St. James City Pine Island Vacation Rentals & Private Rental Homes.

Private Vacation Home in Saint James City

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 fence for them to enjoy.? Spend your winter in the perfect St James City neighborhood. Great Location!?Call to book this today!! 239-283-0909
*Please contac.......

5.0 Star Review

Condo in Saint James City

This beautiful 2 bedroom, 2.5 bath condo has everything you need to enjoy the island to the fullest!
Blue Crab Key is a beautiful resort style condo complex located in serene Bokeelia. It is in one of Pine Island's finest condo communities with two heated swimming pools and Jacuzzis, two tennis courts and a nice Clubhouse. It also features free boat dockage that is available on a first come first serve basis in this community, which offers direct access to Matlacha! There is plenty of space b.......

2 Bedrooms - Sleeps 4
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

Immaculate waterfront condo with one of the best views around. Direct access to Matlacha Pass and some of the worlds best fishing. This unit features 2 master bedrooms on the top floor with the living quarters on the main floor featuring a 1/2 bath. Come and relax in a beautiful, comfortable townhouse apartment located in a private enclave surrounded by canals and private boat docks. This town home has an AMAZING view of Pine Island Creek and Matlacha Pass. Boat out into the waters around Cayo C.......

2 Bedrooms - Sleeps 4
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

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 enjoy the peace in this quiet neighborhood, with walking distance to bars and restaurants. This two bedroom two bathroom waterfront home comes with plent.......

4.9 Star Review

Private Vacation Home in Saint James City

Welcome to Banana Haven! 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. Boat lift is included with property! Interested in a 30+ day rental? Please contact the manager for monthly rates........

2 Bedrooms - Sleeps 4
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

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 style on the air conditioned lanai or enjoy the beautiful weather on the patio. St James City has a ton to offer. There are several great restaurants and .......

4.2 Star Review

Condo in Saint James City

Beautiful, Bright & Airy Condo with Spectacular Views of Pine Island Creek. This beautiful 2 bedroom 2 and 1/2 bath condo is in one of Pine Island's finest condo communities. Enjoy spectacular views of Pine Island Creek and Matlacha Pass from your private screened lanai. On those extra warm summer days you can close the sliders on the porch and still enjoy the extended living space in the nice AC! Everything you need for the perfect vacation is in this beautifully updated condo. Awesome Applianc.......

2 Bedrooms - Sleeps 4
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

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 decor and comfortable furnishings in a very private setting. The large screened in porch overlooks the intersecting canals and protected mangroves which are filled with aquatic and aviary wildlife. Lookout for dolphins, manatees, bald eagles and blue herons as you sip your coffee or cocktail o.......

5.0 Star Review

Private Vacation Home in Saint James City

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 Mexico beaches, and great fishing........

5.0 Star Review

Private Vacation Home in Saint James City

Zuzu's Fancy is a wonderful 3 bedroom, 3 bathroom home in a quiet St. James City neighborhood. This home is sure to please with its beautiful coastal décor and comfortable furnishings. Dolphins are often seen playing in the back canal while manatees swim in the front canal by the fire-pit. This home offers a screened in porch overlooking the canal and mangroves, with a large Tiki Hut and large outdoor area. Bring your boat! You'll find a great canal side dock complete with water and electri.......

4.9 Star Review

Private Vacation Home in Saint James City

Escape to Pine Island for a waterfront stay at this 3-bedroom, 2-bathroom vacation rental! The bright, comfortable interior features a full, sleek kitchen and a cozy living area, while the outdoor space offers a furnished sunroom and patio with a fire pit! Head to nearby Monroe Canal Marina & Boat Rentals so you can explore on the water, adventure around Pine Islands Flatwood Preserve, or take the family to Sun Splash Family Waterpark. Memory-filled moments are just around the corner!

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5.0 Star Review

Private Vacation Home in Saint James City

Escape to The Hook Oar House, your perfect waterfront retreat for fishing, kayaking, and boating in St. James City, Florida.

Our immaculate 2-bed/2-bath elevated home offers easy access to Pine Island Sound and plenty of fish to be caught and dolphins/manatees to see.

