Sarasota Vacation Rentals with Private Pool

(34 rentals)
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3 BR | 3 BA | Sleeps 4 | Quick View

$1000

avg/night

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Key Amenities

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

About this property

Welcome to charming, old Florida! Super centrally located on a peninsular with water views both sides of the house, this single family home is perfect for any mood. Relax at your private pool, Walk or Cycle to Siesta Key, Kayak or Paddleboard to the bird islands, Fish off the dock, Wade off the fishing ...

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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

This inviting 3-bedroom/two-bath vacation rental home has everything for your most memorable Siesta Key vacation! Luna Nueva is centrally located near downtown Sarasota and just a short drive to world famous Siesta Key Beach, voted the #1 beach in the USA! Along with its sister property Villa Las Flores, ...

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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
  • 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 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

$436

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This luxurious and recently renovated 3-bedroom/2-bathroom home is located in close proximity to Siesta Key Village and just minutes to Siesta Key Beach, voted the #1 beach in the USA! Immaculately decorated and with your every comfort in mind, you will truly be living a life of luxury right here on Siesta ...

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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

This inviting 3 bedroom/2 bathroom home features a private heated pool and is centrally located near downtown Sarasota. With just a short drive to world famous Siesta Key Beach, you will truly be living the Florida Life! Villa Las Flores is the ideal home for small families and couples looking for a tropical ...

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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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1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Siesta Key beach

$145

avg/night

View Details

Key Amenities

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

About this property

Rent Information:May-November $2400 December $2400 January- March $5000 per month April $35003D tour available upon request.This condo will accommodate up to 4 people, most comfortable for a couple. Ask for special rates for 3 months or more. ***Pet Friendly, please call for more details.*** *Short ...

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Property Type

Sarasota Condo

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6 BR | 4.5 BA | Sleeps 12 | Quick View

2

$1126

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 12), 2 common areas (sleeps 4), 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 this uniquely charming and stylish house. ...

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Property Type

Sarasota House

"Truly tranquility at this spacious home!!,"

We really enjoyed our time at spacious 5 bedroom home each with its own bathroom. Michael, Claudine and their local representative Dazery are great communicators. It has all the goodies pool large entertainment ...

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4 BR | 4 BA | Sleeps 10 | Quick View

5.0 rating on other travel sites

$800

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This astonishing 4 bedroom/ 4 bathroom home offers everything you will need for the most memorable Siesta Key beach vacation at an unbeatable location. Enjoy a spacious and exquisitely decorated interior or relax in your very own backyard oasis with a private heated pool facing the intracoastal waterway. ...

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Property Type

Sarasota House

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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 Beach, ...

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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

This colorful and vibrant Siesta Key home features gorgeous panoramic views of the Gulf of Mexico and offers all of the amenities you could dream of for your beach vacation and an unbeatable location! Crystal Sands is located minutes away from Siesta Key Village and just a 1 minute walk to world famous ...

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Property Type

Sarasota House

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4 BR | 4 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$413

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Manatee Cove! This private family Lido Key home is perfect for families, with the ability to accommodate up to time 8 guests, with 4 bedrooms and 4 bathrooms. This waterfront home offers all of the amenities you could dream of for your beach vacation and an unbeatable location. Manatee Cove ...

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Property Type

Sarasota House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This coastal 3 bedroom/ 3 bathroom home features all the amenities you can think of for your beach vacation and offers an unbeatable location that is walking distance to Siesta Key Beach and Village.Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With ...

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Property Type

Sarasota House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Introducing Gulf Birdie! This serene 3 bedroom 2 bathroom waterfront home is perfect for your family vacation. Not only does it include a spacious heated luxury pool and hot tub, but it also sits directly on the canal. Whether you choose to catch up on your favorite book poolside, take in the beautiful ...

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Property Type

Sarasota House

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3 BR | 2 BA | Sleeps 8 | Quick View

4.5 rating on other travel sites

$160

avg/night

View Details

Key Amenities

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

About this property

This luxurious and recently renovated 3-bedroom/2-bathroom home is located in the heart of Sarasota with close proximity to downtown Sarasota, Siesta Key Village, and Siesta Key Beach, voted the #1 beach in the USA! With so much to do in the area and a private pool, you will truly be living a life of ...

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Property Type

Sarasota House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This colorful and vibrant Siesta Key home features gorgeous panoramic views of the Gulf of Mexico and offers all of the amenities you could dream of for your beach vacation and an unbeatable location! Silver Shore is located minutes away from Siesta Key Village and just a 1 minute walk to world famous ...

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Property Type

Sarasota House

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3 BR | 2 BA | Sleeps 8 | Quick View

4.8 rating on other travel sites

$175

avg/night

View Details

Key Amenities

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

About this property

Introducing Casa Tortuga! This private 3 bedroom / 2 bathroom family home has everything you need to relax on your most memorable Siesta Key vacation! It is centrally located near downtown Sarasota and just a short drive to Siesta Key Beach, voted the #1 beach in the USA. From relaxing by the private ...

