Captiva Island Rentals with Pools

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815 house rentals in Captiva Island with pools

Relaxing Near Beach Captiva Island Pool Home

Captiva Island house

3 bedrooms / 2 bathrooms / sleeps 6

“Absolutely terrific” Everything about our vacation was wonderful. The cleanliness of the house and it's location couldn't have been better. We're planning to go again this year.

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Price per night from

$586

Captiva Mermaid House - Beach Side of Village Center

Captiva Island house

2 bedrooms / 2 bathrooms / sleeps 6

“Relaxing and Enjoyable stay in Captiva” My husband and I loved our stay at the Mermaid House. The house is extremely clean and very well stocked with everything you could possibly need during your stay. The private pool was clean and very refreshing after a day on the beach. Larry Hahn was very responsive to all my questions and emails and even called the night we arrived to check to make sure everything was ok and if we needed anything. I highly recommend staying here while on Captiva. Looking forward to revisiting the Mermaid House and Captiva again soon!

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$490

Sea Dreams: Luxury Ocean and Beach Front Townhome

Captiva Island house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$479

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

$1,430

Sun & Moon Pool House - Beach Side of the Captiva Village Center

Captiva Island house

3 bedrooms / 3 bathrooms / sleeps 8

“25th anniversary. Loved every minute of our stay.” Just got back from a week at the Sun and Moon. There is nothing missing with this rental property. Larry so very helpful with a florist for my anniversary. You will not be disappointed in this property, nice and close to many different eateries, liquor stores, there are bikes provided and a big beach cart full of everything, really everything. Sunsets are not to be missed. Can't wait to go back.

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$555

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

$491

Anthony Beach Cottages Sunset Captiva 49

Captiva Island house

2 bedrooms / 3 bathrooms / sleeps 5

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Price per night from

$286

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

Sea Otter House- Luxury Estate on Captiva Drive

Captiva Island villa

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$686

Luxurious Waterfront Condo at South Seas Resort- Bikes Included

Captiva Island house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$400

Harbor Front Condo at South Seas Resort- Includes Bikes

Captiva Island apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$342

Ultra Luxe Beach Villa at South Seas Resort

Captiva Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$571

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

$2,997

Sunsplashed -- Your own private tropical island resort!

Captiva Island villa

5 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$1,377

Great rentals within 20 miles that match your search

2BR/2BA CONDO North Fort Myers Quiet near Marina

North Fort Myers apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$77

Paradise in Fort Myers

Fort Myers villa

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$140

Lakeview

Fort Myers villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$159

Waterfront Heated Pool Propert

Cape Coral villa

3 bedrooms / 2 bathrooms / sleeps 8

“Wonderful place! Relaxing!” Owners were nice people to work with, answered questions in a timely manner. The place was very comfortable, quiet, and enjoyable. Would definitely return!

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$182

Halcyon Days, great location, 2 en suite masters, near amenities, well equipped.

Fort Myers house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 2 minutes

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Price per night from

$211

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!!

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$246

Siesta Isle Paradise

Fort Myers Beach house

4 bedrooms / 2 bathrooms / sleeps 8

“Awesome” This is a full sized home with ample space for a family of 8...or more. The lower level area to the pool was perfect for our teen aged son. Gave him privacy from the rest of the clan and made for a very peaceful week together! Pool is perfect and good size and fishing from dock was excellent...snook were biting! We would see manatees and dolphins every single day! My wife and I would be interested in a month's stay after our son graduates next year. About 1 mile from beach with trolleys stopping out on main road so made for easy trips to the beach for the day. This was truly a very pleasant experience in a very nice home and nice area with every amenity you would find at a top notch hotel for much more money and way less room. Perfect for 2 families or 2 couples without being on top of each other!

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Price per night from

$401

Luxury Condo on Beach Sleeps 6 Sanibel Island, FL

Sanibel Island apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$310

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

$229

Pointe Santo D4 Ground Floor Condo

Sanibel Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful” We booked this condo for five nights in August. The condo is in excellent condition and the location was perfect. The owners were fantastic to work with. We would rent this condo again in the near future. We love Sanibel Island.

