Pine Island holiday rentals

We found 10,823 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Pine Island

Showing deals for:1 Jan - 8 Jan

Room
Living area
Exterior
Terrace/patio
Exceptional
(18 reviews)

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

Fort Myers Beach

7% off
AU$2,729
for 7 nights, 1 apartment
AU$390 per night
includes taxes & fees
🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!
Exterior: Vibrant coastal charm awaits! Enjoy island living with tropical views & spacious balconies.
Exterior: Stunning island escape with panoramic views and a sun-kissed rooftop deck!
Outdoor Paradise: Dive into relaxation by the sparkling pool with ample lounging space!
Beachfront Paradise: Swaying palms and stunning sea views just steps from your door!
Exceptional
(128 reviews)

Panoramic Gulf Views | Heated Pool | Beach

Captiva

12% off
AU$8,733
for 7 nights, 1 home
AU$1,248 per night
includes taxes & fees
Panoramic Gulf Views | Heated Pool | Beach
Private kitchen
Pool
Exterior
Living area
Exceptional
(11 reviews)

🌴🥥🍹Entire Luxury Duplex With Gulf Access Canal View Saltwater Pool🌴🥥🍹

Cape Coral

8% off
AU$10,342
for 7 nights, 1 home
AU$1,477 per night
includes taxes & fees
🌴🥥🍹Entire Luxury Duplex With Gulf Access Canal View Saltwater Pool🌴🥥🍹
Exterior
Room
Bathroom
Private kitchen
Wonderful
(47 reviews)

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

Cape Coral

8% off
AU$1,457
for 7 nights, 1 apartment
AU$208 per night
includes taxes & fees
Chic Cape Coral Studio – Near Yacht Club, Kitchen + Laundry
Dining
Exterior
Private kitchen
Interior
Exceptional
(30 reviews)

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

Cape Coral

8% off
AU$1,425
for 7 nights, 1 home
AU$204 per night
includes taxes & fees
Charming duplex in quiet SW Florida, near The Beach, shops, dining, and more!
Marina
Exterior
Pool & Spa on Waterfront Property
Terrace/patio
Exceptional
(41 reviews)

VILLA COCONUT - Waterfront w/ Gulf Access Vacation Rental

Cape Coral

8% off
AU$4,297
for 7 nights, 1 home
AU$614 per night
includes taxes & fees
VILLA COCONUT - Waterfront w/ Gulf Access Vacation Rental
Private kitchen
Beach
Interior
Living area
Exceptional
(38 reviews)

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

Captiva

8% off
AU$5,772
for 7 nights, 1 home
AU$825 per night
includes taxes & fees
Spectacular beach front views with a short walk to members only beach
Pool
Private kitchen
Property grounds
Interior
Exceptional
(10 reviews)

Relaxing 3-Bedroom Matlacha Cottage with Private Pool & Dock

Matlacha

8% off
AU$4,730
for 7 nights, 1 cottage
AU$676 per night
includes taxes & fees
Relaxing 3-Bedroom Matlacha Cottage with Private Pool & Dock
Dining for 6 with gorgeous window to pool.  Extra banquet table for 10 available
infinity pool with view of canal / palm trees.
Open floor plan, tasteful furniture in living room!
Spacious upstairs with kids sleeping area, and bean bag chairs!
Exceptional
(20 reviews)

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

Cape Coral

8% off
AU$6,042
for 7 nights, 1 home
AU$863 per night
includes taxes & fees
Huge 3,263 sq ft Family Getaway: Kid-Friendly Upstairs Den!
Interior
Property grounds
Room
Private kitchen
Exceptional
(61 reviews)

Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet

Fort Myers Beach

8% off
AU$3,636
for 7 nights, 1 apartment
AU$519 per night
includes taxes & fees
Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet
Aerial view
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.
Welcome to Paradise
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

8% off
AU$12,373
for 7 nights, 1 home
AU$1,768 per night
includes taxes & fees
Car-Free Island Escape | Pool, Spa + Golf Cart
Property grounds
Private kitchen
Living area
Living area
Excellent
(9 reviews)

