Pine Island holiday rentals

We found 10,818 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Pine Island

Showing deals for:4 Dec - 11 Dec

Property grounds
Room
Interior
Private kitchen
Exceptional
(60 reviews)

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

Matlacha

8% off
AU$1,673
for 7 nights, 1 room
AU$239 per night
includes taxes & fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Living area
Private kitchen
Outdoor dining
Exterior
Exceptional
(17 reviews)

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

Cape Coral

7% off
AU$3,304
for 7 nights, 1 villa
AU$472 per night
includes taxes & fees
Experience Unparalleled Luxury and Serenity at Villa Soulside, Cape Coral, FL
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$1,374
for 7 nights, 1 home
AU$196 per night
includes taxes & fees
Charming duplex in quiet SW Florida, near The Beach, shops, dining, and more!
Stocked kitchen boasts double oven and craft ice in the refrigerator
Breathtaking views with fabulous infinity pool and Thunderbird Lake!
Large island conveniently located between kitchen and living room
Private boat and dock with gas fire table.  Easily get boat into water with lift
Exceptional
(118 reviews)

Waterfront, Infinity Pool, BOAT Included in price, Pool Table/Ping Pong, SUPs

Cape Coral

5% off
AU$4,004
for 7 nights, 1 home
AU$572 per night
includes taxes & fees
Waterfront, Infinity Pool, BOAT Included in price, Pool Table/Ping Pong, SUPs
Exterior
Living area
Dining
Living area
Wonderful
(21 reviews)

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

Fort Myers Beach

7% off
AU$5,374
for 7 nights, 1 home
AU$768 per night
includes taxes & fees
New to Market! 🐾 Dog Friendly, Spacious Beach Retreat, Steps to Sugary Sand, Conveniences!
Property grounds
Private kitchen
Interior
Interior
Exceptional
(10 reviews)

Relaxing 3-Bedroom Matlacha Cottage with Private Pool & Dock

Matlacha

7% off
AU$3,795
for 7 nights, 1 cottage
AU$542 per night
includes taxes & fees
Relaxing 3-Bedroom Matlacha Cottage with Private Pool & Dock
Outdoor dining
Beach
Pool
Living area
Exceptional
(8 reviews)

Florida Style Villa by the Water with heated Pool, Dock, Gulf access! Kayaks!

Matlacha

7% off
AU$2,532
for 7 nights, 1 villa
AU$362 per night
includes taxes & fees
Florida Style Villa by the Water with heated Pool, Dock, Gulf access! Kayaks!
Room
Pool
Interior
Gathering area with great views
Exceptional
(45 reviews)

Ultimate luxury resort style home on Matlacha

Matlacha

8% off
AU$10,821
for 7 nights, 1 home
AU$1,546 per night
includes taxes & fees
Ultimate luxury resort style home on Matlacha
Outdoor dining
Pool
Living area
Property grounds
Exceptional
(29 reviews)

Great Family Vacation, Waterfront Pool Home

Cape Coral

8% off
AU$4,663
for 7 nights, 1 home
AU$666 per night
includes taxes & fees
Great Family Vacation, Waterfront Pool Home
Dining
Outdoor dining
Exterior
Private kitchen
Exceptional
(7 reviews)

Turtle House - Waterfront with Dock - Unbelievable Sunset View

Matlacha

16% off
AU$2,702
for 7 nights, 1 home
AU$386 per night
includes taxes & fees
Turtle House - Waterfront with Dock - Unbelievable Sunset View
Property grounds
Outdoor dining
Exterior
Room
Exceptional
(11 reviews)

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

Matlacha

7% off
AU$1,818
for 7 nights, 1 cottage
AU$260 per night
includes taxes & fees
Orange You Glad Cottage - A Fisherman’s Paradise in sunny Matlacha
Terrace/patio
Private kitchen
Pool
Living area
Exceptional
(19 reviews)

Paradise of Cape Coral on Canal, with Heated Pool, Tiki Hut Grill & Elec Bikes

Cape Coral

6% off
AU$2,122
for 7 nights, 1 home
AU$303 per night
includes taxes & fees
Paradise of Cape Coral on Canal, with Heated Pool, Tiki Hut Grill & Elec Bikes
Private kitchen
Interior
Interior
Living area
Exceptional
(15 reviews)

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

Matlacha

6% off
AU$3,190
for 7 nights, 1 home
AU$456 per night
includes taxes & fees
New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS
Marina
Dining
Exterior
Pool
Exceptional
(31 reviews)

Island Getaway Florida

Saint James City

11% off
AU$3,545
for 7 nights, 1 home
AU$506 per night
includes taxes & fees
Island Getaway Florida
Private kitchen
Exterior
Living area
Beach
Exceptional
(37 reviews)

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

Fort Myers Beach

7% off
AU$5,228
for 7 nights, 1 home
AU$747 per night
includes taxes & fees
Charming Home, Private Pool, Short Walk to Restaurants and Beach!
Outdoor dining
Private kitchen
Property grounds
Exterior
Excellent
(6 reviews)

Cozy home quiet area, short drive to the beach. Perfect for traveling nurse

Cape Coral

6% off
AU$1,091
for 7 nights, 1 home
AU$156 per night
includes taxes & fees
Cozy home quiet area, short drive to the beach. Perfect for traveling nurse
Exterior detail
Interior
Room
Dining
Exceptional
(61 reviews)

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

Bokeelia

8% off
AU$885
for 7 nights, 1 cottage
AU$126 per night
includes taxes & fees
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
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.
“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
AU$7,530
for 7 nights, 1 home
AU$1,076 per night
includes taxes & fees
Car-Free Island Escape | Pool, Spa + Golf Cart
Exterior
Terrace/patio
Living area
Pool
Exceptional
(77 reviews)

Top Location w/direct gulf access. Newly renovated kitchen and bathrooms

Cape Coral

7% off
AU$2,864
for 7 nights, 1 home
AU$409 per night
includes taxes & fees
Top Location w/direct gulf access. Newly renovated kitchen and bathrooms
Top deck lanai
Location
Living & Dining
Master bedroom
Exceptional
(32 reviews)

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

Saint James City

8% off
AU$4,463
for 7 nights, 1 home
AU$638 per night
includes taxes & fees
PERFECT FAMILY GETAWAY - 3 Bedroom / 2 ½ Bath w/ 60' Boat Dock & Private Pool
Living area
Kitchen view from living room
Terrace/patio
Property grounds
Exceptional
(13 reviews)

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

Saint James City

8% off
AU$2,114
for 7 nights, 1 home
AU$302 per night
includes taxes & fees
LOCATION Cozy bungalow on Monroe Canal, the most entertaining / traveled canal
Interior
Outdoor dining
Enjoy relaxing on quiet back porch. table for 6 spacious back yard mango orchard
Room
Exceptional
(27 reviews)

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

Bokeelia

15% off
AU$1,571
for 7 nights, 1 home
AU$224 per night
includes taxes & fees
Are you looking for old Florida.? Lower heart rate? No high rises/ traffic?
Private kitchen
Marina
Room
Living area
Exceptional
(8 reviews)

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

Saint James City

8% off
AU$4,036
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat
Private kitchen
Property grounds
Room
Interior
Exceptional
(61 reviews)

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

Fort Myers Beach

7% off
AU$2,608
for 7 nights, 1 apartment
AU$373 per night
includes taxes & fees
Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet
  • 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 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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