Vacation Rentals & House Rentals in Port Charlotte

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River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Climbing frame Shared outdoor pool (heated) Private outdoor pool (heated) Swing set or jungle gym Swimming pool

All filters match

Price per night from

$229

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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: Private outdoor pool (heated), Climbing frame, Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

4 of 5 filters match

Price per night from

$266

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

4 of 5 match: Private outdoor pool (heated), Climbing frame, Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

4 of 5 filters match

Price per night from

$117

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

4 of 5 match: Climbing frame, Shared outdoor pool (heated), Private outdoor pool (heated), Swing set or jungle gym, Swimming pool

4 of 5 filters match

Price per night from

$1,145

January~April 2024

Estero apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$192

River Hall Fully Furnished

Fort Myers condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$103

Lovely Waterfront Home

Iona house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 26 minutes

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$224

“Lovely Home” The house looked just as the pictures showed. It was beautiful. We enjoyed the pool and hot tub. It was a nice vacation spot.

3 of 5 match: Climbing frame, Shared outdoor pool (heated), Private outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$223

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 5 match: Climbing frame, Swing set or jungle gym, Shared outdoor pool (heated), Private outdoor pool (heated), Swimming pool

3 of 5 filters match

Price per night from

$286

Fort Myers, Lake View, 2Br $ 2BA, Best Beaches

Iona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$81

Responds fast! avg. 54 minutes

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$267

Peaceful escape at Pelican Sound Club

Estero apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$229

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$161

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$622

Snowbird's delight!

Naples villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$344

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$192

2 Bedroom, 2 Bathroom condo / Heated pool / 7 minute walk to beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$178

Responds fast! avg. 11 minutes

3 of 5 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool

3 of 5 filters match

Price per night from

$132

Bonita Isles spectacular Hidden Gem in the heart of Bonita Springs/Naples Fl.

Bonita Springs villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$115

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$573

Come join us for your Winter Migration!!!!!!!!!!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$103

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$430

Friends and Family close to beaches and more

Fort Myers house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$126

Beachfront Condo With Weekly Rentals

Fort Myers Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Estero Sands was PERFECT!!” Estero Sands was a great place for our family! We've stayed in Ft. Myers many times and this stay was one of the best. The owners that were on site were very nice. The grounds were very well kept. Literally steps to the beach!!! Loved it!!

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$327

Guava Getaway - Relax, Renew, and Rejuvenate

Lakewood Ranch condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$171

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$360

2 bedroom Florida condo unit 13 at family friendly resort

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$425

Coastal Retreat

Saint James City condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$95

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.

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 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

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$434

1 bedroom single story condo near pool

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$295

2 bedroom poolside condo steps from ocean beach and dock on bay

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$425

THE CONDO HAS BEEN SEVERELY DAMAGED BY HURRICANE IAN AND IS TEMPORARILY CLOSED.

Sanibel Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$344

THE CONDO HAS BEEN SEVERELY DAMAGED BY HURRICANE IAN AND IS TEMPORARILY CLOSED

Sanibel Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$344

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$338

Burnt Store Marina Main Floor 2 Bedroom 2 Bath Condo

Punta Gorda condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$144

Bright Clean Happy Vacation Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$115

Island Attitude 2/2 beach condo

Manasota Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 5 match: Climbing frame, Private outdoor pool (heated), Swing set or jungle gym, Shared outdoor pool (heated), Swimming pool

2 of 5 filters match

Price per night from

$315

Viewing 38 of 1,862
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