Osprey Village Vacation Rentals

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Our top choices for Osprey Village vacation rentals

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (22 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
$135 nightly
The price is $150
Apr 12 - Apr 13
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (269 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
$127 nightly
The price is $143
May 4 - May 5
Total with taxes and fees
Kon Tiki Inn

Coastal Quadruplex with private beach access & deck - dog-friendly

Coastal Quadruplex with private beach access & deck - dog-friendly
Manasota Key
8.2 out of 10, Very Good, (17 reviews)
"Great place to stay. "
United States
Scott
$344 nightly
The price is $381
Apr 12 - Apr 13
Total with taxes and fees
Coastal Quadruplex with private beach access & deck - dog-friendly

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (21 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
$202 nightly
The price is $225
Apr 16 - Apr 17
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
$251 nightly
The price is $280
May 1 - May 2
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (37 reviews)
"Me and my significant other took a little mini vacation wonderful house. It was very clean very beautiful inside, I like the beach vibes beautiful bedrooms. I recommend anybody to book this place. If I had to go back, I’ll book again. "
United States
Alexus
$292 nightly
The price is $326
Apr 12 - Apr 13
Total with taxes and fees
Mimosa Memories

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, (73 reviews)
"Wonderful Stay"
United States
Christopher R.
$236 nightly
The price is $263
Apr 13 - Apr 14
Total with taxes and fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Newly renovated only minutes away from the beach!!

Newly renovated only minutes away from the beach!!
Olde Englewood Village
9.6 out of 10, Exceptional, (63 reviews)
"Clean, comfortable, everything you need! Owner is great!"
United States
Cheryl L.
$256 nightly
The price is $285
Apr 14 - Apr 15
Total with taxes and fees
Newly renovated only minutes away from the beach!!

Path to Paradise.

Path to Paradise.
Olde Englewood Village
$271 nightly
The price is $303
Apr 18 - Apr 19
Total with taxes and fees
Path to Paradise.

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
$459 nightly
The price is $479
Apr 19 - Apr 20
Total with taxes and fees
Beachy Sarasota Duplex

Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (113 reviews)
"Beach view with sunset!!"
United States
joseph l.
Sunset and beach view from your balcony Unit 403

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

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Lido Key
9.8 out of 10, Exceptional, (122 reviews)
"Super clean, perfect location, and cool decor - and, most important, veeerry comfortable beds! We loved our stay! "
United States
Kevin L.
$255 nightly
The price is $285
Apr 23 - Apr 24
Total with taxes and fees
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · 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.
$379 nightly
The price is $379
Apr 14 - Apr 15
Total with taxes and fees
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,228 reviews)
"Clean and very close to beach. "
United States
Daniel
$251 nightly
The price is $281
Apr 12 - Apr 13
Total with taxes and fees
Captiva Beach Resort

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (23 reviews)
"Fun place "
United States
Maureen
$225 nightly
The price is $252
May 7 - May 8
Total with taxes and fees
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
$349 nightly
The price is $357
Apr 13 - Apr 14
Total with taxes and fees
[escape to paradise] siesta key beach getaway

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
8.6 out of 10, Excellent, (14 reviews)
"Great locale right on the beach "
United States
Carole
$319 nightly
The price is $355
Apr 17 - Apr 18
Total with taxes and fees
Beachfront Bliss on Longboat Key- Steps to the sand

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (40 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
$185 nightly
The price is $207
Apr 28 - Apr 29
Total with taxes and fees
Beautiful University Pines Studio in Sarasota

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (106 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
$309 nightly
The price is $349
May 4 - May 5
Total with taxes and fees
SeaSpray Resort

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
$426 nightly
The price is $475
Apr 12 - Apr 13
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
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

Find out more about Osprey Village

Everything you need to know about Osprey Village vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey Village vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey Village vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey Village vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey Village. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osprey Village in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osprey Village rentals

At Expedia, we put the best Osprey Village vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osprey Village rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey Village vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey Village. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Osprey Village?

Yes, we give you a choice of vacation rentals in Osprey Village close to Nancy's Consignments, or you can go with a more remote option if you're looking for extra privacy while you relax.

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

Siesta Key Island Rentals: This vacation home rental near Osprey Village comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

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 Nancy's Consignments, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and Jim Neville Marine Preserve 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.