St. James City Pine Island Vacation Rentals & Private Rental Homes.
Book Your Pine Island Vacation Rental Home Here and Save!
Many properties to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit enjoyable.
Vacation Rentals by Owner in Pine Island Florida.
We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for places to rent in Pine Island, Florida.
New Construction Island Home / Heated Pool / Direct Gulf Access
Saint James City Private vacation home
Home away from home!
Luxury custom built waterfront home completed in 2022. All new furnishings arriving in June. Heated pool and direct access to the Gulf of Mexico. Safely dock your boat on our new 60\' dock. You are minutes from world class fishing and shelling. Sanibel, Captiva and Cayo Costa area a short boat ride away. Open .......read more
Saint James City
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8
3/3 AMAZING HEATED POOL HOME in St. James City!
Saint James City Private vacation home 
4.6 Star Review
Beautiful 3 bedroom 3 bathroom home off water with an heated amazing pool! Recently upgraded including a beautiful kitchen, 1 full bathroom downstairs, 2 full bathrooms upstairs and all 3 bedrooms are also located upstairs. Relax in the soaker tub in the master bathroom. Both guest bedrooms upstairs walk out onto a balcony overlooking the pool. Thi.......read more
Saint James City
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 7
Tiny Water Front Home
Saint James City Private vacation home 3.7 Star Review
Tiny waterfront home in a very quiet neighborhood. Fish from your own dock or take the 2 person kayak right out to Pine Island Sound. A short walk to several waterfront restaurants.
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NOTE: Although we are a "Superhost" for several Airbnb retreats from Florida to Nova Scotia, this is a new property for us, so until we get a .......read more
Saint James City
1 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 2
Wow stunning and world class fishing w boat lift
Saint James City Private vacation home 5.0 Star Review
Luxury waterfront home with heated pool, direct Gulf access with private docking for your boat. Open concept layout with 3 bedrooms and 3 baths. Custom built home with high end appliances and finishes. Start your morning with a coffee in the screened in lanai and watch the wildlife around you in the canal. This is also the final location to be at .......read more
Saint James City
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 8
Pelican`s Preserve in St. James City!
Saint James City Private vacation home 5.0 Star Review
Interested in a 30+ day rental? Please contact the manager for discounted monthly rates.
Enjoy this beautiful 2 bedroom 2 bath with a screened lanai and an open deck to enjoy views of the canal. Love boating? Bring your boat! Large dock and davits available for quick Gulf access on a deep canal. Bring your pets! There is a small enclosed f.......read more
Saint James City
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 4
2/2 Beauty with INCREDIBLE Gulf access, BOAT LIFT included!
Saint James City Private vacation home 4.0 Star Review
This gorgeous 2 bedroom, 2 bathroom home is waterfront with Direct Access to the Intra-coastal Waterway, your gateway to the Gulf of Mexico, Sanibel, Captiva, and Cayo Costa. Not only is this renovated home beautiful inside and out, it is also Pet Friendly! Bring your boat for some of the most renowned fishing in the country. Relax in style in th.......read more
Saint James City
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 4
Pine Island Retreat POOL HOME WITH BOAT LIFT!
Saint James City Private vacation home 4.5 Star Review
This immaculate 3 bedroom, 2 bathroom home is waterfront with Direct Access to the Intra-coastal Waterway, your gateway to the Gulf of Mexico, Sanibel, Captiva, and Cayo Costa. Not only is this newly renovated home beautiful inside and out, it is also Pet Friendly! Bring your boat for some of the most renowned fishing in the country. Relax in sty.......read more
Saint James City
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8
GORGEOUS 2/2 POOL HOME WITH AMAZING GULF ACCESS!
Saint James City Private vacation home 4.7 Star Review
Come and truly enjoy what Florida living is all about. This newly remodeled two bedroom 2 bathroom home is a pleasure to stay! Large pool with spacious lanai overlooking canal, windows from the kitchen that open wide to enjoy the nice salty breeze, french doors from the master bedroom to the lanai, firepit and much more! Lounge by the pool and en.......read more
Saint James City
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6
Newly Renovated 2/2 POOL Home with BOAT LIFT, INCREDIBLE ACCESS
Saint James City Private vacation home
Interested in a 30+ day rental? Please contact the manager for monthly rates.
This immaculate, newly renovated 2 bedroom, 2 bathroom home is waterfront with direct access to the Intra-coastal Waterway, your gateway to the Gulf of Mexico, Sanibel, Captiva, and Cayo Costa. Bring your boat for some of the most renowned fishing in the country. U.......read more
Saint James City
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 4
2/1 St. James Paradise with BRAND NEW POOL!
Saint James City Private vacation home 4.8 Star Review
Interested in a 30+ day rental? Please contact the manager for discounted monthly rates.