Relax on the spacious deck or in our clean and comfortable living space, complete with modern amenities. Our new lower-level apartment provides additional space and privacy. You are only a short drive from the best r.......

2 Bedrooms - Sleeps 5
Vacation Rental in Saint James City

Apartment in Saint James City

This cozy efficiency apartment attached to the "Hook Oar House" has everything you need for a comfortable and relaxing stay. Whether you're a solo traveler or part of a group, this unit is the perfect spot to recharge after a long day of fishing or exploring the beautiful Pine Island Sound.

Recently remodeled after Hurricane Ian, this unit boasts brand new appliances and full kitchen amenities, including a Keurig coffee machine and propane grill to use. Plus, with the option to rent the .......

1 Bedrooms - Sleeps 2
Vacation Rental in Saint James City

Mobile Home in Saint James City

Quiet island living, with quick access to pine island sound from your dock. Great kyaking, fishing and 16 miles of safe bike path riding. Quaint waterside restaurants, all minutes from your Island Paradise ........

5.0 Star Review

Private Vacation Home in Saint James City

This beautiful upgraded 3 bedroom 2 bath pool home in St. James City has everything you are looking for a relaxing island getaway. This home is sure to please! Beautiful bright large kitchen, separate dining area to seat 6, king beds in two of the rooms a queen in the 3rd bedroom, and a comfortable living area with flat screen t.v. Enjoy lounging by the heated pool, or soaking in the adjoined hot tub. This home is located in the center of Pine Island. Just a short drive away from St. James City.......

3 Bedrooms - Sleeps 6
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

Welcome to @TheGulfGetaway an incredible canal-side home built to make memories. You'll enjoy the comfort of a fully equipped home and many outdoor activities. House is within walking distance from bars & restaurants and has quick access to the Gulf of Mexico & nearby islands of Sanibel, Captiva & Cayo Costa by boat.
Centered in a quiet familial neighborhood, the location of the home makes it easy to get around.
1 hr from Ft Myers Airport
The space
Spacious three bedroom two bath ho.......

5.0 Star Review

Private Vacation Home in Saint James City

This home has it all: Direct Five Minute Access, Boat Dock-Lift Optional, Quiet Neighborhood, Restaurants and Pubs within minutes by car or boat. Bring your boat and run over to Sanibel, Captiva, Cayo Costa, Boca Grand, etc.
This home has 2 bedrooms and 2 baths with a modern full-sized, well-equipped Kitchen with a separated dinning area. The Sun Room is a nice place to enjoy the view and sunset while sitting in the A/C. Quiet street, nice waterfront neighborhood. Close to the local fish hou.......

4.9 Star Review

Private Vacation Home in Saint James City

There is nothing better than slipping away to your tropical paradise vacation home knowing that everything is in tip top shape. This is exactly what you will find in this newly built 3 bedroom, 2 bath pool home in St. James City. This home is outfitted with granite counter tops, tile throughout, a screened lanai with a heated pool, hot tub, and a boat dock. Minutes out to the Gulf! With three bedrooms there is plenty of room for the whole family. *Boat lift is unavailable at this property. Welc.......

3 Bedrooms - Sleeps 8
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

Grandpa Rudy first came to Pine Island in 1954 and our family has been coming ever since! Grab a cup of coffee (tea or adult beverage) and take a seat around the fire pit, the walk-around deck, or anywhere on the property that the fruit and coconut trees grow to start your "island time".

The Key West style home is one of the only 4 bedroom, 4 bath homes for rent on the island. 2 master bedrooms and a 3rd bedroom with twin beds are on the main level. A separated 4th is bedroom is downst.......

4.1 Star Review

Private Vacation Home in Saint James City

Welcome to Mermaid Haven! This property is undeniably a vacation renters dream home. As you walk through the front door, you are welcomed by beautiful coastal décor, upgraded kitchen and bathrooms, and incredible design. This property welcomes large or multiple families. Upstairs there are 3 bedrooms, 2 bathrooms, full kitchen, laundry, screened in balcony overlooking the canal and a hot tub. Located downstairs are separate living quarters, as we call the Mother-In-Law suite. Full kitchen, livi.......

