45 Best Captiva Island Vacation rentals on Holiday Lettings - Cottages

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1,774 Vacation rentals

(2) Excellent 

36

Vacation home rental

Southwest Gulf Coast / Captiva Island

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $333 / night

$1,988 - $5,338 / week

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from $333 / night

27

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Escape your worries in this Captiva Island beach bungalow. Enjoy the bright and cheery island décor throughout this three bedroom two bath pool home. Surrounded by bright tropical vegetation this home offers a perfect location to the Heart of Captiva as well as ultima …see more

from $435 / night

$3,045 / week

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from $435 / night

20

Apartment rental in Captiva Island

Southwest Gulf Coast / Captiva Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
This 3 bedroom townhome with 2 1/2 baths has everything you need for the perfect beach vacation. Relax to bay views from your screened lanai opening off the open floor plan living area-- including a comfortable seating area with a flat screen smart TV and DVD, a large …see more

from $306 / night

$2,142 / week

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from $306 / night

19

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Beach Villa Sunset Dreams is a recently richly remodeled and appointed townhome with tropical beach décor for an unforgettable family vacation. The Villa is unique with awe inspiring direct gulf views and amazing sunsets, as well as sunrise views over the bay. The prope …see more

from $602 / night

$4,214 / week

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from $602 / night

(1) Excellent 

27

Apartment rental in Captiva Island

Southwest Gulf Coast / Captiva Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
Bay Breeze Cottage Comfortable poolside cottage offering cooling bay breezes and glorious bay views from nearly every room. This 3 bedroom cottage with 2 1/2 baths has a recently renovated kitchen to offer everything you need for a great beach vacation. Relax to bay vi …see more

from $316 / night

$2,212 / week

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from $316 / night

86

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. 1 hour 22 minutes

from $600 / night

26

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Enjoy brilliant sunsets over the sapphire waters of the Gulf of Mexico and ideal deep water direct access along Roosevelt Channel from this recently updated unit at Captiva Shores. This bright updated beach condo has direct Gulf views. The open kitchen has new white ca …see more

from $214 / night

$1,498 / week

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from $214 / night

23

Vacation home rental

Southwest Gulf Coast / Captiva Island

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Private garden
Paradise Awaits at Beach Destiny! This 4 bedroom, 5.5 bathroom, oceanfront, luxury home is the perfect spot for a dream vacation. The large living room features stunning views of the Gulf, a large flat screen TV, a huge sectional couch and sliding glass doors onto th …see more

from $1,166 / night

$8,162 / week

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from $1,166 / 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

(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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Responds fast!
avg. 48 minutes

from $1,490 / 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

(7) Very Good 

30

Vacation home with swimming pool in Captiva Island

Southwest Gulf Coast / Captiva Island

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
A dream home for a dream vacation. This 5 bedroom 6 bathroom has everything you would want for an outstanding vacation. Gorgeous views of Pine Island sound, a large screened in pool, u-shaped boat dock in your backyard, a tiled sun deck with great views and a short st …see more

from $487 / night

$3,409 / week

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from $487 / night

(1) Excellent 

24

Vacation apartment in Captiva Island

Southwest Gulf Coast / Captiva Island

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Sapphire blue water, white sandy beaches, amazing sunsets from your living-room and a luxury four bedroom villa. Everything you need for the perfect friends and family vacation. “Conch” features tropical colors in this remodeled spacious villa. Walk into the living-ro …see more

from $598 / night

$4,186 / week

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from $598 / night

22

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Lollipop, the perfect Captiva vacation home. Central to Captiva village this three bedroom three and ½ bath pool home offers the perfect escape for a relaxing vacation. There are so many great features to this home, cathedral ceilings, screened in porch, updated moder …see more

from $479 / night

$3,353 / week

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from $479 / night

44

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
If you are looking for amazing views, a great pool, great fishing, boating, a place to sleep and value savings, Sea Otter is a great option. It offers a great location but is a no frills lodging experience. Furnishings, décor, fixtures and appliances are dated and meet …see more

from $534 / night

$3,738 / week

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from $534 / 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

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

35

Apartment rental in Captiva Island

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Listen to the sounds of the waves from your screened in porch while enjoying world renowned sunsets. This three bedroom two and one half bath Gulf Front Captiva home has everything you want to make this a vacation of a lifetime. Walk into the bright great room featurin …see more

from $401 / night

$2,807 / week

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from $401 / 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 - $2,751 / week

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from $222 / 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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from $225 / night