Enjoy your vacation in this light and cozy home. This two bed, one bath home is nicely decorated with a great enclosed lanai overlooking the brand new pool. Grill out in the back yard and watch for the dolphin to come in, or kayak down the long quiet.......read more
Saint James City
2 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 4
Manatee Bay Serenity
Saint James City Private vacation home 4.5 Star Review
You will truly feel as though you are staying in your home away from home when you stay in this beautiful manatee bay home. With a huge master suite, and the split ranch layout, it is perfect for all occasions. The guest rooms are also well appointed, once featuring two twin beds, and the third offering a queen bed. The main living spaces in .......read more
Saint James City
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6
Charming 3 bedroom with INCREDIBLE boating access in St. James City!
Saint James City Private vacation home
This charming 3 bedroom 2 bathroom home is canal front with direct access to the Intra-coastal Waterway, your gateway to the Gulf of Mexico, Sanibel, Captiva, and Cayo Costa. Bring your boat for some of the most renowned fishing in the country. Relax in style on the second floor lanai or enjoy the beautiful weather on the patio. St James City has a.......read more
Saint James City
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8
2/2 GORGEOUS home with Panoramic views of the water!
Saint James City Private vacation home 5.0 Star Review
This beautiful remodeled 2 bedroom 2 bathroom home offers panoramic views of the water! On a corner lot, plenty of room for a boat trailer. Brand new boat lift available for use with direct access to the Intra-coastal Waterway, your gateway to the Gulf of Mexico, Sanibel, Captiva, and Cayo Costa. Bring your boat for some of the most renowned fishin.......read more
Saint James City
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 4
GORGEOUS 3/2 ON WATER HOME WITH A BOAT LIFT!
Saint James City Private vacation home 5.0 Star Review
Interested in a 30+ day rental? Please contact the manager for discounted monthly rates.
Welcome to peace, welcome to paradise, welcome to PORCHFISH! This beautiful 3 bedroom, 2 bath home on Pine Island in St. James City is your vacation dream. This home is sure to please with like-new coastal décor and comfortable furnishings in a very p.......read more
Saint James City
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6
St. James City Vacation Home with Private Dock, Pool and Gulf Access
Saint James City Private vacation home 4.5 Star Review
St. James City Vacation Home with Private Dock, Pool and Gulf Access.
It\'s Rum and Reel Time! Located on Pine Island in St. James City, this is Island home is a 3 bedroom 2 bathroom private pool heated home with private boat dock, lift and a community boat launch, bring your own boat or use the kayaks provided for you. This home offers an .......read more
Saint James City
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6
Gorgeous canal front home located on Pine Island w/boat lift
Saint James City Private vacation home 5.0 Star Review
This premier waterfront home located on a deep water canal with 80 feet of sea wall with direct access to the Intracoastal. Newly remodeled kitchen, large lanai and its own private beach makes this property a unique tropical getaway!
Bring your boat and use the dock space provided. Only a short canal cruise to the outer islands, Gulf of Mexi.......read more
Saint James City
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6
2/2 Updated Home with Incredible View!
Saint James City Private vacation home 2.5 Star Review
This beautiful upgraded 2 bedroom 2 bath home in St. James City has everything you are looking for a relaxing island getaway. Brand new beautiful welly stocked kitchen, coastal vibes in the living room over looking the incredible view ane a bonus room with bunk beds. Bring your boat! Plenty of room to park a boat trailer, and large docks to tie up........read more
Saint James City
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6
Old Florida Charm in a small Boutique Motel "Cabana Suite"
Saint James City Villa 5.0 Star Review
Cabana Suite
Unique and charming inn on Pine Island. 120\' Dock, heated swimming pool. Close to restaurants, marinas. St James City is a golf cart friendly town! Rent a golf cart, bike or charter a boat to make you vacation even more memorable!
2 bedroom/1 full bathroom suite with a queen bed in the main bedroom and a queen murphy bed in .......read more
Saint James City
2 Bedroom(s) - 1 Bath(s)
Villa Rental Sleeps 6
Closest Inn to Deep Water in St James City - 2 mins to deep water! Great Views!
Saint James City Apartment 5.0 Star Review
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Lure Suite". Compared to any other Inn on Pine Island we can honestly say, "If you had stayed at the Southernmost, you could be fishing already!" Avoid the ten to fifteen minute boat ride up the canal\'s "no wake" zones.
Lure is a one-bedroom, o.......read more
Saint James City
1 Bedroom(s) - 1 Bath(s)
Apartment Rental Sleeps 4
Closest Inn to Deep Water in St James City - 2 mins to deep water! Great Views!
Saint James City Apartment
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Reel Suite". Compared to any other Inn in St. James City we can honestly say, "If you had stayed at the Southernmost, you could be fishing already!" Avoid the ten to fifteen minute boat ride up the canal\'s "no wake" zones.
Reel is a one-bedroom.......read more
Saint James City
1 Bedroom(s) - 1 Bath(s)
Apartment Rental Sleeps 6