Photo by Anthony Ball

Captiva Island holiday rentals

We found 2,326 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Captiva Island

Showing deals for:11 Dec - 18 Dec

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

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

Matlacha

8% off
S$1,530
for 7 nights, 1 room
S$219 per night
includes taxes & fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
double high ceilings and barn doors in loft kids room.
Games on "Beachy" Backard
Double size lot in secluded cul de sac
Living Room double ceiling high
Exceptional
(54 reviews)

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

Captiva

8% off
S$6,627
for 7 nights, 1 home
S$947 per night
includes taxes & fees
Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week
Living area
So close to our beautiful beach.
Pool
Property grounds
Exceptional
(48 reviews)

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

Captiva

9% off
S$5,421
for 7 nights, 1 home
S$774 per night
includes taxes & fees
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
Room
Dining
Living area
Exterior
Exceptional
(34 reviews)

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

Captiva

8% off
S$4,632
for 7 nights, 1 home
S$662 per night
includes taxes & fees
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
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
“Pulling up to paradise… and the fun starts now! 🏝️✨”
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
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$6,956
for 7 nights, 1 home
S$994 per night
includes taxes & fees
Pet-Friendly Island Home | Pool, Hot Tub + Cart
Pool
Exterior
Private kitchen
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$6,462
for 7 nights, 1 home
S$923 per night
includes taxes & fees
Two minute walk to a soft sandy beach with some of the best shelling in the US.
Marina
Outdoor dining
Property grounds
Exterior
Exceptional
(11 reviews)

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

Matlacha

7% off
S$1,657
for 7 nights, 1 cottage
S$237 per night
includes taxes & fees
Orange You Glad Cottage - A Fisherman’s Paradise in sunny Matlacha
Exterior
Outdoor dining
Dining
Living area
Exceptional
(7 reviews)

Turtle House - Waterfront with Dock - Unbelievable Sunset View

Matlacha

16% off
S$2,457
for 7 nights, 1 home
S$351 per night
includes taxes & fees
Turtle House - Waterfront with Dock - Unbelievable Sunset View
Marina
Dining
Living area
Pool
Exceptional
(31 reviews)

Island Getaway Florida

Saint James City

11% off
S$3,301
for 7 nights, 1 home
S$472 per night
includes taxes & fees
Island Getaway Florida
Dining
Interior
Exterior detail
Exterior detail
Exceptional
(61 reviews)

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

Bokeelia

8% off
S$810
for 7 nights, 1 cottage
S$116 per night
includes taxes & fees
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
Pool
Marina
Private kitchen
Living area
Exceptional
(8 reviews)

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

Saint James City

7% off
S$3,769
for 7 nights, 1 home
S$538 per night
includes taxes & fees
3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat
Living & Dining
Location
Master bedroom
Kitchen
Exceptional
(32 reviews)

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

Saint James City

8% off
S$4,170
for 7 nights, 1 home
S$596 per night
includes taxes & fees
PERFECT FAMILY GETAWAY - 3 Bedroom / 2 ½ Bath w/ 60' Boat Dock & Private Pool
Queen/master bedroom with bathroom ensuite
Kitchen view from living room
Living area
Terrace/patio
Exceptional
(13 reviews)

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

Saint James City

8% off
S$1,906
for 7 nights, 1 home
S$272 per night
includes taxes & fees
LOCATION Cozy bungalow on Monroe Canal, the most entertaining / traveled canal
Welcome to Paradise
Welcome to Island Club North Captiva, where every moment is a chapter in your own island story. Dive into relaxation, adventure, and the unparalleled charm of this coastal paradise. Your island escape awaits.
“The calm before the plane lands—just us, the breeze, and a beautiful view 🌞👶✈️”
Aerial view
Exceptional
(12 reviews)

Car-Free Island Escape | Pool, Spa + Golf Cart

Captiva

7% off
S$6,878
for 7 nights, 1 home
S$983 per night
includes taxes & fees
Car-Free Island Escape | Pool, Spa + Golf Cart
Dolphins' fountain in front yard.
Magnificent sunset views from screened porch overlooking pool and golf course.
Breakfast in screened porch overlooking pool, backyard and  lakes and greens.
Backyard fountain. The soothing sound of falling waters fills pool deck & yard.
Exceptional
(112 reviews)

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

Sanibel

8% off
S$7,055
for 7 nights, 1 home
S$1,008 per night
includes taxes & fees
SANIBEL SUN CASTLE Splendid home, heated pool, great location, bike to beach.
Living area
Living area
Living area
Living area
Exceptional
(65 reviews)

⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️

Captiva

15% off
S$5,211
for 7 nights, 1 apartment
S$744 per night
includes taxes & fees
⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️
Room
Living area
Living area
Exterior
Excellent
(15 reviews)

Waterfront House Best Location! Private deep water dock

Captiva

8% off
S$8,281
for 7 nights, 1 home
S$1,183 per night
includes taxes & fees
Waterfront House Best Location! Private deep water dock
Dining
Living area
Living area
Dining
Exceptional
(46 reviews)

⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️

Captiva

15% off
S$4,948
for 7 nights, 1 apartment
S$707 per night
includes taxes & fees
⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️
Interior
Living area
Living area
Pool
Exceptional
(111 reviews)

Sundial F401 Penthouse Beachfront with Wrap Around Balcony

Sanibel

8% off
S$3,742
for 7 nights, 1 apartment
S$535 per night
includes taxes & fees
Sundial F401 Penthouse Beachfront with Wrap Around Balcony
Enjoy a cup of coffee or a glass of wine listening to the waves.
Enjoy a cup of coffee or a glass of wine.
View from Lanai
Peaceful evening on a large lanai.  View is more expansive since Ian.
Exceptional
(101 reviews)

Sundial of Sanibel B307, Direct Beachview

Sanibel

8% off
S$3,081
for 7 nights, 1 apartment
S$440 per night
includes taxes & fees
Sundial of Sanibel B307, Direct Beachview
Living area
Living area
Exterior
Property grounds
Excellent
(24 reviews)

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

Captiva

8% off
S$3,974
for 7 nights, 1 cottage
S$568 per night
includes taxes & fees
Spacious "Crab Cakes" Cottage on N. Captiva with GolfCart, Starlink and new AC
Interior
Living area
Dining
Room
Exceptional
(16 reviews)

Beachfront Condo, 2bd/2bath Pet-Friendly

Sanibel

8% off
S$3,381
for 7 nights, 1 apartment
S$483 per night
includes taxes & fees
Beachfront Condo, 2bd/2bath Pet-Friendly
2nd level condo (middle of photo) with private, patio and trooical garden view.
Private access path to Sanibel’s famous Gulf of Mexico beach.
Just steps to the beach or our pool as you relax in this tropical setting.
Living room - all the comforts of home.  Cable TV, Wi-Fi.
Exceptional
(50 reviews)

Tropical Garden Condo Just Steps to Sanibel Beach

Sanibel

8% off
S$4,254
for 7 nights, 1 apartment
S$608 per night
includes taxes & fees
Tropical Garden Condo Just Steps to Sanibel Beach
Exterior
Beach
Living area
Dining
Exceptional
(128 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!
  • 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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