Pine Island holiday homes

We found 10,893 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Pine Island

Showing deals for:29 Jan - 5 Feb

Exterior
Exceptional
(204 reviews)

Historic 1911 Cottage with Pool, 2 Blocks from Orange Sunsets on Beach and Town

Boca Grande

8% off
NZ$19,841
for 7 nights, 1 home
NZ$2,834 per night
includes taxes & fees
Historic 1911 Cottage with Pool, 2 Blocks from Orange Sunsets on Beach and Town
Living area
Exceptional
(18 reviews)

🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!

Fort Myers Beach

7% off
NZ$2,883
for 7 nights, 1 apartment
NZ$412 per night
includes taxes & fees
🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!
Magnificent sunset views from screened porch overlooking pool and golf course.
Exceptional
(113 reviews)

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

Sanibel

8% off
NZ$9,126
for 7 nights, 1 home
NZ$1,304 per night
includes taxes & fees
SANIBEL SUN CASTLE Splendid home, heated pool, great location, bike to beach.
Exterior
Exceptional
(6 reviews)

Walk To Beach, North End Restaurants, Night Life Steps Away!

Fort Myers Beach

7% off
NZ$3,552
for 7 nights, 1 apartment
NZ$507 per night
includes taxes & fees
Walk To Beach, North End Restaurants, Night Life Steps Away!
Exterior
Exceptional
(108 reviews)

Sun Soaked Coastal Getaway, Private Heated Pool, Steps to Sugar Sand Beach!

Fort Myers Beach

7% off
NZ$7,667
for 7 nights, 1 home
NZ$1,095 per night
includes taxes & fees
Sun Soaked Coastal Getaway, Private Heated Pool, Steps to Sugar Sand Beach!
Aerial view
Exceptional
(12 reviews)

North Captiva Island Retreat w/ Pool & Cart

Captiva

7% off
NZ$12,700
for 7 nights, 1 home
NZ$1,814 per night
includes taxes & fees
North Captiva Island Retreat w/ Pool & Cart
Private kitchen
Exceptional
(13 reviews)

Sleeps 16--New Pool!--7 min walk to beach, Bay views!

Fort Myers Beach

8% off
NZ$16,601
for 7 nights, 1 home
NZ$2,372 per night
includes taxes & fees
Sleeps 16--New Pool!--7 min walk to beach, Bay views!
Private kitchen
Exceptional
(18 reviews)

Luxury Home - 4BR - Private Outdoor Oasis w/ Htd Saltwater Pool - Game Rm w/ PS5

Cape Coral

16% off
NZ$7,585
for 7 nights, 1 home
NZ$1,084 per night
includes taxes & fees
Luxury Home - 4BR - Private Outdoor Oasis w/ Htd Saltwater Pool - Game Rm w/ PS5
Interior
Excellent
(12 reviews)

🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!

Fort Myers Beach

7% off
NZ$2,936
for 7 nights, 1 apartment
NZ$419 per night
includes taxes & fees
🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!
infinity pool with view of canal / palm trees.
Exceptional
(20 reviews)

Huge 3,263 sq ft Family Getaway: Kid-Friendly Upstairs Den!

Cape Coral

7% off
NZ$7,244
for 7 nights, 1 home
NZ$1,035 per night
includes taxes & fees
Huge 3,263 sq ft Family Getaway: Kid-Friendly Upstairs Den!
Pool
Wonderful
(23 reviews)

Fenced Yard & Pool · BBQ & Kayaks

Cape Coral

28% off
NZ$7,287
for 7 nights, 1 villa
NZ$1,041 per night
includes taxes & fees
Fenced Yard & Pool · BBQ & Kayaks
Private kitchen
Exceptional
(40 reviews)

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

Cape Coral

8% off
NZ$8,416
for 7 nights, 1 home
NZ$1,202 per night
includes taxes & fees
Coconut Cove Home with Sunny South-Facing Family Pool, Canal & Boat Dock
1,400 sq ft of outdoor living: screened lanai, full outdoor kitchen with grill and refrigerator, and lounge space for sunset gatherings.
Exceptional
(24 reviews)

