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Captiva Island holiday rentals

We found 2,352 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Captiva Island

Showing deals for:13 Nov - 20 Nov

Property grounds
Room
Outdoor dining
Private kitchen
Exceptional
(60 reviews)

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Matlacha

8% off
S$1,544
for 7 nights, 1 room
S$221 per night
includes taxes & fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Living area
Dining
Exterior
Marina
Exceptional
(30 reviews)

Island Getaway Florida

Saint James City

11% off
S$3,413
for 7 nights, 1 home
S$488 per night
includes taxes & fees
Island Getaway Florida
Kitchen
Location
Living & Dining
Top deck lanai
Exceptional
(31 reviews)

PERFECT FAMILY GETAWAY - 3 Bedroom / 2 ½ Bath w/ 60' Boat Dock & Private Pool

Saint James City

8% off
S$4,248
for 7 nights, 1 home
S$607 per night
includes taxes & fees
PERFECT FAMILY GETAWAY - 3 Bedroom / 2 ½ Bath w/ 60' Boat Dock & Private Pool
Family Room
Front Entry
Pool
Kitchen / Dining
Exceptional
(15 reviews)

Open Breeze - Luxury Near Beach Home on Captiva

Captiva

7% off
S$11,339
for 7 nights, 1 home
S$1,620 per night
includes taxes & fees
Open Breeze - Luxury Near Beach Home on Captiva
Property grounds
So close to our beautiful beach.
Pool
Interior
Exceptional
(48 reviews)

Upgraded beach house located just steps away from the beach. Pool and Hot tub.

Captiva

9% off
S$5,209
for 7 nights, 1 home
S$744 per night
includes taxes & fees
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
Exterior
Outdoor dining
Property grounds
Room
Exceptional
(10 reviews)

Orange You Glad Cottage - A Fisherman’s Paradise in sunny Matlacha

Matlacha

7% off
S$1,672
for 7 nights, 1 cottage
S$239 per night
includes taxes & fees
Orange You Glad Cottage - A Fisherman’s Paradise in sunny Matlacha
Exterior
Outdoor dining
Living area
Dining
Exceptional
(7 reviews)

Turtle House - Waterfront with Dock - Unbelievable Sunset View

Matlacha

16% off
S$2,480
for 7 nights, 1 home
S$354 per night
includes taxes & fees
Turtle House - Waterfront with Dock - Unbelievable Sunset View
“Island nights are better by the fire table 💛🏝️”
“Pulling up to paradise… and the fun starts now! 🏝️✨”
Experience the seamless flow of space in our open floor plan, where each room gracefully transitions into the next. A design that fosters connection, natural light, and an expansive sense of freedom. Welcome to a living space that feels as open as the poss
Dive into pure bliss in our outdoor paradise. Immerse yourself in the warmth of luxury with an inviting heated pool and spa that redefine relaxation. Let the tranquil waters and tropical surroundings transport you to a haven of serenity
Exceptional
(23 reviews)

Pet-Friendly Island Home | Pool, Hot Tub + Cart

Captiva

7% off
S$6,954
for 7 nights, 1 home
S$993 per night
includes taxes & fees
Pet-Friendly Island Home | Pool, Hot Tub + Cart
Dining
Interior
Exterior detail
Room
Exceptional
(61 reviews)

Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.

Bokeelia

8% off
S$817
for 7 nights, 1 cottage
S$117 per night
includes taxes & fees
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
Private kitchen
Exterior
Living area
Dining
Exceptional
(5 reviews)

Two minute walk to a soft sandy beach with some of the best shelling in the US.

Captiva

8% off
S$6,485
for 7 nights, 1 home
S$926 per night
includes taxes & fees
Two minute walk to a soft sandy beach with some of the best shelling in the US.
Room
Interior
Marina
Interior
Exceptional
(5 reviews)

Cozy fishing cottage on canal in Matlacha - 2 bedrooms and large outdoor space

Matlacha

7% off
S$1,736
for 7 nights, 1 home
S$248 per night
includes taxes & fees
Cozy fishing cottage on canal in Matlacha - 2 bedrooms and large outdoor space
Terrace/patio
Kitchen view from living room
Living area
Queen/master bedroom with bathroom ensuite
Exceptional
(11 reviews)

LOCATION Cozy bungalow on Monroe Canal, the most entertaining / traveled canal

Saint James City

7% off
S$1,808
for 7 nights, 1 home
S$258 per night
includes taxes & fees
LOCATION Cozy bungalow on Monroe Canal, the most entertaining / traveled canal
Fully functional open kitchen
Oversized Salt water pool with spa
Pool 80+ degrees
Spa 100+ degrees, on demand
Master bedroom (Queen), walk out to lanai
Fully functional kitchen, opens to living room
Exceptional
(48 reviews)

Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife

Bokeelia

6% off
S$2,684
for 7 nights, 1 home
S$383 per night
includes taxes & fees
Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife
Dining
Games on "Beachy" Backard
double high ceilings and barn doors in loft kids room.
Double size lot in secluded cul de sac
Exceptional
(54 reviews)

Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week

Captiva

8% off
S$6,037
for 7 nights, 1 home
S$862 per night
includes taxes & fees
Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week
Living area
Beach
Private kitchen
Dining
Exceptional
(38 reviews)

Spectacular beach front views with a short walk to members only beach

Captiva

7% off
S$5,299
for 7 nights, 1 home
S$757 per night
includes taxes & fees
Spectacular beach front views with a short walk to members only beach
Living area
Dining
Exterior
Room
Exceptional
(33 reviews)

Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!

