Sarasota Vacation Rentals with Private Pool

(37 rentals)
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2 BR | 2 BA | Sleeps 6 | Quick View

$238

avg/night

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Key Amenities

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

About this property

MONTHLY/SEASONAL RENTAL! Welcome to Paradise. This completely updated and upgraded 6th floor, 1500 sq. ft. 2 bed/2 bath turnkey furnished condo and has beautiful downtown, and gulf views. Both bedrooms have King size beds. This tropical beach condo sleeps 6, and features a fold out sectional sofa, new ...

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Property Type

Sarasota Condo

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1 BR | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 2 miles to Lido

$250

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 apartment with gorgeous new inground swimming pool. Located in the wonderful Southside Village, also known as the Hillview Area. Walk to everything! Check out the rates tab for pricing information. We have 8 apartments in this little resort community. ...

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Property Type

Sarasota Apartment

"Great location with a pool!!!"

This was my second stay at one of Dee's rentals and they are fabulous!!! There is everything you could need and more. The pool being right there is a huge bonus as you don't have to head to the beach to ...

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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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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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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 BA | Sleeps 6 | Quick View

2

$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

"Peaceful setting!"

We just got done spending almost 2 weeks in this rental. We had the greatest time here. We were able to communicate with the owners, and they were just wonderful people. The pool wasn’t heated, but the ...

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Key Amenities

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

About this property

Welcome to Luna Nueva, a magnificent retreat that can be rented out separately or combined with its sister unit Villa Las Flores, to create Luna Flores. Whether you choose to rent them separately or together, this exceptional property promises an extraordinary vacation experience. With a private heated ...

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Property Type

Sarasota House

"Love the Pool and walking distance to stores and restaurants!"

This house was in perfect location for us. We come to Sarasota couple times a year. My brother lives in Sarasota few minutes away and the beach is the same distance so it was perfect for us. Having Walgreens ...

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Key Amenities

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

About this property

Welcome to Villa Las Flores, a magnificent retreat that can be rented out separately or combined with its sister unit Luna Nueva, to create Luna Flores. Whether you choose to rent them separately or together, this exceptional property promises an extraordinary vacation experience. With a private heated ...

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Property Type

Sarasota House

"Awsome time at Villa Las Flores"

My family and I had a wonderful time at the Villa Las Flores! The house was clean, accommodations were comfortable, and the self-checking-in was simple and easy. Restaurants, beaches, and shopping areas ...

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3 BR | 2 BA | Sleeps 8 | Quick View

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

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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
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Paradise Palms! This luxurious 4-bedroom/2.5-bathroom home is the paradise retreat you've been waiting for. It offers all of the amenities you could imagine for your most perfect Siesta Key vacation. Paradise Palms is just a short drive to Siesta Key Village and world famous Siesta Key ...

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Property Type

Sarasota House

"Indian Rock Beach Vacation"

GREAT Views / Great house on beach / Quiet Our family of 9 had a ball

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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

"Great location"

Only a couple blocks to the beach and super close to the main, commercial street, yet away from the noise and crowds. The apt was very basic, though clean with up to date furnishings. Smaller than I ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

1

Distance to beach: 3 miles to Siesta Key

$594

avg/night

View Details

Key Amenities

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

About this property

Welcome to Magnolia House, the ultimate vacation home for families. Single-level, 2,400 sq. ft home with 3 bed, 2.5 bath featuring king master suite with direct lanai access, split floor plan, queen bedroom with bathroom, and kids' room with 2 twin beds, and half bath. No design detail or amenity ...

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Property Type

Sarasota House

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1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 1 miles to Siesta Key

$142

avg/night

View Details

Key Amenities

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

About this property

\Virtual tour available upon request.May-November $1995 *6MONTHS PLUS NO TAX + SPECIAL RATE. December $3600 January-March $4500 April $3600 May-December $1995*Short-term rental taxes and fees will apply. *Calendar months only will be considered. *Ask ...

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Property Type

Sarasota Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

3

Distance to beach: 2 miles to Siesta Key beach

$142

avg/night

View Details

Key Amenities

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

About this property

This unit can accommodate up to 4 guest. Virtual Tour Available.May-Nov. $1995 *6 MONTHS PLUS NO TAX + SPECIAL RATE. December $3600 January- March $4500 April $3600 May-November 2024 $1995To make your stay even easier: Electricity, water, sewer, WI-FI trash and pest control will ...

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Property Type

Sarasota Condo

"Oasis on Osprey in Sarasota, Florida"

I stayed in a condo complex in Sarasota called Oasis on Osprey. The unit(s) was updated and the complex had a pool. It was a very spacious one bedroom on the ground floor with a screened in lanai and a ...

