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Sarasota Vacation Rentals with Private Pool

(39 rentals)
Sarasota House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your private waterfront paradise in the heart of Sarasota! This beautifully designed 3-bedroom, 2-bathroom retreat offers the perfect blend of luxury, comfort, and serene natural surroundings. With a heated pool and spa, this home is fully stocked to provide you with the ultimate indoor-outdoor...

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Featured review

"Great Place"

There were only 2 of us and we had this huge house to ourselves. This is a family-friendly "home" with a large open kitchen/dining/family room area, lots of open space, and a great screened in outdoor...

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$379
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 1 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

OUR RATES:June-November 2025 $2250 December 2025 $3000 January 2026 $4500 February 2026 $5000 March 2026 $5000 April 2026 $3000 May-December 2026 $2250*Calendar...

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Featured review

"Great stay at Oasis on Osprey"

It was a pleasure working with Ana (and her husband). The unit was clean, modernized, and comfortable. The area was very nice, quiet, friendly neighbors and kept clean. Location was good, plenty of restaurants...

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$145
avg per night
Sarasota House
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

WE’REOPEN ,NO DAMAGE TO UNITa small studio condo: a fairly private bedroom (no door) and a sleeper sofa in the living room; best for 2, but sleeps 4. There is a very small screened balcony. The one bath has a shower. The guest section of the closet has hanging space, several shelves and drawers;...

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$126
avg per night
Sarasota House
Sleeps 12, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Very nice & Spacious 3 bedms/2.5bathms home with heated swimming-pool in Euclid Ave. Near beaches (15min) and downtown (5min) and Shopping St Armand Cir (15 min). Perfect for family and friends. Modern comfort renovated with a large garden Near to Yoder's Fresh market and Arlington park (playing...

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Sarasota House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

NO DAMAGE AFTER HURRICANE Located in the heart of Sarasota, less than ten minutes to Siesta Key Beach and Downtown Sarasota, completely renovated home has it all. Ranch style has tall ceilings, modern kitchen, open layout. Four bedrooms to choose from . A spacious master bedroom and a spa like bathroom...

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$344
avg per night

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Sarasota House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

OPEN FOR RENT AFTER HURRICANE You'll really enjoy this vacation home. This very spacious 3 bedroom, 2 bath home has plenty of room in the living, dining, and pool deck . This recently renovated ranch style is in one of the most desirable locations in Sarasota! Nestled in the quaint area of Gulf Gate....

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$298
avg per night
Sarasota House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Very inviting home with pool, fenced yard and simple walk to St Armand's Circle.A Jewel on St. Armands Circle! The location makes this spacious 3BR+Casita/3BA with a private pool in a botanical setting a perfect month long vacation spot. This residence has it all for those who want to be right...

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$796
avg per night
Sarasota Apartment
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

Distance to beach: 2 miles to Lido

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Relax at this lovely comfortable and spacious one bedroom or studio apartments with gorgeous new inground swimming pool at the Southside Village Resort. Check out our website for all the various options that are available. We are located in the wonderful Southside Village, also known as the Hillview...

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Featured review

"2 week holiday"

Fantastic. Like home away from home. great Hosts and beautifully located. Flat was sparkling clean and jason and Dee and their son Storm always on hand for any help required. We can only highly reccomend...

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$187
avg per night
Sarasota House
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Bring the whole family as this home features 3 bedrooms and 2 1/2 baths. This very spacious home is almost 2,600 square feet with plenty of room to relax. Huge open living area. You will love the fenced backyard featuring multiple seating areas and a pool to relax in. Portable putting green and safe ax...

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$827
avg per night
Sarasota House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Check-in time: 16:00 Check-out time: 10:00 Early Week Discount 15: 15.00% (for stays between 3 and 27 nights)

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$405
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

A Great Home Away from Home Boatyard Gated Community Comfy Lanai for relaxing and entertaining Bamboo Wood Floors 2 bedrooms (one king and one queen bed) and 2 bathrooms Heated Pool Upgraded features include new paint and wonderful main bedroom walk in shower Wonderful fishing with several...

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$285
avg per night
Sarasota House
Sleeps 10, 4 bedrooms, 2 bathrooms

Distance to beach: 10 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Bradenton Paradise 4BR/2BA HEATED POOL & Mini Putt Welcome to your Bradenton retreat, a spacious 4-bedroom, 2-bathroom home designed for comfort, fun, and family gatherings. Sleeping up to 10 guests, this beautifully maintained property offers modern amenities and a bright, open layout perfect for...

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$149
avg per night
Sarasota Studio
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

WE ARE OPEN AFTER HURRICAN IAN Steps to the beach, restaurants and dining, family-friendly activities, and public transport. This is a 2016 remodel. Great for kayaking and biking. Walking or biking distance to Lido Beach, St. Armand's Circle and Ted Sperling Kayak Park. The one room studio is good...

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$119
avg per night
Sarasota Studio
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Recently renovated studio apartment located on short walk to Lido Key Beach and St Armand's Circle. Building was painted blue November 2023.The space Studio apartment or some may call it an efficiency. It has a full kitchen full bath, laundry inside.It has a king size bed. Also has an outside...

