Sarasota Vacation Rentals with Private Pool

(37 rentals)
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3 BR | 2.5 BA | Sleeps 7 | Quick View

$292

avg/night

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Key Amenities

  • Pet friendly
  • Private pool

About this property

Welcome to this beautiful remodeled 3 bedroom/ 2.5 bath home. This amazing location is just over the south bridge to Siesta Key's white powder beach, shopping, dining. With an oversized fenced-in backyard, it offers great privacy for those with a small dog. Beautiful new flooring, new kitchen/bathrooms, ...

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Property Type

Sarasota House

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Key Amenities

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

About this property

Welcome to 3180 Dividing Creek, a stunning rental property located in the beautiful city of Sarasota, Florida. This spacious home offers an ideal blend of comfort, style, and convenience, making it the perfect choice for your next getaway.Featuring 4 bedrooms and 2 bathrooms, this property provides ...

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Property Type

Sarasota House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Welcome to our exquisite waterfront retreat in the heart of Sarasota! This fully-stocked private home is a true gem, boasting 3 bedrooms, 2 baths, and a heated pool/spa. Prepare to immerse yourself in the ultimate indoor-outdoor living experience.Nestled in the upscale Southgate community, our tastefully ...

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Property Type

Sarasota House

"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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3 BR | 2.5 BA | Sleeps 6 | Quick View

3

Distance to beach: 3 miles to Siesta Key

$479

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Imagine a vacation home so thoughtfully designed and appointed that you don’t need to worry about a thing. Welcome to Magnolia House, hosted by me, Jen. Boasting a step-free, single-level home with an open floor plan that seamlessly blends indoor and outdoors with lots of natural sunlight. You are ...

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Property Type

Sarasota House

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3 BR | 2 BA | Sleeps 8 | Quick View

$292

avg/night

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Key Amenities

  • Pet friendly
  • Private pool

About this property

WELCOME TO A PIECE OF PARADISE! COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH HOME LOCATED IN THE QUIET NEIGHBORHOOD OF CORAL COVE. LIGHT, BRIGHT and IMMACULATE HOME OFFERS GRANITE COUNTERTOPS, STAINLESS APPLIANCES, OPEN FLOOR PLAN WITH ALL NEW FURNISHINGS.HIGH-SPEED INTERNET, (SIESTA 4 RENT IS NOT ...

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Property Type

Sarasota House

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3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 5 miles to Siesta Key

$285

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Charming old Florida home in a cul-de-sac backing to large palm and oak trees. Three bedrooms, two full baths. One outside shower. Quiet and quaint street. Freshley painted and new carpet through-out. All new beds and furniture. Two king bedrooms with dressers and smart TV's, wi-fi in place. One ...

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Property Type

Sarasota House

"Relax and recharge at Turtle Cove!"

Immaculate and spacious home with private pool, screened lanai, and modern applicances. Located in a quiet, centrally located Sarasota neighborhood within a short drive to great restaurants, Siesta Key, ...

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Brautiful Beach Front Condo on Gulf of Mexico
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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 50 yards to Lido Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

Beautiful ground floor condo directly on the Gulf of Mexico on a secluded section of Lido beach. No stairs or elevators to deal with! Kitchen, living area, and lanai completely redone in 2023.Enjoy spending your day on the beach or pool just a few short steps from the condo's porch. Relax ...

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Property Type

Sarasota Condo

"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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$500

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

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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Property Type

Sarasota House

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1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 2 miles to Lido

$135

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

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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Property Type

Sarasota Apartment

"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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3 BR | 2 BA | Sleeps 8 | Quick View

1

Distance to beach: 6 miles to Siesta Key Beach

Key Amenities

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

About this property

Welcome to Sarasota Florida. A premier: vacation, adventure, retirement destination. Located on the best (West) coast of FLORIDA. Creekview is located on Phillippi Creek in central Sarasota, approximately 5 miles from Siesta Key, the #1 beach in the world (2019). Spend time with family and friends at ...

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Property Type

Sarasota House

"I never stayed here!"

Looks great, but I have never been to Florida! If I am able to travel in the future, I would definitely book this property.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Casamigos, a rare upscale jewel in a sea of vacation rentals. This beautiful, newly furnished 4 Bedroom (all King Beds) /3BA home offers an exceptional vacation experience for your family and friends.It begins with lavish tropical landscaping (Malaysian and Areca Palms, Bougainvillea) and ...

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Property Type

Sarasota House

"Highly recommend this host"

Beautiful home. It was spotless when we arrived. All the beds and pillows were extremely comfortable. The Host was very accommodating to all our needs all week. Outside pool and Tiki Bar were a big hit ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Ocean Sky, a luxurious retreat that offers the perfect combination of comfort, convenience, and style. From the moment you step inside, you'll be greeted by a meticulously designed interior that caters to your every need.Ocean Sky features three spacious bedrooms and two full baths, ...

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Property Type

Sarasota House

"Wonderful house"

A beautiful home with everything that you can possibly need. The pool was outstanding since the temps were 90 degrees plus! The communication with the office was fantastic. Everything was provided for ...

