Top 50 Pine Island Vacation Rentals

Houses (2,773)
Condos (2,756)
Villas (814)
Golf rental (4,273)
Beachfront (3,120)
Beach view (1,338)

Explore a selection of Pine Island vacation rentals

Enjoy Island Comfort
Guests6
Bedrooms2
Bathroom1
Wonderful 4.4 / 5
$46 avg/night
2 beds
1 Bathroom
Guests 6
5 reviews
4 BR home for bird-watchers, nature lovers, boaters, in St Jame...
Guests6
Bedrooms4
Bathrooms2
Wonderful 0 / 5
$130 avg/night
4 beds
2 Bathrooms
Guests 6
Pet friendly well located updated home with dock/lift on 8th Ave...
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$84 avg/night
2 beds
2 Bathrooms
Guests 5
8 reviews
Enjoy Old Florida Island Life in St James City, FL-Sit and Watch...
Guests6
Bedrooms2
Bathrooms3
Wonderful 4.8 / 5
$200 avg/night
2 beds
3 Bathrooms
Guests 6
5 reviews
NEW! Pine Island Vacation Pool Home on Canal w Dock - Natural...
Guests6
Bedrooms3
Bathroom1
Wonderful 0 / 5
$188 avg/night
3 beds
1 Bathroom
Guests 6
Cozy Villa in the heart of Pine Island/Bokeelia.
Guests3
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$45 avg/night
1 bed
1 Bathroom
Guests 3
5 reviews
Paradise Home with Private Pool & Boat Lift!
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$184 avg/night
2 beds
2 Bathrooms
Guests 6
18 reviews
Available - Stunning location, Private Pool - Great Reviews
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$149 avg/night
3 beds
2 Bathrooms
Guests 6
44 reviews
Peaceful Pine Island Captains Harbor Condo Located in South West...
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$69 avg/night
2 beds
2 Bathrooms
Guests 6
1 reviews
Waterfront home with pool moments away from open water
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.6 / 5
$161 avg/night
3 beds
2 Bathrooms
Guests 8
5 reviews
Quaint Canal Home With Dock & Lift
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$71 avg/night
2 beds
1 Bathroom
Guests 4
7 reviews
Summer/Fall Special *$99* Private Pool - Beautiful Home
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$116 avg/night
2 beds
2 Bathrooms
Guests 4
4 reviews
Perfect Quiet Location with Pool, Bring your boat and golf clubs...
Guests6
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$92 avg/night
3 beds
2 Bathrooms
Guests 6
Cutest Cottage Home in Matlacha
Guests3
Bedrooms2
Bathroom1
Wonderful 4.7 / 5
$86 avg/night
2 beds
1 Bathroom
Guests 3
17 reviews
Welcome! Come stay and play, book now for great rates! Beautiful...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.2 / 5
$107 avg/night
3 beds
2 Bathrooms
Guests 6
5 reviews
Birdwatchers Paradise
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$63 avg/night
2 beds
2 Bathrooms
Guests 4
2 reviews
Immaculate Economy - Pine Island Warmth
Guests3
Bedroom1
Bathroom1
Wonderful 0 / 5
$35 avg/night
1 bed
1 Bathroom
Guests 3
Quaint 2 Bedroom 2.5 Bathroom Condo On Beautiful Pine Island...
Guests6
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$60 avg/night
2 beds
2 Bathrooms
Guests 6
**CALL FOR ACCURATE QUOTE!** 'Casa High Tide' Relax on Quiet...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$142 avg/night
3 beds
2 Bathrooms
Guests 8
16 reviews
JANUARY 2018 NOW OPEN!
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$180 avg/night
2 beds
2 Bathrooms
Guests 5
6 reviews
* St James City * Waterfront * Completely Remodeled 2016 *
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$148 avg/night
2 beds
2 Bathrooms
Guests 6
9 reviews
Bay-front Home With Spectacular Pool On One Of Florida's Best...
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.7 / 5
$344 avg/night
3 beds
3 Bathrooms
Guests 8
15 reviews
Cozy Waterfront Home With Heated Pool.
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$107 avg/night
2 beds
2 Bathrooms
Guests 4
4 reviews
Dirct access to Charlotte Harbor, Pine Island Sound and Boca...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$174 avg/night
3 beds
2 Bathrooms
Guests 6
27 reviews
Snook's Landing Getaway On The Bay In Historic Matlacha
