Photo by Anthony Ball

Captiva Island holiday rentals

We found 2,315 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Captiva Island

Showing deals for:27 Nov - 4 Dec

Property grounds
Room
Private kitchen
Interior
Exceptional
(60 reviews)

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

Matlacha

8% off
S$1,555
for 7 nights, 1 room
S$222 per night
includes taxes & fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Room
Outdoor dining
Property grounds
Exterior
Exceptional
(11 reviews)

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

Matlacha

7% off
S$1,690
for 7 nights, 1 cottage
S$241 per night
includes taxes & fees
Orange You Glad Cottage - A Fisherman’s Paradise in sunny Matlacha
Room
Interior
Dining
Exterior detail
Exceptional
(61 reviews)

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

Bokeelia

8% off
S$811
for 7 nights, 1 cottage
S$116 per night
includes taxes & fees
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
Living Room double ceiling high
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$6,491
for 7 nights, 1 home
S$927 per night
includes taxes & fees
Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week
Interior
So close to our beautiful beach.
Living area
Pool
Exceptional
(48 reviews)

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

Captiva

9% off
S$5,680
for 7 nights, 1 home
S$811 per night
includes taxes & fees
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
Private kitchen
Outdoor dining
Exterior
Dining
Exceptional
(7 reviews)

Turtle House - Waterfront with Dock - Unbelievable Sunset View

Matlacha

16% off
S$2,487
for 7 nights, 1 home
S$355 per night
includes taxes & fees
Turtle House - Waterfront with Dock - Unbelievable Sunset View
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$4,722
for 7 nights, 1 home
S$675 per night
includes taxes & fees
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
Pool
Dining
Marina
Living area
Exceptional
(31 reviews)

Island Getaway Florida

Saint James City

11% off
S$3,344
for 7 nights, 1 home
S$478 per night
includes taxes & fees
Island Getaway Florida
Private kitchen
Marina
Living area
Room
Exceptional
(8 reviews)

3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat

Saint James City

6% off
S$4,177
for 7 nights, 1 home
S$597 per night
includes taxes & fees
3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat
Dining
Exterior
Living area
Private kitchen
Exceptional
(5 reviews)

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

Captiva

8% off
S$6,524
for 7 nights, 1 home
S$932 per night
includes taxes & fees
Two minute walk to a soft sandy beach with some of the best shelling in the US.
Welcome to the heart of Green Tortuga, where the kitchen, dining, and living room converge in a harmonious dance of open space. This seamless design invites connection, conversation, and the free flow of moments in a space where every corner feels like hom
“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$8,001
for 7 nights, 1 home
S$1,143 per night
includes taxes & fees
Pet-Friendly Island Home | Pool, Hot Tub + Cart
Master bedroom
Location
Kitchen
Top deck lanai
Exceptional
(32 reviews)

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

Saint James City

8% off
S$4,210
for 7 nights, 1 home
S$601 per night
includes taxes & fees
PERFECT FAMILY GETAWAY - 3 Bedroom / 2 ½ Bath w/ 60' Boat Dock & Private Pool
Interior
Interior
Room
Marina
Exceptional
(5 reviews)

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

Matlacha

7% off
S$1,758
for 7 nights, 1 home
S$251 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
Queen/master bedroom with bathroom ensuite
Property grounds
Exceptional
(13 reviews)

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

Saint James City

8% off
S$1,918
for 7 nights, 1 home
S$274 per night
includes taxes & fees
LOCATION Cozy bungalow on Monroe Canal, the most entertaining / traveled canal
Living area
Gorgeous 3 bedroom penthouse beach villa
Gorgeous 3 bedroom penthouse beach villa
Patio overlooking Gulf of Mexico
Exceptional
(5 reviews)

Beach Villa 2638 | Executive Gulf Front Residence on Captiva Island

Captiva

7% off
S$5,998
for 7 nights, 1 apartment
S$857 per night
includes taxes & fees
Beach Villa 2638 | Executive Gulf Front Residence on Captiva Island
Living area
Living area
Living area
Living area
Exceptional
(65 reviews)

⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️

Captiva

15% off
S$6,172
for 7 nights, 1 apartment
S$882 per night
includes taxes & fees
⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️
Dining
Living area
Living area
Dining
Exceptional
(46 reviews)

⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️

Captiva

15% off
S$6,070
for 7 nights, 1 apartment
S$867 per night
includes taxes & fees
⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️
Backyard fountain. The soothing sound of falling waters fills pool deck & yard.
Magnificent sunset views from screened porch overlooking pool and golf course.
Dolphins' fountain in front yard.
MASTER SUITE - King-size bed, balcony overlooking pool and golf course
Exceptional
(112 reviews)

SANIBEL SUN CASTLE Splendid home, heated pool, great location, bike to beach.

Sanibel

8% off
S$6,687
for 7 nights, 1 home
S$955 per night
includes taxes & fees
SANIBEL SUN CASTLE Splendid home, heated pool, great location, bike to beach.
Private, second-level screened patio with view of nicely landscaped garden area.
Private access path to Sanibel’s famous Gulf of Mexico beach.
Living room - all the comforts of home.  Cable TV, Wi-Fi.
Just steps to the beach or our pool as you relax in this tropical setting.
Exceptional
(50 reviews)

Tropical Garden Condo Just Steps to Sanibel Beach

Sanibel

8% off
S$4,319
for 7 nights, 1 apartment
S$617 per night
includes taxes & fees
Tropical Garden Condo Just Steps to Sanibel Beach
  • 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)
  • Mike Greenwell's Bat-A-Ball & Family Fun Park (16.4 mi / 26.3 km)
  • Sanibel Captiva Conservation Foundation (8.6 mi / 13.9 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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