Vacation Rentals & House Rentals in Port Charlotte

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Bocilla Island Club 2 Pools, boat dock, private 400 ft fishing pier

Bokeelia condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Air conditioning Children's pool Satellite TV Walking trips Secure parking

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Price per night from

$218

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Townhouse in Resort Community of Gran Paradiso

Venice apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Walking trips, Air conditioning, Children's pool, Satellite TV, Secure parking

4 of 5 filters match

Price per night from

$237

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Walking trips, Air conditioning, Children's pool, Satellite TV, Secure parking

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Price per night from

$224

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$342

Responds fast! avg. 54 minutes

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$267

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$300

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$509

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

4 of 5 match: Walking trips, Air conditioning, Children's pool, Satellite TV, Secure parking

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Price per night from

$205

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$430

Close to Siesta key with hot tub, fire pit and butterfly garden

Gulf Gate Estates guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$192

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$284

★ Secluded Holiday Retreat/ Island Paradise & Waterfront Condo ★

Little Gasparilla Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

4 of 5 match: Walking trips, Air conditioning, Children's pool, Satellite TV, Secure parking

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Price per night from

$319

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$506

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

4 of 5 match: Children's pool, Walking trips, Air conditioning, Satellite TV, Secure parking

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Price per night from

$266

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

4 of 5 match: Walking trips, Air conditioning, Children's pool, Satellite TV, Secure parking

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Price per night from

$113

Lake Kennedy charming Villa

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Walking trips, Air conditioning, Children's pool, Satellite TV, Secure parking

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Price per night from

$298

Cape Coral Vacation Villa

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Great Week” The house was spotless. Well equiped. Felt right at home. Would deffinately stay at this home again. Owner was great.

4 of 5 match: Walking trips, Air conditioning, Children's pool, Satellite TV, Secure parking

4 of 5 filters match

Price per night from

$287

Venice Immaculate RemodeledHome-2 Bdr/2 Bath-Pool-WIFl&CABLE-2 Miles to Beach

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Walking trips, Air conditioning, Children's pool, Satellite TV, Secure parking

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Price per night from

$172

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Children's pool, Satellite TV, Walking trips, Air conditioning, Secure parking

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Price per night from

$161

Pet friendly newly renovated 3 bedroom home

Lehigh Acres house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

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Price per night from

$82

3 of 5 match: Children's pool, Satellite TV, Walking trips, Air conditioning, Secure parking

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Price per night from

$137

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

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Price per night from

$573

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

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Price per night from

$229

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

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Price per night from

$229

Lovely 2 Bedroom Home near the Beach

Cape Coral house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 36 minutes

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$166

Beachplace Building 7 Great View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$180

Modern Mansion with Private Arcade: Pool, Views & Space for 15 Guests!

Port Charlotte house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$655

SIestaKeyBNB

Gulf Gate Estates house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$241

Siesta Key/Derby Bay

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect!” Our family really enjoyed staying here! The villa was very well maintained and cleaned. It was stocked with everything you would need. The owner was very responsive to any concerns. We had a super nice neighbor and my boys loved fishing off the dock. I would recommend renting a golf cart to go to the beach if you have children (with toys etc) or elderly people with walking concerns. It is quite a walk to get to the beach (because you also have to walk down to the cross walk then across the street). The beach in front of the Aloha Kai property is very wide (great because it was never crowded like in front of other resorts) but it was an even farther walk to the water. We have always stayed beach front but needed more rooms than were available in my booking time frame this year. This property has changed the way I will book on siesta in the future. My boys LOVED fishing everyday off the dock. They caught lots of cool fish right off the back. The street that this villa is on was very quiet for our stay. Everyone was very kind & the property is very beautiful! We hope to come back very soon! It was a wonderful experience.

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$287

“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$434

North Captiva Private Pool Home Shell Cottage

North Captiva Island house

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

3 of 5 match: Children's pool, Secure parking, Walking trips, Air conditioning, Satellite TV

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Price per night from

$458

“gracious and spacious” Lovely home and great location to walk throughout Siesta Key Village and the beautiful sands of the beach!! We were able to have everyone together for a great vacation.

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$148

Just another day in paradise! Sunrise condominiums!

Bee Ridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$115

Tropical House in Bokeelia w/pool, dock access to the Gulf of Mexico

Bokeelia house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$491

Beautiful Waterfront with Heated Pool & Gulf Access

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$316

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$401

Luxury Villa Emerald Coast

Cape Coral villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 5 match: Walking trips, Children's pool, Air conditioning, Satellite TV, Secure parking

3 of 5 filters match

Price per night from

$492

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

3 of 5 match: Children's pool, Secure parking, Walking trips, Air conditioning, Satellite TV

3 of 5 filters match

Price per night from

$155

Viewing 38 of 1,124
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