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$196 avg/night
2 beds
1 Bathroom
Guests 4
17 reviews
WATERFRONT AND BEAUTIFUL-COVERED DOCKAGE-QUICK BOAT...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$143 avg/night
3 beds
2 Bathrooms
Guests 8
12 reviews
Boaters paradise on Pine Island
Guests5
Bedroom1
Bathroom1
Wonderful 0 / 5
$50 avg/night
1 bed
1 Bathroom
Guests 5
Pine Island Waterfront Condo in Tropical Paradise (506)
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$150 avg/night
2 beds
2 Bathrooms
Guests 4
7 reviews
OLD FLORIDA - 1925 historic sugar cane plantation farm house
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$143 avg/night
2 beds
2 Bathrooms
Guests 4
3 reviews
Spacious Waterfront Canal Home with Dock
Guests5
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$108 avg/night
2 beds
2 Bathrooms
Guests 5
Canal Front Bokeelia Fishing Bungalow
Guests5
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$111 avg/night
2 beds
1 Bathroom
Guests 5
11 reviews
Stunning Tropical Waterfront Home - a Fisherman's Dream! (Marina...
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$182 avg/night
3 beds
3 Bathrooms
Guests 6
13 reviews
Incredible Matlacha Fishing and Outstanding Views
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$129 avg/night
1 bed
1 Bathroom
Guests 4
12 reviews
Beautiful, Spacious House With In Ground Pool In A Tropical...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$117 avg/night
3 beds
2 Bathrooms
Guests 6
12 reviews
Serenity abounds. Astounding sunsets, beautiful waters & perfect...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$124 avg/night
3 beds
2 Bathrooms
Guests 8
3 reviews
AWESOME MATLACHA HOME ON CANAL. WALK TO SHOPS, DINING, FISHING...
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$171 avg/night
2 beds
2 Bathrooms
Guests 4
3 reviews
Pool home~Steps to Pineland Marina, Alden Pines Golf & Tennis...
Guests6
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$144 avg/night
3 beds
3 Bathrooms
Guests 6
Nellie's Nest - 5 Min to Open Water! Five star reviews!
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$132 avg/night
2 beds
2 Bathrooms
Guests 6
67 reviews
Bokeelia Waterfront Townhome
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$129 avg/night
2 beds
2 Bathrooms
Guests 4
6 reviews
Bokeelia Hideaway Escape
Guests6
Bedrooms2
Bathrooms3
Wonderful 4.8 / 5
$170 avg/night
2 beds
3 Bathrooms
Guests 6
4 reviews
Pine Island Paradise Resort
Guests4
Bedroom1
Bathroom1
Wonderful 3.5 / 5
$114 avg/night
1 bed
1 Bathroom
Guests 4
7 reviews
Best Pine Island Location In The Beautiful Bocilla Island Club...
Guests6
Bedrooms2
Bathrooms3
Wonderful 4.7 / 5
$142 avg/night
2 beds
3 Bathrooms
Guests 6
11 reviews
CANAL LIFE on Matlacha !
Guests12
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$228 avg/night
4 beds
3 Bathrooms
Guests 12
5 reviews
Luxurious And Spacious Vacation Home In Bokeelia Florida.
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$167 avg/night
2 beds
2 Bathrooms
Guests 5
5 reviews
The Bokeelia Boathouse, waterfront, Pine Island, Florida
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$187 avg/night
2 beds
2 Bathrooms
Guests 6
20 reviews
Fishermen, Kayakers &Birdwatchers Paradise -Fish in 5 Minutes
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$141 avg/night
3 beds
2 Bathrooms
Guests 6
9 reviews
BOAT AND KAYAKS AVAILABLE!
Guests4
Studio
Bathrooms0
Wonderful 4.9 / 5
$80 avg/night
Studio
0 Bathrooms
Guests 4
14 reviews
The Victoria of Matlacha - Dolphin Suite
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$160 avg/night
1 bed
1 Bathroom
Guests 2
7 reviews
Canal Front Home In Beautiful St. James City
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$137 avg/night
2 beds
2 Bathrooms
Guests 4
5 reviews
A slice of paradise! Kick back and relax on Florida's largest...
Guests6
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$118 avg/night
2 beds
2 Bathrooms
Guests 6

