Captiva Island Rentals with Pools

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658 house rentals in Captiva Island with pools

Captiva Bayfront 4 bedroom/4 bath, boat dock, pool

Captiva Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Most amazing vacation on Captiva Island!” We had a great time on Captiva Island. We have stayed there several times, but this time we chose to stay at this private home on the bay. My husband and I were relaxed and the kids had plenty of room to run and explore. The house was amazing - beautiful views, lots of room, great pool and very private but close to everything we could possibly need.

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$1,434

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

Captiva Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$493

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!

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Price per night from

$644

Captiva Star - Luxury Near Beach Home on Captiva

Captiva Island house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 18

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Price per night from

$2,999

Captiva Waterfront Luxury Home Rental

Captiva Island house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

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Price per night from

$1,718

Sunsplashed -- Your own private tropical island resort!

Captiva Island villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,633

Great rentals within 20 miles that match your search

Casa Indulgence in Matlacha

Matlacha house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$803

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Price per night from

$69

Pool Home with Gulf Access

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$259

Villa Weiss in Cape Coral

Cape Coral house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$283

Private Gated Community

Cape Coral house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$201

Cape Coral Florida Banyan Trace condo

Cape Coral condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$138

Three Bedroom 3 Bath Waterfront Vacation Rental

Cape Coral condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$465

Villa BlueBay * Top Location* SW Pelican* Pool* Waterfront*Gulf Access

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$224

VILLA MAMA - Traumvilla mit Golfzugang, Bootseinstieg im eigenen Garten

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 18 minutes

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Price per night from

$211

Villa Aurelia

Cape Coral house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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$241

Gulfview paradise

Fort Myers Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$402

THE FANCY FISH..Enjoy Pool "Sandy Beach" Boat Lift

Matlacha house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“If you want an awesome getaway without having to leave the property for fun...this is your place!” This home has an awesome dock for fishing, boat lift, swimming pool, sandy beach with beach chairs, kayaks and completely fenced in property in case you want to bring your pet with you. The chef's kitchen is amazing with top of the line appliances for all of your meals that you will want to cook. You can walk to the shops and restaurants that are iconic to this area. A definite return for us!

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$246

Casa Del Rio, Tropical Resort,River View,Pool&Dock

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Relaxation” We stayed at Casa Del Rio for 10 days and from the moment we got there we felt at home. The property manager meet with us and we very helpful and informative. The home has everything you need the pool area is large enough to host several people. However, nothing will ever top getting an opportunity to see dolphins swim right up to the dock. It was an awesome experience and we really enjoyed our stay!!

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Price per night from

$247

Sunsets from the Lanai. Luxury Villa with Heated

Cape Coral villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Outstanding place for a great vacation!” I thoroughly enjoyed my stay. The home was decorated beautifully and very conducive to a relaxing vacation. All the amenities of home. We could either relax by the pool overlooking the canal, or a quick drive to the beach, great restaurants and shopping. The welcome note and bottle of wine was a very classy touch. I will definitely be back. Thank-You!

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Price per night from

$309

Fun in the Sun Beachwalk Isles Fort Myers Florida

Fort Myers villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$158

Sunrise from Lanai, heated pool, hot tub & White Sandy Beach

Cape Coral villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$343

Cape Coral Delight Villa near Cape Harbour

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$263

SANIBEL HARBOR RESORT 2/2 PANORAMIC BAYFRONT CONDO

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$259

Just Seconds From The Beach at Pointe Santo, A3

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$378

High Season:Jan.-April minimum 60 days. Low Season: May-Dec discounted rates

Cape Coral villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice place for a vacation” I stayed here for four days so that I could see some Red Sox games. The place was very clean and neat, with a kitchen that had everything you need to cook. Juan was very helpful and had lots of suggestions. I really enjoyed my stay! There was plenty of room and it was a nice get-away.

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Price per night from

$167

Waterfront Villa Marie w/ Direct Gulf Access / Private / Hot Tub

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Good value” The home was clean and inviting. The pool and hot tub provided hours of fun! It met my family of fives needs. We would stay here again. The deposit was returned in a timely manner.

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Price per night from

$247

Villa Miami, southern exposure, with boat (optiona

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$248

Paradise on Earth - Direct Beach Front Condo with High Speed Internet

Fort Myers Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“fabulous” This condo is beautiful. We watched the dolphins from the balcony. We enjoyed the heated pool. Access to the beach is right there. The condo had everything we needed and more. Beautifully decorated . We would highly recommend it.