Casa Lakehouse 3BD 3BH Heated Pool Lake View

Fort Myers

7% off
AU$2,969
for 7 nights, 1 home
AU$424 per night
includes taxes & fees
Casa Lakehouse 3BD 3BH Heated Pool Lake View
Living area
Marina
Room
Private kitchen
Exceptional
(8 reviews)

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

Saint James City

7% off
AU$4,384
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat
Exterior
Dining
Living area
Pool
Exceptional
(31 reviews)

Island Getaway Florida

Saint James City

11% off
AU$3,669
for 7 nights, 1 home
AU$524 per night
includes taxes & fees
Island Getaway Florida
Living area
Interior
Living area
Interior
Exceptional
(15 reviews)

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

Matlacha

6% off
AU$4,005
for 7 nights, 1 home
AU$572 per night
includes taxes & fees
New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS
Room
Dining
Interior
Exterior
Exceptional
(24 reviews)

9th place Coastal Oasis

Cape Coral

7% off
AU$2,139
for 7 nights, 1 home
AU$306 per night
includes taxes & fees
9th place Coastal Oasis
Master bedroom
Location
Kitchen
Living & Dining
Exceptional
(32 reviews)

Escape to Paradise – 3 Bedrooms, 2½ Baths, Private Pool & 60' Boat Dock

Saint James City

8% off
AU$4,621
for 7 nights, 1 home
AU$660 per night
includes taxes & fees
Escape to Paradise – 3 Bedrooms, 2½ Baths, Private Pool & 60' Boat Dock
Private kitchen
Terrace/patio
Exterior
Living area
Exceptional
(11 reviews)

NEWLY REMODELED-Peaceful Florida Island Home-5 minute canal ride to Gulf waters!

Saint James City

8% off
AU$2,638
for 7 nights, 1 home
AU$377 per night
includes taxes & fees
NEWLY REMODELED-Peaceful Florida Island Home-5 minute canal ride to Gulf waters!
Living area
Living area
Living area
Living area
Exceptional
(65 reviews)

⚓️South Seas Serenity Coastal Luxury Beach Condo⚓️

Captiva

16% off
AU$6,691
for 7 nights, 1 apartment
AU$956 per night
includes taxes & fees
⚓️South Seas Serenity 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.
Breakfast in screened porch overlooking pool, backyard and  lakes and greens.
Exceptional
(112 reviews)

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

Sanibel

8% off
AU$9,291
for 7 nights, 1 home
AU$1,327 per night
includes taxes & fees
SANIBEL SUN CASTLE Splendid home, heated pool, great location, bike to beach.
Dining
Living area
Living area
Dining
Exceptional
(46 reviews)

⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️

Captiva

16% off
AU$6,568
for 7 nights, 1 apartment
AU$938 per night
includes taxes & fees
⚓️South Seas Serenity II Coastal Luxury Beach Condo⚓️
Private kitchen
Living area
Room
Living area
Exceptional
(20 reviews)

Cape Coral Nature Retreat with Adjacent Boating, Fishing & Trails

Cape Coral

8% off
AU$2,965
for 7 nights, 1 home
AU$424 per night
includes taxes & fees
Cape Coral Nature Retreat with Adjacent Boating, Fishing & Trails
Interior
Living area
Living area
Dining
Exceptional
(7 reviews)

Penthouse Suite 2 in the heart of SW Cape Coral

Cape Coral

7% off
AU$2,028
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
Penthouse Suite 2 in the heart of SW Cape Coral
Pool
Interior
Living area
Dining
Exceptional
(14 reviews)

Pink Pineapple ~ Walk to Downtown ~ Chic Heated Pool Home

Cape Coral

8% off
AU$3,788
for 7 nights, 1 home
AU$541 per night
includes taxes & fees
Pink Pineapple ~ Walk to Downtown ~ Chic Heated Pool Home
  • 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)
  • 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)
  • Mike Greenwell's Bat-A-Ball & Family Fun Park (9.6 mi / 15.5 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 Stayz, 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? Stayz 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 Stayz 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 Stayz. 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, Stayz 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 Stayz.
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 Stayz, 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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