Captiva

7% off
S$4,449
for 7 nights, 1 home
S$636 per night
includes taxes & fees
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
Sports court
Another Lanai View
Beach Path
Dining Nook in Kitchen
Exceptional
(78 reviews)

Gulf Front Sanibel Condo with Spectacular Views

Sanibel

8% off
S$6,400
for 7 nights, 1 apartment
S$914 per night
includes taxes & fees
Gulf Front Sanibel Condo with Spectacular Views
Interior
Beach
Interior
Pool
Exceptional
(65 reviews)

⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️

Captiva

15% off
S$5,052
for 7 nights, 1 apartment
S$722 per night
includes taxes & fees
⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️
Pool
Exterior
Interior
Living area
Exceptional
(45 reviews)

⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️

Captiva

15% off
S$5,015
for 7 nights, 1 apartment
S$716 per night
includes taxes & fees
⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️
Room
Living area
Interior
Dining
Exceptional
(14 reviews)

Beachfront Condo, 2bd/2bath Pet-Friendly

Sanibel

8% off
S$2,847
for 7 nights, 1 apartment
S$407 per night
includes taxes & fees
Beachfront Condo, 2bd/2bath Pet-Friendly
Property grounds
Living area
Private kitchen
Exterior
Excellent
(24 reviews)

Spacious "Crab Cakes" Cottage on N. Captiva with GolfCart, Starlink and new AC

Captiva

8% off
S$4,298
for 7 nights, 1 cottage
S$614 per night
includes taxes & fees
Spacious "Crab Cakes" Cottage on N. Captiva with GolfCart, Starlink and new AC
Living area
Beach
Dining
Private kitchen
Exceptional
(125 reviews)

Stunning Modern beach front unit - completely renovated! Includes golf cart!

Captiva

8% off
S$4,490
for 7 nights, 1 apartment
S$641 per night
includes taxes & fees
Stunning Modern beach front unit - completely renovated! Includes golf cart!
Spacious, light-filled living space with coastal-inspired decor
Large and comfortable living room with full size pull out bed
Loggerhead Cay aerial view
Welcome to Loggerhead Cay!
Exceptional
(10 reviews)

Loggerhead Cay 584 Beachside Condo with Partial Gulf and Pool Views!

Sanibel

8% off
S$3,815
for 7 nights, 1 apartment
S$545 per night
includes taxes & fees
Loggerhead Cay 584 Beachside Condo with Partial Gulf and Pool Views!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Delight in the waterfront landscape of Captiva Island

The island views and other outdoor surroundings create an inviting atmosphere in Captiva Island. Well known for its dolphin watching, kayaking and fishing, this relaxing city won't disappoint. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Captiva Island

Are you hoping to find top things to see and do during your stay? Travellers enjoy Captiva Island for its dolphin viewing, kayaking and fishing. Venture out of your holiday home and check out everything that Captiva Island has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Sun Splash Water Park (15.5 mi / 24.9 km)
  • Dunes Golf and Tennis Club (10.7 mi / 17.3 km)
  • Sanibel Island Golf Club (10.9 mi / 17.6 km)
  • Palmetto-Pine Country Club (13.7 mi / 22 km)
  • Coral Oaks Golf Course (14.8 mi / 23.9 km)
  • Mike Greenwell's Bat-A-Ball & Family Fun Park (16.4 mi / 26.3 km)

Exploring the beaches and other natural features in Captiva Island

Captiva Island is famous for its island views and breathtaking sunsets. Whether you're looking for fun outdoor activities or just want to take in the scenery, Captiva Island is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Captiva Beach (1.7 mi / 2.7 km)
  • Turner Beach (3.2 mi / 5.2 km)
  • Blind Pass Beach (3.4 mi / 5.4 km)
  • North Captiva Island Beach (3.7 mi / 5.9 km)
  • Bowman's Beach (5.4 mi / 8.6 km)
  • J. N. Ding Darling National Wildlife Refuge (6.6 mi / 10.6 km)

Frequently asked questions

What is the most popular type of holiday rental accommodation in Captiva Island?
The most popular types of holiday rentals in Captiva Island are condos. Looking for something different? Vrbo has many options to match the diverse needs of our guests, so you'll see holiday properties in all shapes and sizes, and for all budgets. The ideal home away from home is waiting for you — find yours today.
How much does it cost to rent a holiday rental in Captiva Island?
Property type, length of stay and time of year are some factors that can influence the price of a holiday home. Simply click on your travel dates to find your dream escape. From cosy chalets to expansive luxury villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Captiva Island?
Prices for beach houses in Captiva Island differ depending on the type and size of the property and when you're travelling. Simply enter your dates of travel into Vrbo and how many guests to view your rental options and prices. From there you can use our filters to narrow your search by amenities, nearby activities, ratings and more.
What are popular rental amenities in Captiva Island?
When it comes to rental amenities that people are looking for in Captiva Island, a barbecue grill, a beach view and a nearby waterfront rank highest. With Vrbo holiday rentals, you'll enjoy choices to suit your taste and style, whether you're going on a holiday with family members, friends or even pets.
Can I find two-bedroom holiday rentals in Captiva Island?
You can pick from three two-bedroom holiday rentals in Captiva Island. Give your little ones the second room or maybe fill it with a couple of your best friends. There's a comfy spot for whoever's fortunate enough to be joining in on the fun.
How old do you have to be to rent a holiday rental in Captiva Island?
The minimum age can vary across properties on Vrbo, so be sure to check the rules of the holiday home in Captiva Island you're considering. But typically, it's 16, 18 or 21.
How long can I rent a holiday rental in Captiva Island for?
It's down to the Captiva Island property. To see all available options offering extended stays, just enter your dates and number of people into Vrbo's search page. You can enjoy having the entire property to yourself, along with comforts such as air conditioning, a fully-equipped kitchen and a yard where the kids can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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