Photo by Anthony Ball

Captiva Island holiday rentals

We found 2,349 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$1,567
for 7 nights, 1 room
S$224 per night
includes taxes & fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Living & Dining
Location
Kitchen
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$4,242
for 7 nights, 1 home
S$606 per night
includes taxes & fees
PERFECT FAMILY GETAWAY - 3 Bedroom / 2 ½ Bath w/ 60' Boat Dock & Private Pool
Pool
Dining
Living area
Exterior
Exceptional
(30 reviews)

Island Getaway Florida

Saint James City

11% off
S$3,370
for 7 nights, 1 home
S$481 per night
includes taxes & fees
Island Getaway Florida
Kitchen / Dining
Front Entry
Pool
Family Room
Exceptional
(15 reviews)

Open Breeze - Luxury Near Beach Home on Captiva

Captiva

7% off
S$11,453
for 7 nights, 1 home
S$1,636 per night
includes taxes & fees
Open Breeze - Luxury Near Beach Home on Captiva
Pool
So close to our beautiful beach.
Living area
Interior
Exceptional
(48 reviews)

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

Captiva

9% off
S$5,281
for 7 nights, 1 home
S$754 per night
includes taxes & fees
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
Marina
Outdoor dining
Exterior
Room
Exceptional
(10 reviews)

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

Matlacha

7% off
S$1,703
for 7 nights, 1 cottage
S$243 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$2,506
for 7 nights, 1 home
S$358 per night
includes taxes & fees
Turtle House - Waterfront with Dock - Unbelievable Sunset View
Pool
Exterior
Private kitchen
Living area
Exceptional
(5 reviews)

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

Captiva

8% off
S$6,574
for 7 nights, 1 home
S$939 per night
includes taxes & fees
Two minute walk to a soft sandy beach with some of the best shelling in the US.
double high ceilings and barn doors in loft kids room.
Games on "Beachy" Backard
Living Room double ceiling high
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$6,121
for 7 nights, 1 home
S$874 per night
includes taxes & fees
Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week
Marina
Interior
Interior
Private kitchen
Exceptional
(5 reviews)

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

Matlacha

7% off
S$1,772
for 7 nights, 1 home
S$253 per night
includes taxes & fees
Cozy fishing cottage on canal in Matlacha - 2 bedrooms and large outdoor space
Private kitchen
Beach
Dining
Living area
Exceptional
(38 reviews)

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

Captiva

7% off
S$5,307
for 7 nights, 1 home
S$758 per night
includes taxes & fees
Spectacular beach front views with a short walk to members only beach
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.
Master bedroom (Queen), walk out to lanai
Oversized Salt water pool with spa
Pool 80+ degrees
Spa 100+ degrees, on demand
Front door enters into dining room, seating for 6+ guests
Fully functional open kitchen
Exceptional
(48 reviews)

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

Bokeelia

6% off
S$2,753
for 7 nights, 1 home
S$393 per night
includes taxes & fees
Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife
Terrace/patio
Kitchen view from living room
Property grounds
Queen/master bedroom with bathroom ensuite
Exceptional
(12 reviews)

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

Saint James City

8% off
S$1,777
for 7 nights, 1 home
S$254 per night
includes taxes & fees
LOCATION Cozy bungalow on Monroe Canal, the most entertaining / traveled canal
Living area
Dining
Living area
Room
Exceptional
(34 reviews)

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

Captiva

7% off
S$4,456
for 7 nights, 1 home
S$637 per night
includes taxes & fees
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
Dining Nook in Kitchen
Another Lanai View
Sports court
Lovely and Well Equipped Kitchen
Exceptional
(78 reviews)

Gulf Front Sanibel Condo with Spectacular Views

Sanibel

8% off
S$6,409
for 7 nights, 1 apartment
S$916 per night
includes taxes & fees
Gulf Front Sanibel Condo with Spectacular Views
Interior
Beach
Pool
Room
Exceptional
(65 reviews)

⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️

Captiva

15% off
S$5,099
for 7 nights, 1 apartment
S$728 per night
includes taxes & fees
⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️
Living area
Exterior
Interior
Living area
Exceptional
(45 reviews)

⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️

Captiva

15% off
S$5,061
for 7 nights, 1 apartment
S$723 per night
includes taxes & fees
⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️
Interior
Living area
Room
Dining
Exceptional
(14 reviews)

Beachfront Condo, 2bd/2bath Pet-Friendly

Sanibel

7% off
S$2,887
for 7 nights, 1 apartment
S$412 per night
includes taxes & fees
Beachfront Condo, 2bd/2bath Pet-Friendly
Living area
Living area
Property grounds
Exterior
Excellent
(24 reviews)

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

Captiva

8% off
S$4,357
for 7 nights, 1 cottage
S$622 per night
includes taxes & fees
Spacious "Crab Cakes" Cottage on N. Captiva with GolfCart, Starlink and new AC
Private kitchen
Beach
Dining
Living area
Exceptional
(126 reviews)

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

Captiva

8% off
S$4,526
for 7 nights, 1 apartment
S$647 per night
includes taxes & fees
Stunning Modern beach front unit - completely renovated! Includes golf cart!
Welcome to Loggerhead Cay!
Large and comfortable living room with full size pull out bed
Large living room
Spacious, light-filled living space with coastal-inspired decor
Exceptional
(10 reviews)

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

Sanibel

8% off
S$3,867
for 7 nights, 1 apartment
S$552 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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