Captiva Island Rentals with Pools

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657 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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Price per night from

$1,432

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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Price per night from

$492

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

$642

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

$3,000

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

Villa American Eagle/Cape Coral

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$224

Casa Indulgence in Matlacha

Matlacha house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$802

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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

$258

Island Villa + 33' Infinity Pool, Dolphin Visits

Fort Myers Beach villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$307

Villa Weiss in Cape Coral

Cape Coral house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$284

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

$464

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

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$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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Price per night from

$241

Gulfview paradise

Fort Myers Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$401

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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Price per night from

$245

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

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Price per night from

$172

Villa Leonardo - Heated Pool, Canal Access w/Boat Lift, 4 bdrms, Sleeps 10+

Cape Coral house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

“Absolutely perfect!!” This house has everything you could ever need or want away from home. Our group consisted of 6 adults and 6 children (including 2 toddlers), this house was perfect. Everyone had space to sleep comfortably, and we all had enough space to enjoy our company without driving each other crazy lol The house is set up with everything you need, we were amazed to find toiletries in the bathrooms and the garage so well stocked up. First time we ever find this at a rental property. The kids loved the beach and pool toys. The beach chairs and umbrellas were perfect for our visits to Fort Myers Beach and Sanibel. We had enough beach towels for everyone too which is a big plus! The kitchen had everything we needed, even Dunkin Donuts coffee! We had a great time making easy meals to accommodate everyone's taste. The grill was perfect for making a great meal and enjoying it outside. If you need to take a break from the everyday hassle, you do not need to look any further! This house is perfect, has everything you need, in perfect condition, with a great surround system. We hope to visit again next year! Thank you for allowing us to enjoy your property!

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Price per night from

$206

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

$308

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

2 Bedroom Beachfront Condo at Sanibel Harbour

Fort Myers apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$195

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

Cape Coral villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$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

$258

One minute walk to gulf beaches, Big, 3 BR, 55 inc

Sanibel Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$308

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

$377

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

$166

Seashells and Sunsets

Sanibel Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Rest and Relaxing---What a nice week!!” We thoroughly enjoyed our stay. The bedrooms were large compared to may places I have stayed.. We were not affected by the storm on the east coast of FL. Large living room, very well furnished kitchen. Great washer/dryer. Sharon-MI.

Match: Swimming pool

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Price per night from

$360

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

Match: Swimming pool

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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.

Match: Swimming pool

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Price per night from

$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

$258

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

$196

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rentals in Captiva Island

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