15 Best Captiva Island Vacation rentals on Holiday Lettings - Cottages

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1,720 Vacation rentals

(2) Excellent 

36

Vacation home rental

Southwest Gulf Coast / Captiva Island

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This unique luxury 5300 sq.ft. home ( recently remodeled ) is nestled on an acre of tropical charm with a 450 foot sandy driveway.There is deeded beach access directly across the road . Secluded on the pool side of the house is a tiny private beach and a private dock on …see more

from $427 / night

$2,988 - $5,338 / week

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from $427 / night

10

Home rental in Captiva Island

Southwest Gulf Coast / Captiva Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning
"The Old Key West House" and some younger folks call it, "The Tree House", but whatever you call it, you will love being nestled in the natural lush vegetation like a tropical rain forest.The house has many special architectural features like an English antique stain gl …see more

from $195 / night

$1,365 / week

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from $195 / night

79

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Huge 5 bedroom / 6 bathroom estate on bay directly across from Gulf beaches on Captiva's sought after Gold Coast. This family retreat on the Southern end of Captiva provides access to Captiva's world reknown wildlife eco paradise via the Roosevelt Channel to adjacent Bl …see more

from $600 / night

$4,200 / week

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Responds fast!
avg. 3 hours 22 minutes

from $600 / night

(3) Excellent 

26

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Recently updated home located in Sunset Captiva is a nicely maintained 59 home development located in the heart of Captiva offering a heated swimming pool, tennis courts, private boardwalk leading to the Gulf of Mexico and a boat dock (included w/ rental) located on the …see more

from $265 / night

$1,850 - $2,850 / week

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from $265 / night

(4) Excellent 

16

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
You are just 300 steps from the beach in this private and secluded 3bedroom/3bath vacation home. The Captiva Cottage is the only home on this over one acre property nestled among other estate zoned properties in this stretch of Captiva Island, also referred to as the G …see more

from $285 / night

$2,000 / week

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from $285 / night

17

Vacation home with golf nearby in Captiva Island

Southwest Gulf Coast / Captiva Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Welcome to Sunset Captiva 57 – your own little piece of paradise! Sunset Captiva is a small, charming, unique community located in the heart of Captiva Village Center - there is nothing else quite like it on the west coast. Stretching from bay to gulf, it really has it …see more

from $222 / night

$1,550 - $2,750 / week

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from $222 / night

19

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in a small beach-to-bay community on the scenic Captiva Island, this fully furnished and fully equipped cottage is just minutes away on foot from the beach. This home is ideally located near all the hot-spots of Captiva. The master bedroom has a queen-size bed, …see more

from $200 / night

$1,400 / week

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from $200 / night

(1) Excellent 

23

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Captiva Villa is located on a charming private lane in the heart of Captiva, a few minutes stroll from the Gulf beach. This spacious vacation home has 4 bedrooms, 3 baths, and sleeps 8-10 comfortably. The Master Suite has a king bed, TV with VCR & DVD, i pod docking …see more

from $400 / night

$2,800 / week

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Responds fast!
avg. 2 hours 56 minutes

from $400 / night

15

Captiva Island Vacation condo rental

Southwest Gulf Coast / Captiva Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Captiva Island condo at the Hideway. Third floor unit with breathtaking sunrise views overlooking the Bay/ ICW. Just a short 5 min walk to the Beach for sunset, shopping, dinner, and dolphin wayching. 2 bedroom unit. Master has king bed and separate bathroom. Second …see more

from $343 / night

$2,400 / week

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from $343 / night

(9) Excellent 

20

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Ricks Retreat is a charming ground-level home on a beach street located in the village area of Captiva. A short walk to restaurants, shops and galleries, and a 3 minute walk to the most beautiful beach at the end of the sandy lane. Originally built by Bette Davis, Ric …see more

from $225 / night

$1,570 - $3,200 / week

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Responds fast!
avg. 3 hours 42 minutes

from $225 / night

(1) Excellent 

13

Vacation condo in Captiva Island

Southwest Gulf Coast / Captiva Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
$1000 for WEEK OF AUGUST 11-18 Available ONLY for 2017! 2 Bedroom/2 bath condo in South Seas Club at South Seas Island Resort on Captiva Island, FL. Perfect for families - South Seas Club is inside the gates of South Seas Island Resort and fronts the golf course. It ha …see more

from $143 / night

$1,000 / week

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from $143 / night

(5) Very Good 

18

Vacation home with shared pool in Captiva Island

Southwest Gulf Coast / Captiva Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Captiva Retreat (47 Sunset Captiva) is a 2,200 Sq.Ft. detached free-standing home with 2 private bedrooms (2 queens, bunk beds), private den with queen-size wall bed, loft with single bed, and three full bathrooms. It comfortably accommodates 8 guests. If you can' …see more

from $265 / night

$1,850 / week

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from $265 / night

11

Captiva Island Vacation condo rental

Southwest Gulf Coast / Captiva Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
An intimate setting awaits those who enjoy living near the water. This hidden gem near Captiva Village offers the privacy of only 8 units in a well-maintained and managed property, complete with dockage for boaters. Arrive by boat or keep your own within view. This cond …see more

from $258 / night

$1,800 / week

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from $258 / night

15

Home rental in Captiva Island

Southwest Gulf Coast / Captiva Island

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Great house on great street 120 ft to gulf beach 3rd house , no streets to cross!. Casablanca is a newly built, luxury home located on beautiful and private Laika Lane in Captiva Village. Our large home features four bedrooms, four baths plus sleep sofa and has 3500 fee …see more

from $522 / night

$3,660 - $5,900 / week

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from $522 / night

(1) Excellent 

24

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

6 16 7 nights min

  • 6 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to New Latitude ... The premier Captiva Island beach front estate. The home features six bedrooms all with en-suite bathrooms, one half bathroom. New Latitude is the perfect home for family gatherings and once in a lifetime destination vacation. As you pull up a …see more

from $1,490 / night

$9,800 - $23,000 / week

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from $1,490 / night