Vacation Rentals & House Rentals in Port Charlotte

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10,001 house rentals

Weekly 2 bedroom Apartment for 8 guest all amenities included

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 17 minutes

Match: Boat available Swimming pool Smoking allowed Car not required

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Price per night from

$121

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3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

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Price per night from

$103

Cottage By The Water With Boat Dock

Tarpon Springs cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

“Awesome-perfect in every way” We cannot say enough possitive things about this home and the hosts. We have come to Tarpon for 30 years but this is the first time we ve used flipkey and we will only use flipkey from now on. From the welcoming hug to the perfect ammenities throughout, you could not beat this offering. Location is beautiful and perfect to access anything. The hosts were so nice and they had paid attention to so many details, we were overwhelmed. They had lots of suggestions and a great notebook filled with menus and things to do. Plus hints on specials, fishing and the area. As we ended our trip they even greeted us with a weather report--there was a storm headed our way. Thank you both for making sure this was the best time we ve ever had in this, our favorite, Florida location.

Responds fast! avg. 36 minutes

3 of 4 match: Swimming pool, Boat available, Smoking allowed, Car not required

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Price per night from

$138

Key West Flair

Sanibel condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

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Price per night from

$311

Beautiful Barrier Island Beach House with Pool, Spa and Dock - Walk 2 Beach!

Don Pedro Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

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Price per night from

$596

Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

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Price per night from

$858

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

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Price per night from

$2,119

Beautiful Large Studio Condo on the Lake

Orlando apartment

  • 1 bathroom
  • sleeps 4

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

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Price per night from

$228

Private Pool Home, SPECTACULAR Sunsets And Only Steps from the Beaches

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

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Price per night from

$1,145

Endless Summer - North Captiva Island 3 Bedroom 2.5 Bath, Sleeps 10 - Boat slip

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

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Price per night from

$572

Bahia Beach Resort Little Harbor-Tampa, FL

Tampa studio

  • Studio
  • 1 bathroom
  • sleeps 4

“Perfect Vacation Relaxation Spot” The view from the room and balcony was gorgeous. Sitting on the balcony each morning sipping my coffee was heavenly. All of the amenities were close to the room and just short walks away. The property itself was well maintained and quiet while still being family friendly. The room was comfortable and a great home base at the end of our daily jaunts. Tampa, St. Petersburg, and Clearwater were very easy drives from the Inn. I can't wait to visit again.

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

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Price per night from

$138

NSS Pattam, custom 84 foot traditional motor yacht downtown.

St. Petersburg yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 42 minutes

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

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Price per night from

$1,374

LUXURY Town Center Villa Disney Studio APT

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

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Price per night from

$198

Walk to Indian Rocks Beach Exclusive Use of Hot Tub, Pool, BBQ with Privacy*#!!!

Indian Rocks Beach house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

3 of 4 filters match

Price per night from

$114

LUXURY Lakes Villa Disney Studio APT

Orlando villa

  • 1 bathroom
  • sleeps 5

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

3 of 4 filters match

Price per night from

$192

Deluxe Queen Suite in Gorgeous Pop Art Gallery Pool Home Close to Everything!

St. Petersburg private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

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Price per night from

$144

Cozy & Conveniently located Pool Home w/ Free WiFi

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

3 of 4 filters match

Price per night from

$205

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$744

River Island - North - East - West Villages at Orange Lake

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$246

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$1,145

Lattitude Adjustment- Private Beachfront Home with Fishing Dock, Sunrises

North Captiva Island house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$916

Stella Maris-Beachfront, Ultimate Privacy, Spectacular Shelling, Sunset Views!

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$974

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

3 of 4 filters match

Price per night from

$158

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

3 of 4 filters match

Price per night from

$800

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

3 of 4 match: Boat available, Swimming pool, Smoking allowed, Car not required

3 of 4 filters match

Price per night from

$149

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$344

Beautiful 2 Bedroom Condo on the Lake

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$343

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$1,946

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$487

Responds fast! avg. 30 minutes

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$114

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$272

EIKO BEACHFRONT HOME 4BR/3BA**HEATED POOL&SPA*PETS OK

Treasure Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

“Water, water everywhere” So very, very close to the beach. Very helpful agent. Had 11 people with plenty of room .awesome time.

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$773

PRIVATE BEACH OPEN** Beachfront bungalow 4BR *Htd POOL*Pet

Indian Shores house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“A wonderful place to be!” Our rental was right on the pool/beach. It was perfect! Gorgeous pool and the beach - beautiful, private - everything you could want. The cottages were spacious, clean and kitschy. They had everything you needed. You could tell good people stayed there as everything was well kept and stocked. The owner, Liz, was lovely and even though we had no pets, every pup there was well behaved and everyone was respectful of the rules. The people staying at the other cottages were wonderful and had stayed there before. Obviously Liz knows what she’s doing . My parents also stayed with us and both of them loved the place. The beds were very comfortable which doesn’t always happen in rentals. Hoping to see you next year! Cheers!

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$487

BEACHFRONT BUNGALOW Marlin Hideaway *Htd Pool*Pets

Indian Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Amazing!” Second time back and even better. Everything we needed to escape the craziness of COVID-19. Got to meet some new friends in the other bungalows and enjoy the beautiful beech! Can’t wait to return.

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$423

BEACHSIDE BUNGALOW Lobster Shack *Htd Pool*Pets OK

Indian Shores cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“What a great getaway location to relax and view the secluded private beach and gorgeous ocean view!!!” We stayed in the Lobster Shack which is a cozy clean bungalow which offered a salt water pool with an awesome view of the Gulf waters. Liz is great making sure our needs were met while addressing unexpected refrigerator problems. She is quick to reply contacting a repairman to resolve the issue. Canines are welcome. I miss the relaxation and calmness of the setting yet on Gulf Blvd there are activities to meet everyone's interests. Thank you Liz and love your puppies.❤

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$189

BEACHSIDE BUNGALOW Dolphin 2BR*HTD POOL*PETS OK

Indian Shores cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Thanksgiving Getaway” Beautiful location and our pet was able to come along. We enjoyed the beach, fire pit and weather. The one negative is that our unit was very close to a busy road.

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$228

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 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$509

Luxury Beach Front Villa with Pool, Captiva Island

Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Sunset Dreams - Tropical Paradise” What a wonderful place! We just returned and we miss it very much already. As my wife puts it, "it was like being in another world!" She's become an overnight ornithologist and marine biologist. The owners went well above the standard of what a normal property rental would be. From furnishings, to decor, to kitchen utensils, and appliances; they blow every rental property we've ever seen right out of the water. The home is immaculate. And the island itself has endless things to do. We've already booked for next year!

3 of 4 match: Smoking allowed, Boat available, Swimming pool, Car not required

3 of 4 filters match

Price per night from

$642

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