45 Best Captiva Island Vacation rentals on Holiday Lettings - Cottages

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49 Vacation rentals

Travelers going to Captiva Island are booking December dates now. Secure your vacation rental today and have the perfect trip.

(1) 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

$2988 - $5338 / week

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from $427 / night

(2) Excellent 

26

Southwest Gulf Coast / Captiva Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $225 / night

$1570 - $2650 / week

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from $225 / night

17

Southwest Gulf Coast / Captiva Island

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Ask about children

 …see more

from $475 / night

$2607 - $7528 / week

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from $475 / night

(4) Excellent 

24

Southwest Gulf Coast / Captiva Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool

 …see more

from $290 / night

$2030 / week

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from $290 / night

15

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $386 / night

$2143 - $7092 / week

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from $386 / night

10

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

 …see more

from $195 / night

$1365 - $3080 / week

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from $195 / night

14

Southwest Gulf Coast / Captiva Island

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $240 / night

$1351 - $3352 / week

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from $240 / night

18

Southwest Gulf Coast / Captiva Island

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

 …see more

from $450 / night

$2850 - $5060 / week

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from $450 / night

(4) Excellent 

16

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $285 / night

$2000 - $3600 / week

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from $285 / night

15

Southwest Gulf Coast / Captiva Island

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $240 / night

$1351 - $3181 / week

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from $240 / night

11

Southwest Gulf Coast / Captiva Island

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $207 / night

$1445 - $2145 / week

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from $207 / night

16

Southwest Gulf Coast / Captiva Island

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $240 / night

$1351 - $3352 / week

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from $240 / night

17

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $414 / night

$2288 - $7354 / week

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from $414 / night

20

Southwest Gulf Coast / Captiva Island

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $600 / night

$3800 / week

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from $600 / night

66

Southwest Gulf Coast / Captiva Island

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Ask about pets

 …see more

from $429 / night

$3750 - $4380 / week

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from $429 / night

12

Southwest Gulf Coast / Captiva Island

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $249 / night

$1399 - $4658 / week

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from $249 / night

17

Southwest Gulf Coast / Captiva Island

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $215 / night

$1500 - $4700 / week

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from $215 / night

22

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $368 / night

$2575 - $3900 / week

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from $368 / night

28

Southwest Gulf Coast / Captiva Island

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning

 …see more

from $900 / night

$6300 - $6363 / week

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from $900 / night

(1) Excellent 

23

Southwest Gulf Coast / Captiva Island

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $400 / night

$2800 / week

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from $400 / night

34

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $1858 / night

$13000 - $28000 / week

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from $1858 / night

17

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $386 / night

$2143 - $7092 / week

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from $386 / night

24

Southwest Gulf Coast / Captiva Island

Studio 12 7 nights min

  • Studio
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

 …see more

from $486 / night

$3400 - $5800 / week

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from $486 / night

22

Southwest Gulf Coast / Captiva Island

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $436 / night

$3050 - $3915 / week

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from $436 / night

25

Southwest Gulf Coast / Captiva Island

Studio 10 7 nights min

  • Studio
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $715 / night

$5000 - $7500 / week

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from $715 / night

(6) Very Good 

25

Southwest Gulf Coast / Captiva Island

Studio 12 7 nights min

  • Studio
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $443 / night

$3100 - $6400 / week

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from $443 / night

15

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $414 / night

$2288 - $7354 / week

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from $414 / night

(1) Excellent 

16

Southwest Gulf Coast / Captiva Island

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Pet friendly

 …see more

from $279 / night

$1950 - $4100 / week

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from $279 / night

14

Southwest Gulf Coast / Captiva Island

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $322 / night

$1716 - $4658 / week

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from $322 / night

(1) Excellent 

24

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $288 / night

$2010 - $3800 / week

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from $288 / night

29

Southwest Gulf Coast / Captiva Island

Studio 12 7 nights min

  • Studio
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $572 / night

$4000 - $6500 / week

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from $572 / night

17

Southwest Gulf Coast / Captiva Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from $229 / night

$1600 - $2800 / week

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from $229 / night

24

Southwest Gulf Coast / Captiva Island

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $393 / night

$2750 - $5150 / week

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from $393 / night

25

Southwest Gulf Coast / Captiva Island

Studio 12 7 nights min

  • Studio
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $758 / night

$5300 - $9700 / week

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from $758 / night

29

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $414 / night

$2895 - $7390 / week

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from $414 / night

22

Southwest Gulf Coast / Captiva Island

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $313 / night

$2190 - $3890 / week

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from $313 / night

27

Southwest Gulf Coast / Captiva Island

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $500 / night

$3500 - $8965 / week

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from $500 / night

28

Southwest Gulf Coast / Captiva Island

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $315 / night

$2200 - $4150 / week

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from $315 / night

15

Southwest Gulf Coast / Captiva Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $315 / night

$2200 / week

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from $315 / night

36

Southwest Gulf Coast / Captiva Island

Studio 10 7 nights min

  • Studio
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $829 / night

$5800 - $8000 / week

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from $829 / night

1