Pine Island, Florida, USA Vacation Rentals

Enjoy Island Comfort

4 BR home for bird-watchers, nature lovers, boaters, in St Jame...

Pet friendly well located updated home with dock/lift on 8th Ave...

Enjoy Old Florida Island Life in St James City, FL-Sit and Watch...

NEW! Pine Island Vacation Pool Home on Canal w Dock - Natural...

Cozy Villa in the heart of Pine Island/Bokeelia.

Paradise Home with Private Pool & Boat Lift!

Available - Stunning location, Private Pool - Great Reviews

Peaceful Pine Island Captains Harbor Condo Located in South West...

Waterfront home with pool moments away from open water

Quaint Canal Home With Dock & Lift

Summer/Fall Special *$99* Private Pool - Beautiful Home

Perfect Quiet Location with Pool, Bring your boat and golf clubs...

Cutest Cottage Home in Matlacha

Welcome! Come stay and play, book now for great rates! Beautiful...

Birdwatchers Paradise

Immaculate Economy - Pine Island Warmth

Quaint 2 Bedroom 2.5 Bathroom Condo On Beautiful Pine Island...

**CALL FOR ACCURATE QUOTE!** 'Casa High Tide' Relax on Quiet...

JANUARY 2018 NOW OPEN!

* St James City * Waterfront * Completely Remodeled 2016 *

Bay-front Home With Spectacular Pool On One Of Florida's Best...

Cozy Waterfront Home With Heated Pool.

Dirct access to Charlotte Harbor, Pine Island Sound and Boca...

Snook's Landing Getaway On The Bay In Historic Matlacha

WATERFRONT AND BEAUTIFUL-COVERED DOCKAGE-QUICK BOAT...

Boaters paradise on Pine Island

Pine Island Waterfront Condo in Tropical Paradise (506)

OLD FLORIDA - 1925 historic sugar cane plantation farm house

Spacious Waterfront Canal Home with Dock

Canal Front Bokeelia Fishing Bungalow

Stunning Tropical Waterfront Home - a Fisherman's Dream! (Marina...

Incredible Matlacha Fishing and Outstanding Views

Beautiful, Spacious House With In Ground Pool In A Tropical...

Serenity abounds. Astounding sunsets, beautiful waters & perfect...

AWESOME MATLACHA HOME ON CANAL. WALK TO SHOPS, DINING, FISHING...

Pool home~Steps to Pineland Marina, Alden Pines Golf & Tennis...

Nellie's Nest - 5 Min to Open Water! Five star reviews!

Bokeelia Waterfront Townhome

Bokeelia Hideaway Escape

Pine Island Paradise Resort

Best Pine Island Location In The Beautiful Bocilla Island Club...

CANAL LIFE on Matlacha !

Luxurious And Spacious Vacation Home In Bokeelia Florida.

The Bokeelia Boathouse, waterfront, Pine Island, Florida

Fishermen, Kayakers &Birdwatchers Paradise -Fish in 5 Minutes

BOAT AND KAYAKS AVAILABLE!

The Victoria of Matlacha - Dolphin Suite

Canal Front Home In Beautiful St. James City

A slice of paradise! Kick back and relax on Florida's largest...

Summer/Fall Special $99 Private Pool - Beautiful Home

CALL FOR ACCURATE QUOTE! 'Casa High Tide' Relax on Quiet...