Vacation Rentals & House Rentals in Port Charlotte

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2,389 house rentals

Responds fast! avg. 11 minutes

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Price per night from

$132

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Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Air conditioning, Walking trips, Table tennis, Staffed property

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Price per night from

$114

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 4 match: Staffed property, Walking trips, Air conditioning, Table tennis

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Price per night from

$155

Tropical "Key West" style waterfront paradise with views/pool/spa & boat dock!

North Naples house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Walking trips, Air conditioning, Table tennis

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Price per night from

$315

Lattitude Adjustment- Private Beachfront Home with Fishing Dock, Sunrises

North Captiva Island house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 4 match: Staffed property, Walking trips, Air conditioning, Table tennis

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Price per night from

$916

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$144

Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$858

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$144

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$430

Responds fast! avg. 54 minutes

3 of 4 match: Staffed property, Walking trips, Air conditioning, Table tennis

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Price per night from

$267

LUXURY UPDATED “BEACHFRONT”, Riviera Club Fort Myers Beach, SUNSET VIEWS!!!!!!!!

Fort Myers Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Staffed property, Walking trips, Air conditioning, Table tennis

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Price per night from

$229

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

3 of 4 match: Staffed property, Walking trips, Air conditioning, Table tennis

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Price per night from

$573

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Walking trips, Air conditioning, Table tennis

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Price per night from

$1,260

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$271

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$284

SURF AND TURF ACTIVITY FILLED GOLF RESORT COMMUNITY

Venice villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 31 minutes

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$86

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

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$266

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

3 of 4 match: Table tennis, Walking trips, Air conditioning, Staffed property

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Price per night from

$149

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

3 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

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Price per night from

$453

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

3 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

3 of 4 filters match

Price per night from

$117

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

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Price per night from

$622

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

3 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

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Price per night from

$109

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

3 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

3 of 4 filters match

Price per night from

$115

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

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Price per night from

$745

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

3 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

3 of 4 filters match

Price per night from

$114

Beach to Bay Tropical Oasis! 2Bed/2Bath Longboat Key Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

3 of 4 filters match

Price per night from

$153

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

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Price per night from

$229

Seven Lakes 55 and over Golf and Tennis Resort

Fort Myers condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Air conditioning, Staffed property, Walking trips, Table tennis

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Price per night from

$79

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

2 of 4 filters match

Price per night from

$436

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

2 of 4 filters match

Price per night from

$903

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

2 of 4 filters match

Price per night from

$178

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

2 of 4 match: Walking trips, Air conditioning, Table tennis, Staffed property

2 of 4 filters match

Price per night from

$2,289

North Captiva Private Pool Home Shell Cottage

North Captiva Island house

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

2 of 4 match: Table tennis, Staffed property, Walking trips, Air conditioning

2 of 4 filters match

Price per night from

$458

Beautiful 3 bedroom home in Southwest Florida

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Relaxing Stay” Well kept property in a great neighborhood within 15 min from the beach and great shopping. The pictures and description accurately reflect what you see when you get there. Owners, Lorrie and Frank, were a pleasure to deal with from beginning to end. Had a wonderful time and looking forward to returning soon. Would highly recommend this property!

2 of 4 match: Table tennis, Staffed property, Walking trips, Air conditioning

2 of 4 filters match

Price per night from

$172

New York Avenue Rancher

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Walking trips, Staffed property, Air conditioning, Table tennis

2 of 4 filters match

Price per night from

$445

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Table tennis, Staffed property, Walking trips, Air conditioning

2 of 4 filters match

Price per night from

$250

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Table tennis, Staffed property, Walking trips, Air conditioning

2 of 4 filters match

Price per night from

$164

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Table tennis, Staffed property, Walking trips, Air conditioning

2 of 4 filters match

Price per night from

$232

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