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Price per night from

$303

Beautiful beachy condo on quiet end of Sanibel Island, Florida

Sanibel Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$135

***Sanibel Island - Best Kept Secret!! Free Kayaking and Private Beach Access

Sanibel Island condo

2 bedrooms / 2 bathrooms / sleeps 6

“Quiet, private, homey feel” The condo was very clean and spacious. The owner provided chairs, umbrellas, beach cart, beach towels, cooler, everything you needed to have a great stay. We enjoyed playing the provided games in the room at night. We were pleasantly surprised by how quiet the area was. The pool is large and easy to find a place in the sun or shade depending on your preference. The beach is a longer walk than we had anticipated but it is mostly shaded, but the quietness and private beach access made up for the distance. If you love Sanibel you won't be disappointed in this unit. We commented numerous times that the area seemed more relaxing than other beach vacations we have taken.

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Price per night from

$167

BACK TO THE BEACH SPECIAL! $199/Night - Best Value Guaranteed!

Fort Myers Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

“This area was easy to get around but the Trolley was a fun way to visit FMB areas . . .” Our 2 bedroom, 2 bath 6th floor unit had a view of the intercoastal waterway (from 1 bedroom) as well as the beach view from the master bedroom & our screened corner balcony. It was very clean and well stocked with dishes and cookware; the appliances worked well and were clean. They loved their bedroom with the extra long full size beds. The building is right on the beach for easy access with 2 grandchildren. Easy walk to the Bowditch Point Park and Times Square. We really enjoyed the Ostego Bay Foundation Marine Science Center. Highly recommended.

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Price per night from

$915

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

Cape Coral villa

3 bedrooms / 3 bathrooms / sleeps 6

“Savannah house” Had a great time!!! Place was awesome as advertised!! Peter the property manager was great as well! We hated to leave!

Responds fast! avg. 3 hours 35 minutes

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Price per night from

$308

Gulf Front Complex, Renovated 2 Bd Condo Free Wifi

Sanibel Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Paradise!” This was our sixth time on the Island. This time we stayed at Julie Klemen's beautiful condo. We spent most of the week outside on the beach. Dolphins swimming by, lots of sanddollars and only a few people on the beach. We really loved this relaxing time. In the condo you will find everything you need. Beachtowels, washer, dryer, beachtoys and so on. We had breakfast outside every morning with a beautiful view over the beach and pool. We had a very nice contact with Julie by email. She informed us about what you can do on the Island. We made beautiful memories!

Responds fast! avg. 48 minutes

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Price per night from

$247

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

$234

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

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

$246

Villa Miami, southern exposure, with boat (optiona

Cape Coral villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$247

GIGA-HOMES "Casa Tina", Gulf ACCESS

Cape Coral house

3 bedrooms / 2 bathrooms / sleeps 6

“Sunshine, Perfect location and Clean” Let me start off by saying the only negative about this house was the carpet in the bedrooms. I would so stay there again, of course if they change the flooring in bedrooms. This was a wonderful rental for our family in between Christmas and New Years. Very Clean when we arrived, heated pool was clean and perfect. Great neighborhood, we actually had an issue with the air and between property manager and neighbor it was quickly resolved! We walked in the neighborhood every morning, met a few. I wish I would of taken pictures of inside of house, the couches are now new leather couches, we didnt use the dishes they had because I was on vacation...but they looked brand new to me! The property manager Gunther was great, he came couple hours after we arrived and went through house with us, we actually sat and chit chatted with him for awhile about Florida. It was only about 1/2 hour from Fort Meyers. Im not one to write reviews but felt for a house rental I needed to!!

Match: Swimming pool

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Price per night from

$201

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 28 minutes

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Price per night from

$286

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

Sanibel Island apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Great Time On Sanibel” We stayed at the condo mentioned above and found it to be great. Very clean and very comfortable. We plan on staying in this condo the next time we vacation on Sanibel

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Price per night from

$196

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