5.0 Star Review

Mobile Home in Saint James City

Cute, clean and comfy 2 bed, 2 full bath mobile home in Saint James City, Florida on a quiet canal with 8000 pound boatlift and only a 15 minute troll out to open water, and all the beautiful beaches of Sanibel and Captiva. Enjoy the fishing and relax on the screened-in porch overlooking the dock or take a nap in the air conditioning on the large couch or in one of the two recliners. Eat-in kitchen also overlooks the canal and is perfect for watching the sunsets.

Boat lift will accommod.......

4.7 Star Review

Mobile Home in Saint James City

Bring your own boat or rent one while you stay and play. Close to the gulf with easy access by boat. Great for water recreation and fabulous fishing. This quaint little Pine Island village is recovering quickly from the wrath of Hurricane Ian in 2022. Many bars and restaurants are open and waiting for your arrival. This 2 bedroom, 2 bath private home is comfy and coastal, fully furnished, with lots of sunshine pouring through the windows........

2 Bedrooms - Sleeps 4
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

?Unique and tranquil getaway. No hurricane damage
?Heated pool on the water… make your families dream vacation!
?Private home tucked away in your own spot on this exclusive island.
??‍♂️5 bedrooms, massive kitchen and living area overlooking the waterway you can kayak or Boat or Ferry ride to private sand beaches, restaurants and the best fishing in Florida. ?
? Second kitchen for cooking big meals or storing extra snacks and drinks by the pool. ***NEW POOL TABLE added! Pictu.......

5 Bedrooms - Sleeps 14
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

Two bedroom two bath incredible home with water views from all angles! Large lot including, tiki wet-bar, and small boat house with an ice machine & bathroom! Plenty of space on pavers for additional parking, boat trailer, or even corn hole! Sip coffee on the beautiful wrap around fully screened in porch while watching the dolphins and manatees float by. Large enough for 6 guests are the first bedroom has a murphy bunk bed available. Wrap around porched, fully screened. Bring your boat! Boat lif.......

4.8 Star Review

Private Vacation Home in Saint James City

Come and enjoy this amazing location! The house is cozy and inviting, with a nice view of the canal, easy access to the golf waters for an amazing day of fishing. Close to Bars with live music, boat ramps, kayak rentals and many other attractions.
The house ? is ready for your enjoyment, you will find on it:
* 2 Kayaks
* 1 pedal boat
* 2 bikes ?
* 1 golf car
* Jacuzzi Spa Pool 8 x 14ft
* 10000-pound boat lift
* Fishing rods ?
* Smart TVs

If you have.......

4.9 Star Review

Private Vacation Home in Saint James City

Villa Boat House

Escape to paradise with this petite retreat villa featuring a private Pool & DIRECT Gulf Access! Villa Boat House will leave you savoring all of what Southwest Florida has to offer. You and your loved ones will be immersed in a boaters paradise from the second you open the front door. This 3 Bedroom – 2 Bathroom villa boasts just under 1400 sq ft of coastal decor & space, with sleeping capabilities for 6! With just 5-10 minutes out to open water and close proximity to .......

4.4 Star Review

Private Vacation Home in Saint James City

Welcome to the Flamingo Hideaway! This is the perfect island vibe vacation rental! Beautiful old Florida charm with bright colors, flamingo decor and modern finishings. This property has 3 bedroom and 2 baths. Two bedrooms offer queen beds while the third has two twin beds. Fully stocked kitchen, grill and ever a margarita mixer! Bring your boat! Quick access to the gulf of Mexico, boat lift is included with rental!.......

5.0 Star Review

Private Vacation Home in Saint James City

This 3 bedroom 2.5 bath home is the perfect spot for relaxation. Bring your boat or enjoying the two kayaks this property offers! Plenty of space to tie your boat up! Lower dock to easily drop a kayak in. Located on a deep canal in St. James City, you will be out in the Gulf within minutes. Relax pool side with the whole family, this home is large enough to accommodate all. Located on a corner canal, the water views are endless! **THIS PROPERTY NOW HAS A FULL SCREENED IN LANIA ON THE POOL DECK. .......