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$164

3 BR/2 BA- Quiet South end of Fort Myers Beach

Fort Myers Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Updated condo, great pool, awesome owner” This is a great rental condo. It is in a great location on a marina, just across the street from the beach (just an easy 5 minute walk). A real bonus is the location near the Santini Plaza. The Plaza has great restaurants, a liquor store, a hardware store and other shopping. There is a CVS next to the Plaza. The pool is beautiful and the largest on the island. It was great to have the extra space of a 3-bedroom, 2-bath unit. Vito is a fantastic owner. He is easy to contact and genuinely cares about his renters.

Responds fast! avg. 3 hours 45 minutes

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Price per night from

$259

Island Paradise. 1st Fl. Water views WiFi, HDTV

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Vacation in Paradise!” Our vacation in Sanibel Island at Maggi's condo was a vacation in Paradise! This was our first time in Sanibel Island and it was a great vacation and I hope to come back and stay at Maggi's condo. What a beautiful island! There was everything we needed in the condo and sitting in the lanai in the morning and at night having our coffee or drinks watching the dolphins was amazing. The information and directions that Maggi gave us were great and she was always available if we had any questions. Our preference was the lighthouse beach. We did go visit Bowman Beach and that was also very nice. Captiva Island is beautiful but you must get there early or there is no parking. I would recommend the thriller boat ride it was great and what an amazing dolphin show! There is something to do for everyone beaches, bike rides and nature! There are many restaurants on the island and they were all good and many shops for shopping. It was very hard to leave Sanibel paradise!

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Price per night from

$197

Great 2/2 Sanibel Condo, Nice Pool, Private Beach

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Sunshine, beaches, What's not to love?” My husband and I stayed at this pleasant 2 bedroom condo with 2 grown children and one son-in-law. The two bedrooms and two baths worked fine for our group. Our married daughter and hubby had to share a bedroom with her brother. The furnishings in the condo were comfortable and clean without being too new to cause worry about a little sand. There were all sorts of beach toys and towels available. The kitchen had a full range of dishes and I cooked fresh fish from the local grocery store several nights. It was convenient to walk to the lovely uncrowded beach with no high-rises in sight. we kayaked with the condo's kayaks in the lagoon and saw a large range of birds, including an osprey feeding on a fish. We had gorgeous weather and collected quite a few shells. Would definitely return.

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Price per night from

$158

Casa Bones Del Mar - Family Reunion House. STR # 20-0041

Fort Myers Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

“3 childhood friends back to Florida again after 30 years, along” This beach home was a perfect location for the pleasures of a beautiful beach. It accommodated us quite nicely. The close proximity to the pier, time square,restaurants and grocery stores was nice, however the trolley was a little unreliable at times. It can become quite the busy stip. The kids enjoyed the dolphins that can be seen frequently on the shores of the beach and at the pier. Our son was a frequent fisherman on the beach catching shark, catfish and jacks! Coming from Canada in February was a definite break from our long cold winter. The Florida sunshine made us crave our long awaited Spring.

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Price per night from

$689

NATURES VIEW FAMILY REUNION HOME STR#20-0064

Fort Myers Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Great family fun!” Our extended family live far apart so we rented the house for a week to spend some time together. There were 13 of us staying in the house, 5 ages thirteen and under! We had a great time. The kids loved the pool and all the space in the house. There was enough room that we didn't feel like we were tripping all over one another and each had our own space. The walk to the beach is easy and short so frequent trips were made there. It is also only a little over a mile to the "Plaza" where there are lots of stores, restuarants, etc. The wagon was very helpful for the little ones when we made this trip. The owner is very easy to work with and the house is well stocked with towels, dishes, toilet paper, etc. I would recommend this house to anyone wanting a vacation away from home. We loved it!!

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Price per night from

$918

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!

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Price per night from

$353

House Sunset Palace with heated pool on canal

Cape Coral house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“The perfect for a family vacation !” We found Sunset Palace to be very comfortable for our large family and very well located. Close to everything we needed. The house was very well maintained and clean. The kids loved the heated pool and I loved the spacious lanai.The rental company was efficient and friendly.We wouldn't hesitate to rent again. Thanks Vacationhit.

Responds fast! avg. 3 hours 0 minutes

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Price per night from

$281

Cape Coral Vacation Villa

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Great Week” The house was spotless. Well equiped. Felt right at home. Would deffinately stay at this home again. Owner was great.

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Price per night from

$287

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Price per night from

$253

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