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Property Type

Sarasota House

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$229

avg/night

View Details

Key Amenities

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

About this property

Great house in Sarasota only 5 min to Siesta key beach. Close to resturants and publix. 4 bedroom with 2 bathrooms with private heated pool. Big private backyard. Pets are welcome to. Nice and quiet area. Welcome!

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Property Type

Sarasota House

"Great time"

Hello, Just want to let you know that our stay at you home this week was far beyond great. The house was just perfect. This was a much needed vacation. Thank you so very much. My family would love to use ...

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 50 yards to Lido each

$200

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. 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 screened in porch. Minutes from outstanding ...

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Property Type

Sarasota Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

11

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

$132

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). THERE ARE NO OWNERS FEES OR SERVICE FEES.Be Our Guest...very ...

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Property Type

Sarasota House

"Wonderful Vacation Home"

We really enjoyed our stay at the Hewett's home on our May vacation to Sarasota. The home and pool were so relaxing with everything we needed to make our stay enjoyable, The residents at the gulf gate ...

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 5 miles to Lido Key

$200

avg/night

View Details

Key Amenities

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

About this property

Our home is a comfortable and nicely decorated three bedroom and two bath home with a heated pool located only one mile from downtown Sarasota and 5 miles to Lido Beach. Additionally we are located close to several museums and a miniature golf course as well as nearly 40 restaurants within 5 miles. ...

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Property Type

Sarasota House

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3 BR | 2 BA | Sleeps 5 | Quick View

1

Distance to beach: 2 miles to crescent beach

$315

avg/night

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Key Amenities

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

About this property

MyHome Florida is a single-family home with a heated private salt water pool just 4 miles to the #1 beach in the USA, Siesta Key Beach and just over 2 miles to Crescent Beach. It offers 3 bedrooms, 2 bath with a screened backyard . The fully private, fully enclosed outdoor space is one-of-a-kind with ...

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Property Type

Sarasota House

"Wonderful stay, great amenities and loved the location"

This place was quite the treat! It was better than expected. Place is completely renovated. Pictures are accurate and the place is very clean.We really enjoyed our stay here. The house is very well ...

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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 1 miles to Crescent Beach

$331

avg/night

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Key Amenities

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

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

"Welcoming House, Amazing location"

Loved it. Amazing house and the pool was awesome. Location was great and the yard is big. Thank you would love to come again

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3 BR | 3 BA | Sleeps 8 | Quick View

$520

avg/night

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Key Amenities

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

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

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2 BR | 2 BA | Sleeps 4 | Quick View

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Private pool

About this property

Welcome to our “Island Paradise” located on the world famous white sand Crescent Beach on Siesta Key. The coastal décor and incredible gulf view has everything you need for a comfortable and relaxing restful vacation in paradise. This beautiful 2 bedroom, 2 bath condo has recently been ...

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Property Type

Sarasota Condo

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3 BR | 3 BA | Sleeps 8 | Quick View

1

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 Circle ...

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Property Type

Sarasota House

"Awesome location: Awesome home layout"

This house is wonderful. Location and layout of the home are even better. Twin beds, in one room however, are definitely for kids (who don’t care about comfort). Unfortunately we had adults in those ...

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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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4 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 - 4 Bedrooms, 4.5 Baths (Sleeps 8) Lovely remodeled and refurbished 4 bedroom 4.5 bath pool home on desireable 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, or ...

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Property Type

Sarasota House

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3 BR | 2 BA | Sleeps 8 | Quick View

$419

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 | 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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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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3 BR | 2.5 BA | Sleeps 7 | Quick View

$419

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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4 BR | 5.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.1 miles to Lido Beach

$1851

avg/night

View Details

Key Amenities

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

About this property

Luxury, location, and the ultimate private resort-style living, welcome to 211 Tremont Lane. A rare opportunity to rent on the only private street on the sought-after St. Armands Key. Only a short walk to the renowned dining and shopping area on St. Armands Circle or a short walk to the beach. This home, ...

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Property Type

Sarasota House

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3 BR | 2 BA | Sleeps 6 | Quick View

$285

avg/night

View Details

Key Amenities

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

About this property

Charming old Florida home in a cul-de-sac backing to large palm trees. Quiet and quaint street. Freshley painted and new carpet through-out. All new beds and Funiture. 2 King beds with dressers and TV's cable and wi-fi in place. All smart TV's. One queen no TV. Charming original kitchen with newer appliances ...

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Property Type

Sarasota House

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Key Amenities

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

About this property

Legacy FL Beach Cottage, 3rd house from Beach Path on Exclusive Prime N. Lido Beach. This is a rare find in a nice quiet neighborhood, steps away from spectacular sunsets!This roomy home sleeps 10: 4 bedrooms, 3 full bathrooms, one with bathtub, the other two with showers plus an outdoor pool shower. ...

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Property Type

Sarasota Cottage

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Sarasota Vacation Rentals