3 Bedrooms - Sleeps 6
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

Come relax in our Pine Island dream home--a charming, open and colorful floor plan will remind you that you are on a Florida vacation at every turn. Watch a thunderous storm from the furnished lanai, or fish for snook, snapper, crab, and shark from our dock. If you are lucky, catch a glimpse of dolphin or shark circling our fish light at night. Enjoy a peaceful stroll or bike ride to several restaurants and bait stores a few blocks away. World class beaches can be found by a ten minute boat .......

5.0 Star Review

Private Vacation Home in Saint James City

Slip on your flip flops and grab your sunscreen, as this 3-bedroom, 2-bath Saint James City vacation rental awaits! The home sits right on the canal with easy access to open water and nearby marinas if you’d like to try your hand at boating. There are also waterfront restaurants, family-friendly waterparks, and sunny beaches within a short drive, so the entertainment is truly endless! Stay at home to roast s’mores over the fire pit, barbecue on the patio, or spot visiting manatees in the can.......

4.8 Star Review

Private Vacation Home in Saint James City

Come and enjoy this amazing location! The house is cozy and inviting, with a nice view of the canal, easy access to the golf waters for an amazing day of fishing. Close to Bars with live music, boat ramps, kayak rentals and many other attractions.
The house ? is ready for your enjoyment, you will find on it:
* 2 Kayaks
* 1 pedal boat
* 2 bikes ?
* 1 golf car
* Jacuzzi Spa Pool 8 x 14ft
* 8000-pound boat lift
* Fishing rods ?
* Smart TVs

If you have .......

5.0 Star Review

Private Vacation Home in Saint James City

Villa The Reel It Inn

Introducing a brand new vacation home that is a fishing aficionado's dream come true! This stunning property combines luxurious amenities with a passion for fishing, ensuring an unforgettable getaway.

This home is a " Reel Catch"! Situated in one of the most popular fishing islands in the world, you have dock access and are only 5 minutes to open water!

For moments of ultimate relaxation, a 5 person hot tub with waterfall and light show awaits you. Imm.......

3 Bedrooms - Sleeps 6
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

Welcome to Island Vibe! Brand new look! Gorgeous 3 bedroom two bath with heated salt water pool with incredible Gulf access is your perfect Pine Island getaway! This home was just remodeled into this bright, fun, colorful ambiance with everything you need in a vacation rental. The kitchen is fully equipped, washer and dryer included, cable and fast internet, fire pit, outdoor games and more! Flat screen smart tvs in every room, cable is available in the living room. There is a bonus room includi.......

4.7 Star Review

Mobile Home in Saint James City

3/2 home in Flamingo Bay, Pine Island! On the water, with the plenty of space for a boat trailer and an area to tie up on the boat! Flamingo Bay is center of the island with easy access on and off the island and close to local restaurants. This property is pet friendly, bring your pup! The property offers 3 bedrooms and 2 bathrooms. Outdoor deck to enjoy your coffee every morning over looking the canal........

3 Bedrooms - Sleeps 6
Vacation Rental in Saint James City

Private Vacation Home in Saint James City

White Sands is a luxury custom built waterfront home completed in 2022. Heated pool and direct access to the Gulf of Mexico. Safely dock your boat on our new 60' dock with a fish cleaning station. Plenty of room for trailers under the house. You are minutes from world class fishing and shelling. Sanibel, Captiva and Cayo Costa are about a 10 minute boat ride away. The home offers an open concept with 3 bedrooms, 2 bath and a pullout sleeper couch in living room. The home has security cameras .......

5.0 Star Review

Private Vacation Home in Saint James City

Our beautiful newly remodeled home away from home is located in St. James City, Florida. Just minutes away from Sanibel Island and Fort Myers Beach by boat. The living area is very spacious with a leather sectional and recliner with a 65" tv. The kitchen has a large island for great entertaining or just hanging out.

Our home is three bedroom, three and a half bath, all master suites with your very own bathroom.
The first bedroom has a king bed and the bath has a shower and double si.......

3 Bedrooms - Sleeps 6
Vacation Rental in Saint James City