and a sofa with cushions.

2. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is AED 231
AED 757 total
includes taxes & fees
8 Oct - 9 Oct
Tiny House Siesta
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,313 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is AED 573
AED 709 total
includes taxes & fees
8 Oct - 9 Oct
Captiva Beach Resort
An outdoor patio with a grill, white chairs, and a red umbrella.

4. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,456 reviews)
"This place was perfect!"
United States
Kat
The price is AED 460
AED 520 total
includes taxes & fees
26 Oct - 27 Oct
Hibiscus Suites - Gateway to Siesta Key
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

5. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
Siesta Key Island Rentals
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

6. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (186 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is AED 876
AED 990 total
includes taxes & fees
13 Oct - 14 Oct
SeaSpray Resort
A beach scene with a large sandcastle and people around it.

7. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is AED 364
AED 1,106 total
includes taxes & fees
4 Oct - 5 Oct
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A wooden structure with a thatched roof overlooking a beach.

8. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is AED 685
AED 843 total
includes taxes & fees
18 Oct - 19 Oct
Casey Key Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

9. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (686 reviews)
"Great stay!!"
United States
Genghis
The price is AED 694
AED 784 total
includes taxes & fees
4 Oct - 5 Oct
A Beach Retreat
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

10. [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)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is AED 375
AED 1,184 total
includes taxes & fees
4 Oct - 5 Oct
[lounge like locals] walk to siesta beach +bikes
Siesta Key Beach

11. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is AED 459
AED 1,270 total
includes taxes & fees
4 Oct - 5 Oct
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A beach with clear turquoise water and gentle waves.

12. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (54 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
The price is AED 472
AED 1,075 total
includes taxes & fees
4 Oct - 5 Oct
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A beach with clear blue water, gentle waves, and a distant sailboat.

13. Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (78 reviews)
"Great stay"
United States
Allison H.
Siesta Key Village-Suite #3: A Block to the Beach!
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

14. 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)
The price is AED 460
AED 1,414 total
includes taxes & fees
4 Oct - 5 Oct
Dolphin Villa - Pool - Steps to Siesta Key Village
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

15. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
A beach with a clear sky and calm sea.

16. Heart of Village: Dog-Friendly w/ Pool & Parking

Heart of Village: Dog-Friendly w/ Pool & Parking
Siesta Key Village
9.2 out of 10, Wonderful, (16 reviews)
"Love the place. Perfect location. Close to village, close to beach. Highly suggest and will definitely be back in the future. Host was very friendly and accommodating."
United States
Jeffrey B.
The price is AED 485
AED 1,400 total
includes taxes & fees
7 Oct - 8 Oct
Heart of Village: Dog-Friendly w/ Pool & Parking
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

17. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"The pool and proximity to the beach are great "
United States
Evan C.
Bright & Beachy–Beach Club Siesta Key 100A by RVA
A kitchen with a large window, a sink, a stove, and a chair.

18. Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾

Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾
Central Sarasota
9.6 out of 10, Exceptional, (75 reviews)
"Place was very nice and welcoming we will be back !!!!"
United States
Sue R.
The price is AED 437
AED 1,371 total
includes taxes & fees
19 Oct - 20 Oct
Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾
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.

19. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (93 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."
United States
Ashley H.
The price is AED 933
AED 2,237 total
includes taxes & fees
3 Oct - 4 Oct
Oceanfront home
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

20. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
8.8 out of 10, Excellent, (89 reviews)
"Great location and easy access to the beach."
United States
Erica B.
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
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 Village Hotel Reviews

Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

10/10 Excellent
"N/A"
Miguel 3-night trip
Posted 1 hour ago
Embassy Suites by Hilton Sarasota, FL

Frequently asked questions

Can I find a vacation rental in Osprey Village?

Yes, we give you a choice of vacation rentals close to popular local attractions in Osprey Village, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Osprey Village has to offer?

Tropical Villas of Venice Beach: This vacation home rental near Osprey Village is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals will I find in Osprey Village?

Expedia has 3 vacation rentals for your stay in Osprey Village.

What can I see and do in Osprey Village?

While exploring the area, visit family-friendly sights like Mote Marine Laboratory & Aquarium, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and Turtle Beach are a couple of places you'll find in the larger area.

What are vacation rentals like in Osprey Village?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Osprey Village. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.