23

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Car not necessary
Located within the world class South Seas resort, including four miles of private beach, top rated golfing, pristine blue waters, this unit is truly one of a kind. And it is reasonably priced! Here are some more details: - 3rd floor unit possessing gorgeous panoramic …see more

from $199 / night

$1,393 / week

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from $199 / night

27

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Amazing Location! This five bedroom, five bathroom pool home is central to Captiva Village, marinas, restaurants, shops and live music. A chef’s kitchen, open living and dining room, high ceilings, and a screened in pool make this the perfect home for a great vacati …see more

from $640 / night

$4,480 / week

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from $640 / night

35

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Let your troubles melt away in this luxury three bedroom three bath condo with a den. Relax on the spacious lanai with sweeping direct bay views. The large living room has beautiful views, tile floors, built in cabinets and double tray ceilings with wood accents. The …see more

from $442 / night

$3,094 / week

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from $442 / night

(1) Excellent 

26

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Private garden
Direct Gulf views, lush tropical landscape, a great location and a charming beach cottage are all the ingredients you need for an amazing Captiva vacation. This is a historical Cape Cod style ground level home with older finishes throughout including the original kitch …see more

from $306 / night

$2,142 / week

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from $306 / night

40

Home accommodation in Captiva Island with swimming pool

Southwest Gulf Coast / Captiva Island

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Great Location, Amazing house, Stunning Views. Located in the heart of Captiva Island this five bedroom, four bathroom pool home is the perfect spot for an amazing vacation. Walk into the living area with small table, sectional couch, comfortable chairs and a flat sc …see more

from $629 / night

$4,403 / week

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from $629 / 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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Responds fast!
avg. 3 hours 12 minutes

from $200 / night

30

Vacation home with swimming pool in Captiva Island

Southwest Gulf Coast / Captiva Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Stunning Gulf Front Beauty! Walk out the back door and you’re on the beach! This four bedroom three and ½ bathroom home is the perfect escape for a relaxing beach vacation. The large living room features a flat screen TV, a fireplace, comfortable seating, a desk area …see more

from $911 / night

$6,377 / week

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from $911 / night

(5) Very Good 

18

Vacation home 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 $279 / night

$1,950 - $3,350 / week

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from $279 / night

36

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
A gorgeous 5BR/5BA Mediterranean style beach home w private pool, 11514 Andy Rosse Lane. …see more

from $1,000 / night

$5,000 - $7,300 / week

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from $1,000 / 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

(2) Very Good 

32

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Location! Location! Gulf front with sparkling Captiva beach right out the front door, yet it is a short walk to the village to visit your favorite bar or restaurant. This is the house that has it all -- close to the village, but far enough away to enjoy the quiet and pr …see more

from $896 / night

$6,272 / week

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from $896 / 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

21

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Watch the amazing sunset from your own screened in Lanai directly across from the beach. The three bedroom three bath Gulf Front Captiva townhome has everything you want to make this a vacation of a lifetime. Walk into the bright great room featuring direct views of the …see more

from $405 / night

$2,835 / week

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from $405 / night

23

Vacation apartment accommodation

Southwest Gulf Coast / Captiva Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
I bought the condo within 15 minutes of seeing it because the views are breathtaking. The main living area looks out on Redfish Pass, the Gulf of Mexico, north Captiva Island and Pine Island sound. We can hear the dolphins blowing while they jump along the fishing bo …see more

from $343 / night

$2,400 - $4,500 / week

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from $343 / night

24

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our Tropical Captiva Island Vacation home-away-from-home. We decided to name our home Sanga Na Langa which means No Worries in the Fijian language. Nothing is more fitting after you experience a week or longer at the home and on Captiva Island. Our vacation r …see more

from $500 / night

$3,000 - $6,000 / week

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Responds fast!
avg. 48 minutes

from $500 / night

23

Vacation apartment rental

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Watch dolphins, sea otters and osprey from you’re screened in porch overlooking Pine Island Sound. This three bedroom two and one half bath home has beautiful finishes throughout. Walk into the bright open living area with tropical and elegant furnishings. Views of Pi …see more

from $424 / night

$2,968 / week

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from $424 / night

27

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Watch dolphins, sea otters and osprey from your screened in porch overlooking Pine Island Sound. This three bedroom two and one half bath home has beautiful finishes throughout. Walk into the bright open living area with tropical and elegant furnishings. Views of Pine …see more

from $306 / night

$2,142 / week

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from $306 / 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 - $4,500 / week

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Responds fast!
avg. 3 hours 17 minutes

from $522 / night

28

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Sapphire blue water, white sandy beaches just steps from your front door and a luxury villa. Everything you need for the perfect friends and family vacation. Donax Beach Villa offers spacious rooms, rich colorful décor and comfortable living. Walk into the professi …see more

from $558 / night

$3,906 / week

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from $558 / night

24

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Direct Gulf Front Views! This three bedroom two and one half bath townhome is centrally located on Captiva Island. Amazing views from the living room and front porch! Walk into the bright, open living room that overlooks the Gulf of Mexico. The large kitchen feature …see more

from $542 / night

$3,794 / week

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from $542 / night