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Key Amenities

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

About this property

This location is close to downtown Sarasota, which means minimal drive time to: arts, music, dining, shopping, fitness trails, fishing, beaches, sunning, sporting events, this pretty much describes the ideal Florida vacation! We are honored that you would consider our house for your vacation. Sarasota ...

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Property Type

Sarasota House

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Tropical Pool Home Near Siesta Key, Pet Friendly! POOL
Viewed

2 BR | 2 BA | Sleeps 4 | Quick View

13

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

$107

avg/night

View Details

Key Amenities

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

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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Property Type

Sarasota House

"Would Rent Here Again!"

Karyn and Steve were beyond attentive and available throughout the trip. The house was clean upon arrival and close to everything. Excellent location and very short drive to the beach. The neighbors were ...

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1 BR | 1 BA | Sleeps 4 | Quick View

4

Distance to beach: 2 miles to Siesta Key beach

$67

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

April-Nov. 2024 $1999 *6 MONTHS PLUS, NO TAX + SPECIAL RATE. December $3600 January- March $4500*Calendar months only will be considered. * Short-term rental tax will apply. *Pet Friendly, Private Yard, First Floor Unit. *Community pool and gym in Complex.This ...

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Property Type

Sarasota Condo

"Oasis on Osprey unit 107A"

Location,location...This condo was perfectly located for easy access to Siesta Key and downtown Sarasota as well as convenient walkable areas.All information and photos were exactly as described in the ...

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 3 miles to Siesta Key Beach

$395

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

*Multi-month discount is availableExperience the best of Sarasota at this beautifully decorated, wonderfully cared-for oasis featuring a large heated year-round saltwater pool and spacious screened-in outdoor living area. The home's split floor plan is perfect for two families. Americas ...

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Property Type

Sarasota House

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2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 1 miles to Siesta Key

$75

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

May-December 2024 $2,250 January-March 2025 $4500To make your stay more convenient we include electricity, water, sewer, wifi, and pest control.*Calendar months only. *Ask for our 6-month plus special rate * 6 Months + no short-term rental tax.This sunny and bright apartment ...

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Property Type

Sarasota Condo

"Pleasant Condo"

This one bedroom condo is in a great location to Siesta Key, downtown and many restaurants. It has a large living space and bedroom with a comfortable king bed. The backyard is a quiet and restful space. ...

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3 BR | 3 BA | Sleeps 8 | Quick View

1

$328

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Ideally located on the north end of Siesta Key, this charming resort-island home has loft-like spaces, a cool tropical modern vibe, plus 3 bedrooms, 3 baths and fantastic saltwater pool. This home is a 5 minute walk from a small public beach and less than 2 miles to the heart of Siesta Key Village. Close ...

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Property Type

Sarasota House

"Best Vacation ever"

The Pink Palm was amazing! Plenty of room and all the accommodations you could ever need. Loved the privacy of the pool. The beach was just a short drive away. Loved it and are considering returning again ...

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6 BR | 4.5 BA | Sleeps 12 | Quick View

3

$1100

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

This space offers 6 bedrooms (sleeps 16) 2 common areas (sleeps 4 on 2 rollaway beds and 1 double sleeper sofa bed), 4 full bathrooms, and a half bath. The abundance of natural Florida sunshine flows seamlessly throughout the home because of its many windows. Enjoy a sense of peace and tranquility throughout ...

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Property Type

Sarasota House

"Fantastic, 5 STARS"

Have rented this home twice in the last 3 months because it is outstanding. Traveled from MD to Sarasota with clients for golf and this is our go to rental. Hot tub, pool, several entertaining spaces ...

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2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 5 miles to Siesta Key Beach

$293

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Welcome to THE FUNKY FISH HOUSE, a luxurious and spacious vacation home located just minutes away from the #1 rated beach in the USA, Siesta Key. With its 2 bedrooms, an additional room with a twin day bed, and 2 full bathrooms, the house can comfortably sleep 5 guests with space for up to 6 total.The ...

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Property Type

Sarasota House

"Incredible time!"

I can’t say enough about how much we enjoyed our stay at the Funky Fish House! The house was everything they said it would be, and so much more. We are already making plans to book it again.

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3 BR | 3 BA | Sleeps 8 | Quick View

2

Distance to beach: 0.1 miles to Lido

$795

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

3 Bedroom 3.5 Bath, Sleeps 6 in beds, and 2 more on a pull-out sofaPlease note that the minimum lease period is (7) nights due to City Code restrictions. We are not able to make an exception.Also please note there is no parking on the street unless in a designated parking area. You will ...

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Property Type

Sarasota House

"Everything superb"

Lovely home! Spacious, spotlessly clean, all the supplies were well stocked and the kitchen had everything I needed, it was a pleasure to cook in. We will be booking again next year. Sue

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4 BR | 3 BA | Sleeps 8 | Quick View

$444

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

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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Property Type

Sarasota House

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2 BR | 2 BA | Sleeps 4 | Quick View

$83

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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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Property Type

Sarasota Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

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. You will love the fenced backyard featuring multiple seating areas and a pool to relax in. It is steps away from the world famous St. Armand's ...