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 3 miles to Siesta Key Beach

$400

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

13

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

$140

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.Be Our Guest...very quiet, ...

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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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2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 5 miles to Siesta Key Beach

$446

avg/night

View Details

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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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 50 yards to Lido each

$292

avg/night

View Details

Key Amenities

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

About this property

Beautiful 1st floor condo directly on the Gulf of Mexico on a secluded section of Lido beach. Kitchen completely redone in 2023. Enjoy spending your day on the beach or pool just a few short steps from the condo's porch. Relax with your coffee in the morning enjoying the bright new day on the ...

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Property Type

Sarasota Condo

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4 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Siesta key

$534

avg/night

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Key Amenities

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

About this property

Luxury ranch home only a short drive to Siesta Key Beach, the #1 beach in the United States. Newly gut-renovated with attention to every detail. The house is located on Forest Lake Golf Course. We are located only a couple of miles from downtown Main Street, which is also one of the best places to visit ...

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Property Type

Sarasota House

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2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 1 miles to Crescent Beach

$358

avg/night

View Details

Key Amenities

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

About this property

Ideally located between Siesta Key and Sarasota. This home is exactly 1 mile from Crescent Beach. Close enough to enjoy everything Siesta Key has to offer but insulated from all the crowds, tourist traffic and noise. This home is extremely spacious for 2 bedroom/2 baths (almost 1,700 square feet!). The ...

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Property Type

Sarasota House

"My excellent Florida vacation"

The house we stayed at was excellent..It had all the amenities we could ask for..The hostess Lena was over the top when it came to taking care of whatever we needed she really went out of her way to make ...

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3 BR | 3 BA | Sleeps 8 | Quick View

1

$458

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 the nearest public beach access and less than 2 miles to the heart of Siesta Key ...

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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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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 sofaListing DesPlease note that the minimum lease period is (7) nights due to City Code restrictions. We are not able to make an exception. This fabulous canal-front home located on famous Lido Key, just minutes to St. Armand's ...

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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 | 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

4 Bedrooms, 4 Baths Sleeps 8 or at a discounted rate, a 3 bedroom 3 bath in the main house only. Please note that the minimum lease period is (7) nights due to City Code restrictions. We are not able to make an exception. The price listed is the main house only, which is a 3 bedroom 3 bath house without ...

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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

Master bedroom, with attached bathroom available in a fabulous pool home, tucked away on a quiet street near everything Sarasota offers. Minutes to Siesta Key, downtown Sarasota, hospital, restaurants, shopping, fitness and schools. Entertaining and seamless indoor/outdoor living from a large 17-by-37 ...

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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

1

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

"Lovely Condo next to Siesta Key!"

We thoroughly enjoyed our 4 month stay at this wonderful condo near beautiful Siesta Key! The condo was freshly updated, immaculately clean and is in a great location. We are within a few miles of both ...

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3 BR | 2 BA | Sleeps 8 | Quick View

$425

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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4 BR | 3 BA | Sleeps 8 | Quick View

$378

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

WELCOME TO A PIECE OF PARADISE JUST OFF SIESTA KEY. COME RELAX IN THIS BEAUTIFUL 4 BEDROOM / 3 BATH HOME THAT OFFERS TWO MASTER SUITES. LIGHT, BRIGHT and IMMACULATE HOME OFFERS GRANITE COUNTERTOPS, STAINLESS APPLIANCES WITH AN OPEN FLOOR. HIGH-SPEED INTERNET, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH ...

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Property Type

Sarasota House

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2 BR | 2 BA | Sleeps 4 | Quick View

$233

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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5 BR | 5 BA | Sleeps 8 | Quick View

Distance to beach: 0.1 miles to Lido

$699

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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$833

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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3 BR | 2.5 BA | Sleeps 12 | Quick View

$420

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

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 | 2.5 BA | Sleeps 7 | Quick View

$425

avg/night

View Details

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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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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4 BR | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 10 miles to Lido Beach

$351

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.4 bedroom. 4.5 bathroom. Sleeps 8.This beautiful 4 bedroom 4.5 bath home is spacious and expansive giving the feel of estate living. Open and bright with sliders off most of the rear of the house ...

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Property Type

Sarasota House

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3 BR | 3 BA | Sleeps 6 | Quick View

5.0 rating on other travel sites

$465

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Villa Serene Escape- Heated Saltwater Pool, Breathtaking Villa, outdoor terraces, and beautiful landscaping.The charm of the old with the modern look and style of the new! This one-of-a kind, 1925 home on a quiet West of Trail lane, was recently renovated and remodeled from top to bottom with exquisite ...

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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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Sarasota Vacation Rentals