Pine Island holiday homes

We found 10,810 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Pine Island

Showing deals for:11 Dec - 18 Dec

Private kitchen
Room
Interior
Outdoor dining
Exceptional
(60 reviews)

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

Matlacha

8% off
NZ$2,074
for 7 nights, 1 room
NZ$296 per night
includes taxes & fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Exterior
Private kitchen
Outdoor dining
Living area
Exceptional
(18 reviews)

Experience Unparalleled Luxury and Serenity at Villa Soulside, Cape Coral, FL

Cape Coral

7% off
NZ$4,097
for 7 nights, 1 villa
NZ$585 per night
includes taxes & fees
Experience Unparalleled Luxury and Serenity at Villa Soulside, Cape Coral, FL
Room
Exterior
Dining
Private kitchen
Exceptional
(30 reviews)

Charming duplex in quiet SW Florida, near The Beach, shops, dining, and more!

Cape Coral

8% off
NZ$1,720
for 7 nights, 1 home
NZ$246 per night
includes taxes & fees
Charming duplex in quiet SW Florida, near The Beach, shops, dining, and more!
Interior
Private kitchen
Property grounds
Interior
Exceptional
(10 reviews)

Relaxing 3-Bedroom Matlacha Cottage with Private Pool & Dock

Matlacha

8% off
NZ$5,760
for 7 nights, 1 cottage
NZ$823 per night
includes taxes & fees
Relaxing 3-Bedroom Matlacha Cottage with Private Pool & Dock
Dining
Living area
Private kitchen
Exterior
Wonderful
(21 reviews)

New to Market! 🐾 Dog Friendly, Spacious Beach Retreat, Steps to Sugary Sand, Conveniences!

Fort Myers Beach

7% off
NZ$6,589
for 7 nights, 1 home
NZ$941 per night
includes taxes & fees
New to Market! 🐾 Dog Friendly, Spacious Beach Retreat, Steps to Sugary Sand, Conveniences!
Pool
Beautiful canal to enjoy fishing, kayaking or just relaxing
Kitchen island
Interior
Exceptional
(42 reviews)

Waterfront Escape- Spacious 4 Bedroom Canal Home minutes to Ft Myers Beach

Cape Coral

7% off
NZ$3,144
for 7 nights, 1 home
NZ$449 per night
includes taxes & fees
Waterfront Escape- Spacious 4 Bedroom Canal Home minutes to Ft Myers Beach
Dining
Private kitchen
Living area
Pool
Exceptional
(37 reviews)

Coconut Cove Home with Sunny South-Facing Family Pool, Canal & Boat Dock

Cape Coral

7% off
NZ$4,957
for 7 nights, 1 home
NZ$708 per night
includes taxes & fees
Coconut Cove Home with Sunny South-Facing Family Pool, Canal & Boat Dock
Living area
Dining
Room
Living area
Exceptional
(34 reviews)

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

Captiva

8% off
NZ$6,250
for 7 nights, 1 home
NZ$893 per night
includes taxes & fees
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
Property grounds
Pool
Outdoor dining
Living area
Exceptional
(29 reviews)

Great Family Vacation, Waterfront Pool Home

Cape Coral

8% off
NZ$5,875
for 7 nights, 1 home
NZ$839 per night
includes taxes & fees
Great Family Vacation, Waterfront Pool Home
Living area
Interior
Living area
Private kitchen
Exceptional
(15 reviews)

New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS

Matlacha

6% off
NZ$4,416
for 7 nights, 1 home
NZ$631 per night
includes taxes & fees
New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS
Exterior
Outdoor dining
Private kitchen
Dining
Exceptional
(7 reviews)

Turtle House - Waterfront with Dock - Unbelievable Sunset View

Matlacha

16% off
NZ$3,346
for 7 nights, 1 home
NZ$478 per night
includes taxes & fees
Turtle House - Waterfront with Dock - Unbelievable Sunset View
Exterior
Outdoor dining
Room
Property grounds
Exceptional
(11 reviews)

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

Matlacha

7% off
NZ$2,251
for 7 nights, 1 cottage
NZ$322 per night
includes taxes & fees
Orange You Glad Cottage - A Fisherman’s Paradise in sunny Matlacha
Outdoor dining
Exterior
Living area
Private kitchen
Exceptional
(38 reviews)

Charming Home, Private Pool, Short Walk to Restaurants and Beach!

