Vacation Rentals & House Rentals in Port Charlotte

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873 house rentals

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

Match: Private pool Water sports Car not required

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Price per night from

$500

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

Match: Private pool Water sports Car not required

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Price per night from

$121

Match: Private pool Water sports Car not required

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Price per night from

$457

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 40 minutes

Match: Private pool Water sports Car not required

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Price per night from

$744

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Match: Private pool Water sports Car not required

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Price per night from

$1,144

Private Pool Home, SPECTACULAR Sunsets And Only Steps from the Beaches

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private pool Water sports Car not required

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Price per night from

$1,144

Endless Summer - North Captiva Island 3 Bedroom 2.5 Bath, Sleeps 10 - Boat slip

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool Water sports Car not required

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Price per night from

$571

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 40 minutes

Match: Private pool Water sports Car not required

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Price per night from

$1,202

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Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

2 of 3 match: Private pool, Water sports, Car not required

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Price per night from

$429

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private pool, Water sports, Car not required

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Price per night from

$489

Second Star

North Captiva Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

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Price per night from

$658

2 of 3 match: Private pool, Water sports, Car not required

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Price per night from

$332

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

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Price per night from

$229

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

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Price per night from

$320

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

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Price per night from

$274

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

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Price per night from

$286

Beachside of the Village; By Beachside Management

Siesta Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$377

Siesta Beach House; by Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$320

Sun and Sea: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$286

Beach House Residence - Penthouse; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$434

Sea Shell; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$320

Just Beachy: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$377

Beach House Residence - 301; by Beachside Management

Siesta Key apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$629

Palm Bay Club - 303: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$343

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$411

Casa Mar - Unit 3; by Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$263

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$950

Fanta-Sea 47; By Beachside Management

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$457

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$482

Stella Maris-Beachfront, Ultimate Privacy, Spectacular Shelling, Sunset Views!

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$972

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$343

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$172

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$681

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$401

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$560

Ten35 Seaside - Direct Gulf View: Residence 307

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$858

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$377

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Private pool, Water sports, Car not required

2 of 3 filters match

Price per night from

$778

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rentals in Port Charlotte

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