45 Best Captiva Island Vacation rentals on Holiday Lettings - Cottages

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46 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

$2988 - $5338 / week

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from $427 / night

(6) Very Good 

25

Vacation home with swimming pool 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
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 $443 / night

$3100 - $6400 / week

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from $443 / 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

$1365 - $2450 / week

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from $195 / 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

$1550 - $2750 / week

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from $222 / night

(4) Excellent 

18

Vacation villa in Captiva Island

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
The Coral Reef Beach House is located on tropical North Captiva Island. It is a 4 bedroom 4 bath home professionally decorated in the British Colonial style. 4 levels of living with generous verandas and sun decks. The ground level has a 1200 sqft tumbled stone patio wr …see more

from $451 / night

$3150 - $3570 / week

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from $451 / night

22

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Ask about pets
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 $582 / night

$4070 - $6700 / week

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from $582 / night

(2) 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

$1850 - $2850 / week

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from $265 / night

(1) Excellent 

26

Vacation apartment in Captiva Island

Southwest Gulf Coast / Captiva Island

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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 $543 / night

$3800 - $5600 / week

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from $543 / night

15

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
One Bedroom Bayside Villa - One King Bed plus Sleeper Sofa: From a large screened balcony, guests can revel in tranquil views of the Bayside Marina of Pine Island Sound and the mangrove forest. Located in the South Village area of the resort, they are a short walking di …see more

from $240 / night

$1351 - $3181 / week

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avg. 3 hours 45 minutes

from $240 / night

17

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Gorgeous views of the Pine Island Sound, watch dolphins, sea otters and osprey from your screened in porch. This two bedroom, two bath home is located in the Gulf to Bay community of Captiva Shores. Walk into the bright open living area with tile floors, tropical furnis …see more

from $215 / night

$1500 - $4700 / week

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from $215 / night

14

Vacation apartment in Captiva Island

Southwest Gulf Coast / Captiva Island

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Harbourside Guest Room 2 Queen Beds at the South Seas Island Resort: These guestrooms are located at the prestigious North Pointe, the center of many of the Resorts activities. From the open balcony guests may watch yachts and sailboats in South Seas Marina, or they may …see more

from $258 / night

$1448 - $3352 / week

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Responds fast!
avg. 3 hours 45 minutes

from $258 / 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 $436 / night

$3050 - $3916 / week

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from $436 / 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
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 $393 / night

$2750 - $5200 / week

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from $393 / night

24

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly
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 $486 / night

$3400 - $5800 / week

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from $486 / night

36

Vacation home with swimming pool in Captiva Island

Southwest Gulf Coast / Captiva Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
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 $829 / night

$5800 - $8000 / week

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from $829 / night

21

Apartment rental in Captiva Island

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
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 $279 / night

$1951 - $3300 / week

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from $279 / night

28

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Gentle coastal breezes, warm Gulf water, 2 1/2 miles of driftwood-strewn pristine beachfront, abundant sea and wildlife await you and your guests in the privacy of the small enclave on peaceful Upper Captiva Island. Perfect for disconnecting from everyday interruptions, …see more

from $909 / night

$6363 / week

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Responds fast!
avg. 42 minutes

from $909 / 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

$2800 / week

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Responds fast!
avg. 1 hour 31 minutes

from $400 / night

11

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 $229 / night

$1600 - $2000 / week

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from $229 / night

79

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • 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 $429 / night

$3750 - $4380 / week

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Responds fast!
avg. 2 hours 2 minutes

from $429 / night

12

Apartment rental in Captiva Island

Southwest Gulf Coast / Captiva Island

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
One Bedroom Beach Villa with One Queen Bed plus Sleeper Sofa: From a screen balcony, guests enjoy views of the Gulf of Mexico, pristine white-sand beaches and stunning Captiva sunsets. These villas are situated in the South End of the resort and are aproximately 100 yar …see more

from $331 / night

$1716 - $4658 / week

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Responds fast!
avg. 3 hours 45 minutes

from $331 / 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

$2000 / week

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from $285 / night

16

Apartment rental in Captiva Island with shared pool

Southwest Gulf Coast / Captiva Island

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Harbourside Guestroom One King at South Sea Island Resort: These guestrooms are located at the prestigious North Pointe, the center of many of the Resorts activities. From the open balcony guests may watch yachts and sailboats in South Seas Marina, or they may watch dol …see more

from $258 / night

$1448 - $3352 / week

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Responds fast!
avg. 3 hours 45 minutes

from $258 / night

34

Captiva Island Vacation home rental

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Looking for Magic? This beach home is close to paradise – a beautiful beach just steps from the door, Dolphins and sunsets, peace only disturbed by the waves of the Gulf of Mexico.A magic vacation begins when you cross the gates to a private resort and drive your car in …see more

from $1429 / night

$10000 - $28000 / week

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from $1429 / night

22

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 $368 / night

$2575 - $3901 / week

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from $368 / night

20

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Waterfront Artist Retreat on the water with private dockage. Very unique, totally renovated, State protected home. 3 bedrooms, 2.5 baths. Sleeps 7. High end, commercial appliances. Private swimming pool. Beach access less than a mile. Floating dock for easy acces …see more

from $600 / night

$3800 / week

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from $600 / night

22

Captiva Island Vacation home 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
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 $313 / night

$2190 - $3891 / week

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from $313 / 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 $315 / night

$2200 / week

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from $315 / night

21

Captiva Island Vacation apartment rental

Southwest Gulf Coast / Captiva Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 $258 / night

$1801 - $2600 / week

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from $258 / night

29

Home accommodation in Captiva Island with swimming pool

Southwest Gulf Coast / Captiva Island

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
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 $572 / night

$4000 - $6500 / week

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from $572 / night

26

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 $279 / night

$1951 - $3800 / week

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from $279 / night

28

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 th …see more

from $368 / night

$2575 - $6440 / week

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from $368 / night

(1) Excellent 

24

Apartment rental in Captiva Island

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Bay Breeze CottageComfortable 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 view …see more

from $279 / night

$1951 - $3800 / week

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from $279 / night

28

Vacation apartment 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
Expansive Water Views! This three bedroom three bathroom Captiva Shores townhome features outstanding views of Pine Island Sound and Roosevelt Channel. Watch boats, kayaks, dolphins, manatee and shorebirds from your large private lanai. The large, open living-room fe …see more

from $315 / night

$2200 - $4150 / week

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from $315 / night

27

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
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 $500 / night

$3500 - $5050 / week

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from $500 / night

27

Vacation apartment rental

Southwest Gulf Coast / Captiva Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
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 $386 / night

$2700 - $4100 / week

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from $386 / night

(1) Excellent 

16

Vacation home in Captiva Island

Southwest Gulf Coast / Captiva Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Pet friendly
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 $279 / night

$1951 - $4100 / week

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from $279 / night

25

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 $758 / night

$5301 - $9700 / week

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from $758 / night

22

Vacation home rental

Southwest Gulf Coast / Captiva Island

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Child friendly
Summerhouse- a luxury 8 bedroom/8 bath recently renovated Bayfront Estate with plentiful on-site amenities. Located on Captiva Island in the heart of the village. This 5800 square foot home has been designed with a coastal chic theme and features white marble bathrooms …see more

from $1850 / night

$12950 / week

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from $1850 / night

22

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 th …see more

from $368 / night

$2575 - $3800 / week

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from $368 / night

1