Fort Myers Beach

7% off
NZ$7,026
for 7 nights, 1 home
NZ$1,004 per night
includes taxes & fees
Charming Home, Private Pool, Short Walk to Restaurants and Beach!
Exterior
Dining
Pool
Living area
Exceptional
(31 reviews)

Island Getaway Florida

Saint James City

11% off
NZ$4,466
for 7 nights, 1 home
NZ$638 per night
includes taxes & fees
Island Getaway Florida
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 🌞👶✈️”
Spacious, inviting, and ready to welcome all. Our home offers room for everyone, ensuring that every gathering is filled with laughter, warmth, and shared moments. Create memories that resonate in every corner
Exceptional
(12 reviews)

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

Captiva

7% off
NZ$9,307
for 7 nights, 1 home
NZ$1,330 per night
includes taxes & fees
Car-Free Island Escape | Pool, Spa + Golf Cart
Exterior
Pool
Living area
Private kitchen
Exceptional
(22 reviews)

Beautiful, SOUTHERN EXPOSURE home with a pool

Cape Coral

7% off
NZ$3,150
for 7 nights, 1 home
NZ$450 per night
includes taxes & fees
Beautiful, SOUTHERN EXPOSURE home with a pool
Living & Dining
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
NZ$5,628
for 7 nights, 1 home
NZ$804 per night
includes taxes & fees
PERFECT FAMILY GETAWAY - 3 Bedroom / 2 ½ Bath w/ 60' Boat Dock & Private Pool
Private kitchen
Marina
Pool
Room
Exceptional
(8 reviews)

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

Saint James City

7% off
NZ$5,101
for 7 nights, 1 home
NZ$729 per night
includes taxes & fees
3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat
Room
Interior
Dining
Exterior detail
Exceptional
(61 reviews)

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

Bokeelia

8% off
NZ$1,096
for 7 nights, 1 cottage
NZ$157 per night
includes taxes & fees
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
Breakfast in screened porch overlooking pool, backyard and  lakes and greens.
Magnificent sunset views from screened porch overlooking pool and golf course.
Backyard fountain. The soothing sound of falling waters fills pool deck & yard.
Dolphins' fountain in front yard.
Exceptional
(112 reviews)

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

Sanibel

8% off
NZ$9,599
for 7 nights, 1 home
NZ$1,371 per night
includes taxes & fees
SANIBEL SUN CASTLE Splendid home, heated pool, great location, bike to beach.
Room
Outdoor dining
Interior
Dining
Exceptional
(27 reviews)

Are you looking for old Florida.? Lower heart rate? No high rises/ traffic?

Bokeelia

15% off
NZ$1,946
for 7 nights, 1 home
NZ$278 per night
includes taxes & fees
Are you looking for old Florida.? Lower heart rate? No high rises/ traffic?
Dining
Exterior
Pool
Private kitchen
Exceptional
(17 reviews)

LOCATION!! LOCATION!! SHORT WALKING TO RESTAURANTS, SHOPS, & BEACH!

Fort Myers Beach

7% off
NZ$3,459
for 7 nights, 1 home
NZ$494 per night
includes taxes & fees
LOCATION!! LOCATION!! SHORT WALKING TO RESTAURANTS, SHOPS, & BEACH!
Exterior
Living area
Living area
Private kitchen
Exceptional
(20 reviews)

Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 6.

