Vacation Rentals & House Rentals in Port Charlotte

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1,936 house rentals

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

Match: Shared outdoor pool (heated) Pool or snooker table Swing set or jungle gym Swimming pool Car not required

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Price per night from

$117

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St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

4 of 5 match: Swing set or jungle gym, Shared outdoor pool (heated), Pool or snooker table, Swimming pool, Car not required

4 of 5 filters match

Price per night from

$258

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

4 of 5 match: Swing set or jungle gym, Shared outdoor pool (heated), Pool or snooker table, Swimming pool, Car not required

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Price per night from

$183

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

4 of 5 match: Pool or snooker table, Shared outdoor pool (heated), Swing set or jungle gym, Swimming pool, Car not required

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Price per night from

$1,147

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

4 of 5 match: Swing set or jungle gym, Shared outdoor pool (heated), Pool or snooker table, Swimming pool, Car not required

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Price per night from

$109

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!!

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

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Price per night from

$327

Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

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Price per night from

$928

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

4 of 5 match: Car not required, Shared outdoor pool (heated), Pool or snooker table, Swing set or jungle gym, Swimming pool

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Price per night from

$230

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: Car not required, Shared outdoor pool (heated), Pool or snooker table, Swing set or jungle gym, Swimming pool

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Price per night from

$266

Responds fast! avg. 54 minutes

4 of 5 match: Car not required, Shared outdoor pool (heated), Pool or snooker table, Swing set or jungle gym, Swimming pool

4 of 5 filters match

Price per night from

$268

Responds fast! avg. 11 minutes

4 of 5 match: Car not required, Shared outdoor pool (heated), Pool or snooker table, Swing set or jungle gym, Swimming pool

4 of 5 filters match

Price per night from

$132

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 5 match: Shared outdoor pool (heated), Swimming pool, Pool or snooker table, Swing set or jungle gym, Car not required

3 of 5 filters match

Price per night from

$114

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$2,064

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

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Price per night from

$550

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$425

Luxurious Condo Directly on Gulf Steps to Sand!

Fort Myers Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$344

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$263

Siesta Beach House; by Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$320

Sea Shell; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$320

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$515

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$412

Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$430

Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

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Price per night from

$859

Anna Maria Island Vacation Rental

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Island Paradise” The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a fully stocked linen closet, right down to beach towels. Laine, Kevin and Howard are so responsive and saw to all of our needs. Location was prime. We walked to get groceries, eat and do other shopping. There were 7 miles of beaches to explore and the quaint villages of anna Maria and Cortez and Bridge Street kept us occupied when we weren't soaking up the sun. The lanai was my favorite place to drink my coffee and check out the action at the pool each morning . We ate the majority of our meals there, under the twinkling lights. It was a wonderful month!

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$167

Jamaica Royal Villas - Villa 42; by Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$240

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

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: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$492

Palm Bay Club - G46: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$286

Fort Myers Beach 1st Floor

Fort Myers Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 11 minutes

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$138

2 Bedroom Penthouse Sanibel Gulf Front Condo

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Perfect” Absolutely perfect experience! The view was amazing, the condo exquisitely decorated, and the weather cooperated throughout the week! I have rented many condos at Pointe Santo, and this one is definitely a 5 star! We will be back! Thank you, Renee, for being so easy to work with and more importantly, for sharing your lovely condo!

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$352

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$315

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$101

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$190

“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: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$144

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$333

GULF COAST DESTINATION

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$201

Bianco Sands - 2 Bedroom - Poolside: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$332

Casa Mar - Unit 22: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 5 match: Swing set or jungle gym, Pool or snooker table, Shared outdoor pool (heated), Swimming pool, Car not required

3 of 5 filters match

Price per night from

$263

Viewing 38 of 1,936
rentals in Port Charlotte

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