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: Cot available Air conditioning Staffed property Walking trips Secure parking

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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: Cot available, Walking trips, Air conditioning, Staffed property, Secure parking

4 of 5 filters match

Price per night from

$857

Responds fast! avg. 12 minutes

4 of 5 match: Cot available, Walking trips, Air conditioning, Staffed property, Secure parking

4 of 5 filters match

Price per night from

$143

4 of 5 match: Cot available, Walking trips, Air conditioning, Staffed property, Secure parking

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Price per night from

$284

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: Cot available, Walking trips, Air conditioning, Staffed property, Secure parking

4 of 5 filters match

Price per night from

$266

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

4 of 5 match: Walking trips, Cot available, Air conditioning, Staffed property, Secure parking

4 of 5 filters match

Price per night from

$189

Bonita Beach Villa, private heatable pool, close to beaches,

Bonita Springs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Walking trips, Cot available, Air conditioning, Staffed property, Secure parking

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Price per night from

$286

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Walking trips, Cot available, Air conditioning, Staffed property, Secure parking

4 of 5 filters match

Price per night from

$178

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

Fort Myers condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

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Price per night from

$80

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, Cot available, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$95

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$160

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

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Price per night from

$342

Responds fast! avg. 54 minutes

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$267

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 5 match: Walking trips, Cot available, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$343

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Walking trips, Cot available, Air conditioning, Staffed property, Secure parking

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Price per night from

$423

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$138

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

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.

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$508

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$343

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: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$252

Relax Relax Relax! Close to the RSW airport!!

Fort Myers house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$164

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: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$429

Peaceful escape at Pelican Sound Club

Estero apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$229

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$458

Vacation Rental Boutique Suite Windmills

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 5 match: Walking trips, Secure parking, Cot available, Air conditioning, Staffed property

3 of 5 filters match

Price per night from

$223

Perfect View: 2-bedroom Unit at Prestigious Vasari

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 5 match: Walking trips, Cot available, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$267

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, Cot available, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$337

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, Cot available, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$572

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Walking trips, Cot available, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$409

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, Cot available, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$491

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

3 of 5 match: Walking trips, Cot available, Air conditioning, Staffed property, Secure parking

3 of 5 filters match

Price per night from

$240

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 5 match: Cot available, Secure parking, Walking trips, Air conditioning, Staffed property

3 of 5 filters match

Price per night from

$429

3 of 5 match: Cot available, Secure parking, Walking trips, Air conditioning, Staffed property

3 of 5 filters match

Price per night from

$143

“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: Cot available, Secure parking, Walking trips, Air conditioning, Staffed property

3 of 5 filters match

Price per night from

$143

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

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$401

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

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

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$193

3 of 5 match: Cot available, Staffed property, Walking trips, Air conditioning, Secure parking

3 of 5 filters match

Price per night from

$507

Viewing 38 of 2,367
rentals in Port Charlotte

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