Vacation Rentals & House Rentals in Port Charlotte

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Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Air conditioning Staffed property Walking trips Secure parking Pets allowed

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Price per night from

$149

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Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

4 of 5 match: Pets allowed, Walking trips, Air conditioning, Staffed property, Secure parking

4 of 5 filters match

Price per night from

$860

Responds fast! avg. 11 minutes

4 of 5 match: Pets allowed, Walking trips, Air conditioning, Staffed property, Secure parking

4 of 5 filters match

Price per night from

$132

4 of 5 match: Pets allowed, Walking trips, Air conditioning, Staffed property, Secure parking

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Price per night from

$285

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: Pets allowed, Walking trips, Air conditioning, Staffed property, Secure parking

4 of 5 filters match

Price per night from

$267

4 of 5 match: Staffed property, Walking trips, Air conditioning, Secure parking, Pets allowed

4 of 5 filters match

Price per night from

$138

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Walking trips, Air conditioning, Staffed property, Secure parking, Pets allowed

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Price per night from

$240

4 of 5 match: Staffed property, Walking trips, Air conditioning, Secure parking, Pets allowed

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Price per night from

$107

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: Staffed property, Walking trips, Air conditioning, Secure parking, Pets allowed

4 of 5 filters match

Price per night from

$193

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

4 of 5 match: Staffed property, Walking trips, Air conditioning, Secure parking, Pets allowed

4 of 5 filters match

Price per night from

$287

Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

4 of 5 match: Walking trips, Air conditioning, Staffed property, Secure parking, Pets allowed

4 of 5 filters match

Price per night from

$158

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.

4 of 5 match: Walking trips, Air conditioning, Staffed property, Secure parking, Pets allowed

4 of 5 filters match

Price per night from

$115

Cape Golf Villa

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

4 of 5 match: Walking trips, Air conditioning, Staffed property, Secure parking, Pets allowed

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Price per night from

$339

Ft. Myers,Lake View Condo, 2BR & 2BA, Best Beaches

Fort Myers condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

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Price per night from

$81

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

3 of 5 match: Walking trips, Pets allowed, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$96

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$161

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$344

Responds fast! avg. 54 minutes

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$268

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 5 match: Walking trips, Pets allowed, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$345

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Walking trips, Pets allowed, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$424

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

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Price per night from

$301

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.

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$510

Modern, child-friendly villa with heated pool, right on the water with jetty

Cape Coral house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$252

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$344

Relax Relax Relax! Close to the RSW airport!!

Fort Myers house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$165

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

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$431

Peaceful escape at Pelican Sound Club

Estero apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$230

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$459

Perfect View: 2-bedroom Unit at Prestigious Vasari

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 5 match: Walking trips, Pets allowed, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$268

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Walking trips, Pets allowed, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$338

Glamorous 3-Bedroom Villa w Pool Sarasota Area

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 59 minutes

3 of 5 match: Walking trips, Pets allowed, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$573

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Walking trips, Pets allowed, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$410

Captiva Villa on Redfish Pass, ocean views from all rooms, beautiful beach

Captiva Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Walking trips, Pets allowed, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$493

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 5 match: Secure parking, Pets allowed, Walking trips, Air conditioning, Staffed property

3 of 5 filters match

Price per night from

$431

“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 5 match: Secure parking, Pets allowed, Walking trips, Air conditioning, Staffed property

3 of 5 filters match

Price per night from

$144

3 of 5 match: Secure parking, Pets allowed, Walking trips, Air conditioning, Staffed property

3 of 5 filters match

Price per night from

$144

The Cannon- A two bedroom adorable cottage minutes walking to beach

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$402

3 of 5 match: Staffed property, Pets allowed, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$509

Viewing 38 of 2,443
rentals in Port Charlotte

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