Pet-Friendly North Captiva Home | Pool & Cart

Captiva

7% off
NZ$13,533
for 7 nights, 1 home
NZ$1,933 per night
includes taxes & fees
Pet-Friendly North Captiva Home | Pool & Cart
Interior
Exceptional
(15 reviews)

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

Matlacha

6% off
NZ$4,888
for 7 nights, 1 home
NZ$698 per night
includes taxes & fees
New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS
Pool
Exceptional
(37 reviews)

NEW Aqua Vista-SW Cape Coral Gulf Access Pool Home

Cape Coral

8% off
NZ$5,366
for 7 nights, 1 home
NZ$767 per night
includes taxes & fees
NEW Aqua Vista-SW Cape Coral Gulf Access Pool Home
Dining
Exceptional
(19 reviews)

Cozy Beach Villa, Shared Heated Pool, Steps to Beach, Restaurants!

Fort Myers Beach

7% off
NZ$5,575
for 7 nights, 1 apartment
NZ$796 per night
includes taxes & fees
Cozy Beach Villa, Shared Heated Pool, Steps to Beach, Restaurants!
Living area
Excellent
(9 reviews)

Spacious 5-bedroom Cape Coral house with a pool and amenities just like home!

Cape Coral

7% off
NZ$5,092
for 7 nights, 1 home
NZ$727 per night
includes taxes & fees
Spacious 5-bedroom Cape Coral house with a pool and amenities just like home!
Room
Wonderful
(48 reviews)

Chic Cape Coral Studio – Near Yacht Club, Kitchen + Laundry

Cape Coral

7% off
NZ$1,823
for 7 nights, 1 apartment
NZ$260 per night
includes taxes & fees
Chic Cape Coral Studio – Near Yacht Club, Kitchen + Laundry
Terrace/patio
Very good
(62 reviews)

Spacious Beach Retreat, Steps to Sugary Sand, Conveniences and Fun!

Fort Myers Beach

7% off
NZ$3,463
for 7 nights, 1 apartment
NZ$495 per night
includes taxes & fees
Spacious Beach Retreat, Steps to Sugary Sand, Conveniences and Fun!
Oversized Salt water pool with spa
Pool 80+ degrees
Spa 100+ degrees, on demand
Exceptional
(48 reviews)

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

Bokeelia

6% off
NZ$3,645
for 7 nights, 1 home
NZ$521 per night
includes taxes & fees
Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife
Interior
Exceptional
(72 reviews)

Beach front with 2 bedrooms, 2 baths and views of the Gulf!

Fort Myers Beach

8% off
NZ$4,368
for 7 nights, 1 apartment
NZ$624 per night
includes taxes & fees
Beach front with 2 bedrooms, 2 baths and views of the Gulf!
Games on "Beachy" Backard
Exceptional
(54 reviews)

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

Captiva

8% off
NZ$11,233
for 7 nights, 1 home
NZ$1,605 per night
includes taxes & fees
Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week
Exterior
Exceptional
(129 reviews)

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

Captiva

8% off
NZ$6,652
for 7 nights, 1 apartment
NZ$950 per night
includes taxes & fees
Stunning Modern beach front unit - completely renovated! Includes golf cart!
Community pool
Excellent
(21 reviews)

Fantastic Island Getaway at Sunset Captiva 48

Captiva

8% off
NZ$9,722
for 7 nights, 1 home
NZ$1,389 per night
includes taxes & fees
Fantastic Island Getaway at Sunset Captiva 48
  • 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)
  • Fort Myers Country Club (14.4 mi / 23.1 km)
  • Cape Royal Golf Club (5.3 mi / 8.5 km)
  • Palmetto-Pine Country Club (7.3 mi / 11.7 km)
  • Coral Oaks Golf Course (7.9 mi / 12.8 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.

More holiday ideas