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$128
avg per night
Sarasota House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

WE ARE OPEN . No damage to unit. Brought to you by Pier Property Management. Get ready to immerse yourself in the coastal vibe and everything the gulf beaches have to offer. This charming 1/2-acre home located in one of Sarasota's most desirable communities features 4 bedrooms, 3 full baths and...

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$302
avg per night
Sarasota House
Sleeps 8, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Located in a quiet cul-de-sac, this property offers a peaceful and tranquil setting. Away from the hustle and bustle of the city, you can enjoy a serene and calm environment in your own home.The private lanai with a saltwater pool provides a secluded outdoor space where you can relax and unwind. Whether...

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Featured review

"Great house,great location,great value."

We have vacationed in Sarasota for several years and this property was one of the best of our stays.All the conviences of home,and then some,great location,and a terrific value.

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$328
avg per night
New
Sarasota Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

*Sorry for picture quality, new pictures coming soon. Please ask and I can send better pictures* Recently purchased, so not many reviews yet, but villa is all new and cozy. Discover this amazing 2-bedroom gem in Siesta Key Jamaica Royale is a gulf side paradise. Jamaica Royale offers 300 feet of private...

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$360
avg per night
Sarasota House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Turnkey furnished home, 3 bedrooms, 2 bathrooms, 2 car garage, king bed in master bedroom with walk-in shower, soaking tub and large walk-in closet. Queen beds in the 2 guest rooms. Heated private pool.

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$833
avg per night
New
Sarasota House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Enjoy a homey Florida bungalow with wood floors and natural light in a quiet neighborhood moments from downtown. Included is a spacious and private, fenced-in backyard with pool, covered grill and eating area. The main bedroom has a king-sized bed with en-suite bathroom and walk in closet; guest bedroom...

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Sarasota Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 50 yards to Lido Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our stunning ground floor condo, nestled directly on the pristine Gulf of America along a tranquil stretch of Lido Beach. Say goodbye to stairs and elevators – step right into your paradise!Completely renovated in 2025, this condo offers a fresh and modern retreat, designed with...

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Featured review

"Absolutely Wonderful"

We rented this gorgeous Condo for the month of March, 2024. First of all, the location is perfect, right on Lido Beach with a pool onsite and right down the street from St. Armand's Circle in Sarasota....

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$333
avg per night
Sarasota House
Sleeps 10, 4 bedrooms, 2 bathrooms
40 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

This holiday, give the gift that builds memories and strengthens bonds. Enjoy peaceful mornings by the creek- feel the refreshing breeze while listening to the birds who call it home. Nearby UTC sparkles with holiday lights-music, activities, shopping, carriage rides, and so much more. Back home, unwind...

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Featured review

"Met our expectations."

We were located near the airport and the beaches. We would drive to the beach areas and get on the free trolleys to explore the various parts of the city and islands, or enjoy the sunny weather on the...

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$406
avg per night
Sarasota Condo
Sleeps 4, 1 bedroom, 1 bathroom
6 reviews

Distance to beach: 2 miles to Siesta Key beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

OUR RATES:June-November $1999 December $3000 January $3900 February-March $4500 April $2500 May-December $1999*Calendar months only. *Pet Friendly, Private Yard, First Floor Unit. *Community pool and gym...

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Featured review

"1 Bed/1 Bath Oasis on Osprey"

We stayed here for a clinical rotation from July - October at the Oasis on Osprey. It was truly a wonderful experience. Ana was always so helpful and attentive whenever we needed something. The area surrounding...

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$131
avg per night
Sarasota House
Sleeps 4, 2 bedrooms, 2 bathrooms
15 reviews

Distance to beach: 2 miles to Siesta Key Beach / Cresant Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Quiet, private and pet friendly 2 bedroom, 2 bath, swimming pool home in Gulf Gate just 5 minutes to Siesta Key and her Beaches! Your Rental Fee includes the following (Rent, Cleaning Fee, Florida 12% taxes, Cable, Water & Utilities). Pet Fee additional to rental fee. NO Owners or Service Fees,...

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Featured review

"Enjoyed stay"

Stayed here 3 weeks in November, the house was clean and well supplied with all you could need. The pool was great and the owners were very enjoyable to deal with. The only draw back I could see was myself...

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$149
avg per night
New
Sarasota House
Sleeps 14, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool

About this property

Seascape on Clarinda | Spacious 4BR/4BA Private Pool Home with Outdoor Kitchen & Beach GearWelcome to Seascape on Clarinda, a stunning full-house rental nestled in Sarasota, Florida, just 20 minutes from the world-famous Siesta Key Beach. This beautifully appointed 4-bedroom, 4-bathroom home comfortably...

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$548
avg per night
Sarasota House
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Fantastic totally remodeled vacation spot with a luxurious screened in private heated pool - this spacious house has all the amenities of home so you'll never want to leave! Just a quick 7-10 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St...

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$329
avg per night
Sarasota House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Beautifully renovated and immaculate home with pool and dock Near St Armand's and Lido BeachNEW PROPERTYWelcome to 440 Cleveland Drive, a stunning, fully renovated rental property on Lido Key where luxury meets coastal charm. Completed in March 2025, everything inside and outside this home...