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Property Type

Sarasota House

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4 BR | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 10 miles to Lido Beach

$500

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Minimum lease period (7) Nights due to County Code restrictions. We are not able to make an exception.There must be a minimum of (2) adults over the age of 30 as named tenants. We do not lease to young adults without adults over the age of 30 on the premisis.4 bedroom. 4.5 bathroom. Sleeps ...

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Property Type

Sarasota House

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4 BR | 3 BA | Sleeps 8 | Quick View

$365

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Bird Key canal front ParadiseWelcome to waterfront living on one of the most desirable streets in Bird Key. A circular paver drive enveloped by lush mature landscaping frames the façade, as a double-door entry leads the way inside to its spacious and open floorplan with high ceilings in living ...

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Property Type

Sarasota House

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Key Amenities

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

About this property

Recently updated and situated in the highly sought-after Gulf Gate community, this 2 bed/2 full bath Sarasota home with heated and caged pool is designed with a relaxing stay in mind. Just 4.5 miles away from Siesta Key Beach (voted #1 beach in the US), 1 mile away from Gulf Gate Shopping and Dining ...

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Property Type

Sarasota House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Turnkey Furnished Short Term Rental. Welcome home to this 2 bedroom,2 bathroom unit located in Carrington Place with its Heated Pool,Covered Parking,and Elevators. This slice of paradise sits in an incredible location. Only Minutes from Palmer Ranch. This coveted 3rd floor unit boasts a picture-perfect ...

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Property Type

Sarasota Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Beautiful golf course views from this Palmaire Fairway Lakes 3 Bedroom 2 Bath Furnished home! Heated Pool, 2 Car Garage. King in Master Bedroom with walk in shower, soaking tub and large walk in closet. Queen Beds in 2 Guest Bedrooms. Fairway Lakes is located just a short golf cart ride away from the ...

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Property Type

Sarasota House

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Key Amenities

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

About this property

Minutes to Siesta Key, downtown Sarasota, hospital, restaurants, shopping, fitness and schools. Entertaining and seamless indoor/outdoor living from a large 17-by-37 resort-style pool with fountains, an alcove with a built-in table and seating is incredible, tranquil and relaxing. There is a hard-to-find ...

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Property Type

Sarasota House

"Wonderful home - great pool - close to beaches!"

Owners Rachael & Sarab were wonderful during our stay and great to work with. The pool was as advertised, very large, great for a good sized family with kids. The home layout was great for our family as ...

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Crescent Beach

$250

avg/night

View Details

Key Amenities

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

About this property

This gorgeous 1940’s bungalow style secluded beach hideaway with your own private pool and jacuzzi is the perfect escape! Treat yourself to a peaceful and relaxing vacation that's just a 4-minute drive or a short 6 block walk from world famous Siesta Key Beach! Hosts provide beach towels, ...

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Property Type

Sarasota Bungalow

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3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 2 miles to Cresent Beach

$250

avg/night

View Details

Key Amenities

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

About this property

Florida living at its best… just MINUTES to the beaches of SIESTA KEY!NOT YOUR TYPICAL RENTAL. The minute you walk in the door you will fall in love with the oversized living room with vaulted ceilings and white porcelain floors that shine throughout the entire home. A pair of 7 ft sliders ...

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Property Type

Sarasota House

"Our extended stay in your beautiful home."

This home is in a well located, quiet location near Siesta Key Beach. We loved how clean and spacious it is. The home has such an inviting and cozy feel to it. The pool was a nice touch. The homeowners ...

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4 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 0.1 miles to Lido

$995

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This price includes both the main and guest house. With both, it is 4 Bedrooms, 4 Baths that sleeps 8 or at a discounted rate, a 3 bedroom 3 bath in the main house only. The apartment has a separate fully equipped kitchen, living room and full size stacked washer/dryer laundry closet)Please note ...

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Property Type

Sarasota House

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5 BR | 5 BA | Sleeps 8 | Quick View

Distance to beach: 0.1 miles to Lido

$800

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

125S - 5 Bedroom 5.5 Bath Sleeps 10 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, ...

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Property Type

Sarasota House

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Two bedroom, two full bathroom, newly remodeled condo west of the Tamiami Trail.
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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 3 miles to Siesta Key

$90

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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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Property Type

Sarasota Condo

"A Great Experience"

Location is everything and this condo has it!! Minutes from Siesta Key's powder sand beach and so close to everything that Sarasota has to offer. This recently upgraded unit is exceptionally clean and ...

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3 BR | 2.5 BA | Sleeps 12 | Quick View

$230

avg/night

View Details

Key Amenities

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

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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Property Type

Sarasota House

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3 BR | 3.5 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Siesta Key Beach

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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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Property Type

Sarasota House

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Sarasota Vacation Rentals