Fort Myers Beach

7% off
NZ$5,648
for 7 nights, 1 home
NZ$807 per night
includes taxes & fees
Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 6.
Living area
Living area
Room
Pool
Excellent
(15 reviews)

Waterfront House Best Location! Private deep water dock

Captiva

8% off
NZ$11,301
for 7 nights, 1 home
NZ$1,614 per night
includes taxes & fees
Waterfront House Best Location! Private deep water dock
  • 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

Explore the waterfront setting in Pine Island

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Pine Island. This relaxing city is known for its fishing, boating and cycling. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Pine Island

Are you hoping to discover top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Pine Island has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Sun Splash Water Park (8.8 mi / 14.2 km)
  • Sanibel Island Golf Club (11.6 mi / 18.7 km)
  • Palmetto-Pine Country Club (7.3 mi / 11.7 km)
  • Coral Oaks Golf Course (7.9 mi / 12.8 km)
  • Mike Greenwell's Bat-A-Ball & Family Fun Park (9.6 mi / 15.5 km)
  • Dunes Golf and Tennis Club (10.6 mi / 17.1 km)

Exploring the natural features in Pine Island

Whether you're an adventurous traveller or just want to take in the scenery, Pine Island is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • North Captiva Island Beach (6.3 mi / 10.2 km)
  • Useppa Island (7.8 mi / 12.5 km)
  • Captiva Beach (7.9 mi / 12.8 km)
  • Cabbage Key (8.1 mi / 13.1 km)
  • Cayo Costa Beaches (8.3 mi / 13.4 km)
  • Turner Beach (9 mi / 14.5 km)

Frequently asked questions

What is the best area to stay in Pine Island when booking a holiday home?
One of the more sought-after areas for a Pine Island holiday home is Saint James City. When you book a holiday home with Bookabach, you'll enjoy having the whole place to yourself. This means you don't have to share it with anybody apart from your people.
What is the most popular type of holiday home accommodation in Pine Island?
The most in-demand types of holiday homes in Pine Island are houses. Hoping for something different? Bookabach has many options to match the unique needs of our guests, so you'll see properties in loads of sizes and shapes. The perfect fit is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Pine Island?
Length of stay, property type and time of year are some things that can affect the price of a holiday home. Simply enter your travel dates to find your perfect match. From cosy chalets to expansive villas, all Bookabach holiday homes provide amazing value.
How much does it cost to rent a beach house in Pine Island?
When you travel and the style and size of the property will influence the cost of your beachside escape. Enter your Pine Island travel dates to see all your options on Bookabach. Can't live without a private pool? Use our filters to pick the features and amenities you need.
What are popular home amenities in Pine Island?
Some of the most popular home amenities people are searching for in Pine Island include a microwave oven, a dryer and a fridge. Whether you're travelling with your besties, family or even pets, Bookabach holiday properties feature the best amenities for hanging out with the people you cherish the most.
Are there large group holiday homes in Pine Island?
There are nine holiday homes in Pine Island that can accommodate a group of 10 or more guests. Whether you're organising a holiday with extended family or an event like a birthday party, there's ample space to get your loved ones together under the same roof.
Can I find two-bedroom holiday homes in Pine Island?
Take off with your loved ones and enjoy peace, privacy and comfort in one of the 103 two-bedroom holiday homes Pine Island has to offer.
Are there holiday homes with WiFi in Pine Island?
Take your pick of 90 holiday homes with WiFi in Pine Island. If you want to disconnect from daily life on your escape, but still need to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Bookabach.
How old do you have to be to rent a holiday home in Pine Island?
The minimum age is generally 16, 18 or 21. It can vary between properties on Bookabach, so check the rules of your preferred Pine Island holiday home before you book.
How long can I rent a holiday home in Pine Island for?
How long you can book a holiday home in Pine Island depends on the property. Simply enter your desired travel dates to look at a list of options offering extended stays. With loads of features such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to discover someplace just right to call your home away from home in Pine Island.

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