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$1,845
avg per night
Sarasota House
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Longboat Key

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for...

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$377
avg per night
Sarasota House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Escape to your own slice of paradise in the heart of Sarasota's coveted Gulf Gate community with this beautifully updated 2-bedroom, 2-bathroom retreat, designed with a relaxing stay in mind. Featuring a heated, caged pool, and just moments away from the world-renowned Siesta Key Beach, this gem...

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$215
avg per night
Sarasota Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

My wife and I are recently retired educators. We ARE NOT multiple rental property owners. We own this one condo and are snowbirds from Pennsylvania. Our place is newly remodeled floor to ceiling! The Oasis complex is a prime location in close proximity to downtown Sarasota, Siesta Village, & nationally...

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Featured review

"Very nice condo"

Convenient location minutes from the beach, shopping and entertainment. Our host was very helpful and the condo was well equipped. Would stay again. No washer and dryer was a bit inconvenient but laundry...

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$90
avg per night
Sarasota House
Sleeps 12, 5 bedrooms, 5 bathrooms
6 reviews

Distance to beach: 0.1 miles to Lido

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Lovely remodeled and refurbished 5 bedroom 5.5 bath pool home on desirable St. Armand's Circle! This 3,000 s.f. home comfortably sleeps (8) in beds, and has T.V.'s in the family room and living room for when the family is not enjoying the caged pool and spa. Professionally decorated, quality...

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$800
avg per night
Sarasota House
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

A Florida style charming paradise cottage featuring a tropical oasis backyard with large in-ground pool and bar area. This home is fully furnished and conveniently located. Enjoy a newly renovated home that includes an updated kitchen, living room, bathroom and bedrooms, and new central air and roof....

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Featured review

"A bit of heaven on earth"

Clean, comfortable, private, convenient! The private yard and sweet making pool are spectacular. Owner responsive. Our favorite place!!! Worth every cent!!!

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$134
avg per night
Sarasota House
Sleeps 14, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Glamor Manor, your luxurious retreat in the heart of Sarasota, Florida! This exquisite vacation rental offers an unparalleled experience of comfort, style, and relaxation.Property Highlights: Pet friendly : $200 non-refundable pet fee Heated Swimming Pool: Dive into luxury with our private...

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$1,044
avg per night
Sarasota House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 4 miles to Siesta Key/Crescent Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This exquisite Coastal House with all brand NEW furnishings has a beachy style with King size beds in ALL 3 bedrooms! It’s conveniently located just 3.8 miles from #1 Siesta Key Beach, only 5 miles to downtown Sarasota, just 7.5 miles to Lido Key Beach/St. Armand's Circle, 2 houses down from...

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Featured review

"Newly Remodeled, Super Clean!"

We had a lovely stay at this newly remodeled home in Sarasota. We enjoyed morning coffee on the back patio after a great night's rest in the king size beds (three KING beds--what a bonus!), and we definitely...

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$325
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Contact: Erana Pulli or Joesgirl16@ Newly renovated condo. First-floor end unit with a beautiful, private courtyard. Large, light, bright, and airy best describes our home! Granite countertops and stainless steel appliances are found in our eat-in kitchen. Another large dining table off the living area....

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$159
avg per night
Sarasota House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to your dream vacation home in Sarasota! This exceptional 3-bedroom, 2.5-bath house in the peaceful Coral Cove neighborhood offers a perfect blend of comfort and convenience. Relax by the private pool, enjoy the open floor plan with granite countertops, stainless steel appliances, and new furnishings....

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$299
avg per night
Sarasota House
Sleeps 10, 4 bedrooms, 3 bathrooms

Distance to beach: 8 miles to Lido Key

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Saltwater Siesta — a family favorite near IMG Academy and the Gulf’s white-sand beaches! Lounge by the heated saltwater pool (no heating fee), or head to the epic game room for endless fun with arcade games, ping pong, and foosball. Cook up gourmet meals in the full equipped kitchen....

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$467
avg per night
Sarasota House
Sleeps 8, 4 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.1 miles to Lido

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

St. Armand's Canal-Front Pool Home steps to the beach!This gem, ranch style home estate has been completely rebuilt and remodeled in 2015 from the frame including all new finishes inside and out. With fresh, coastal Old-Florida decor, it is in one of the most desirable locations on the west...

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$1,117
avg per night
Sarasota Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Direct beachfront condo located on the desirable Crescent Beach at the southern end of Siesta Key. Views for miles of the sparkling gulf waters, white sand and Point of Rocks from all rooms. An open and spacious floor plan, generous balconies, washer/dryer in the condo. Covered parking and elevators all...

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$672
avg per night
Sarasota House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Distance to beach: 7 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Luxury lakefront home on a quiet cul de sac located in pristine Palmer Ranch. Kick back on the covered front porch and relax in the glider and rocking chairs. Soak up some sun in the screened in lanai with heated saltwater pool overlooking the lake. Enjoy community amenities such as the clubhouse, lighted...

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$306
avg per night
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