Saint James City vacation rentals

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Top-rated vacation rentals in Saint James City

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Matlacha

4.88 out of 5 average rating, 133 reviews

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

Nov 4 – 11

R2,178 ZAR per night

Guest favorite

Apartment in Saint James City

4.93 out of 5 average rating, 84 reviews

Island Castaway--Free Kayaks

This is the perfect place to sit back, relax and enjoy the view. You have the privacy of a one-bedroom apartment with small kitchen and bath. We are close to great restaurants and some of the best music on the island. Open water and excellent fishing are minutes away. Two kayaks are set up for fishing and are available for guests to use so bring your fishing rod. Pine Island has no beachs, but Ft Myers Beach is about an hour away or take a ferry ride from Bokeelia to Cayo Costa for the day.

Nov 12 – 19

R2,166 ZAR per night

Guest favorite

Home in Saint James City

4.94 out of 5 average rating, 53 reviews

🌴ISLAND TIME! DOCK⚓️POOL🏊🏻‍♀️KAYAKS🛶Boat to Beach🏖 Pets

DIRECT GULF ACCESS HOME - Step back in time, recharge yourself on ISLAND TIME! Pine Island is a laid back Old Florida atmosphere where you can get away from it all. 4 beds, 2 full baths. Steps to your dock & canal. Sandy secluded Beaches are minutes away by boat! Island Hopping! Don't have a boat, no worries-water taxis & rentals are plentiful on the Island. 4 seat Golf cart available. Steps to our private community pool & jet tub! Bikes & Kayaks & Games included.Sit back & relax! It's time 🌴🐠

Dec 11 – 18

R2,499 ZAR per night

Guest favorite

Cottage in Bokeelia

4.99 out of 5 average rating, 109 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. The dock is shared, but there is plenty of room! Lots of history on this beautiful island, with fishing you’ll be amazed with! Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources!

Aug 4 – 11

R3,855 ZAR per night

Guest favorite

Cottage in Saint James City

5.0 out of 5 average rating, 25 reviews

Waterside Cottage

Enjoy our peaceful little island paradise nestled beneath sprawling oaks and scattered palms just minutes from St James City’s restaurants and bars. Just under 1/2 acre is yours to enjoy. Watch the manatees and dolphins swimming in the canal while you grill your catch of the day, or your fresh pick of the day from St James Fish House just down the street! Inside enjoy a fresh new contemporary and stylish cottage with everything you will need to make your stay comfortable, enjoyable and fun!

Nov 5 – 12

R3,750 ZAR per night

Guest favorite

Home in Bokeelia

4.91 out of 5 average rating, 54 reviews

Cozy Duplex in the Heart of the Island

Enjoy the beautiful Florida weather on our screened front porch furnished with a dinning table and chairs gives you the option of dinning outside while enjoying Florida weather. The duplex has a one bedroom with a queen bed and on-suite bathroom. The room next to it has a sofa bed with TV and internet. A full size kitchen with all the utensils needed to cook any meal are at your disposal. The neighborhood is quiet and you are walking distance from most amenities. Relax and enjoy the weather.

Jul 21 – 28

R2,421 ZAR per night

Guest favorite

Home in Saint James City

5.0 out of 5 average rating, 12 reviews

Island Retreat

Welcome to paradise in Pine Island, Florida! This stunning 3 bedroom, 2 bathroom house is the ultimate vacation rental for those seeking a tranquil and waterfront experience. Relax with the whole family at this peaceful retreat. Visit our IG page at PineIsland_Retreat for photos, information and vacation ideas. Long Stay Discounts applied for stays of 7 nights or more. Discounts vary by stay. Longer Stay, Greater Discounts! Early Bird Discounts available for 2025-2026 bookings. Book Today!

Nov 29 – Dec 6

R3,192 ZAR per night

Guest favorite

Home in Matlacha

4.95 out of 5 average rating, 127 reviews

Matlacha H2O! - Lovely, Relaxing & FREE KAYAK!

Matlacha is for LOVERS! Lovers of relaxation, fishing, art, nature, friends, social scenes and enjoying Life in this beautiful location. Perfect for a couple+ to enjoy the water and the Matlacha scene and out-islands and InterCoastal waterways. Close to everything - walk everywhere or take the free kayak out for expeditions or fishing. This 60 year old beautifully remodeled fishing cottage is clean and completely equipped with everything you need for FUN other than food and consumables.

Jun 17 – 24

R2,410 ZAR per night

Superhost

Home in Saint James City

New place to stay

Panoramic Views & Heated Pool!

Entire 3/2 home ON the water! STUNNING views of the Sanibel Causeway to Carlos Bay! A short boat ride to Sanibel & Captiva! Recently remodeled with NEW EVERYTHING and decorated beautifully! Large open living/kitchen/dining area with lots of seating. It has sliding glass doors that open fully to enjoy an all encompassing indoor/outdoor entertaining space! Everything you need for your short or long-term stay! You'll get the best sleep on these comfy beds! Coffee? Keurig & Nespresso machine.

Sep 26 – Oct 3

R13,110 ZAR per night

Guest favorite

Farm stay in Saint James City

5.0 out of 5 average rating, 44 reviews

Private entire cottage on unique horse farm

Relax and unwind at this private and unique cottage on a beautiful horse farm. Close to dining, shopping, a variety of boating, fishing, and other water activities. Visit the Matlacha Bridge to cast a line with other fishing enthusiasts, or take a leisurely bike ride to tour the island (bikes/helmets provided). Grab a water taxi and visit surrounding sister islands with beautiful, secluded beaches. Please see the host guidebook for places to eat, things to do, and best ways to get there.

Aug 27 – Sep 3

R3,060 ZAR per night

Guest favorite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 315 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Oct 29 – Nov 5

R1,720 ZAR per night

Guest favorite

Home in Matlacha

5.0 out of 5 average rating, 140 reviews

The Secret Island Retreat HeatedPool/4b/open water

Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a den, 3 bath, 2 car garage. 3200 sq ft. 2nd floor has an oversize owners suite with picture windows over the bay and provides an abundance of space for sitting area or quiet space. Three guests rooms + den. Don't forget to relax & enjoy the breeze on the 2nd story balcony...the perfect retreat. Kayaks, 2 boat lifts, fishing poles, bicycles, games, Grill and much more.

Jul 30 – Aug 6

R8,441 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Saint James City vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Saint James City's top sights

Woody's Waterside Island Bar & Grill52 locals recommend

Ragged Ass Saloon32 locals recommend

The Waterfront Restaurant & Marina37 locals recommend

Winn-Dixie34 locals recommend

Low Key Tiki41 locals recommend

Galt Preserve13 locals recommend

Other great vacation rentals in Saint James City

Guest favorite

Home in Bokeelia

5.0 out of 5 average rating, 5 reviews

*Newly Renovated* Fishing Getaway Near Boat Ramps

Jul 21 – 28

R2,037 ZAR per night

Guest favorite

Home in Matlacha

4.96 out of 5 average rating, 24 reviews

Fisherman's Cottage at Matlacha

Jun 16 – 23

R2,643 ZAR per night

Guest favorite

Home in Matlacha

5.0 out of 5 average rating, 17 reviews

Bayshore Bungalow - 1 bedroom

Dec 17 – 24

R2,183 ZAR per night

Guest favorite

Apartment in Bokeelia

5.0 out of 5 average rating, 12 reviews

Apartment at Treehouse Permaculture Farm

Aug 24 – 31

R2,953 ZAR per night

Guest favorite

Home in Matlacha

4.93 out of 5 average rating, 30 reviews

Matlacha Waterfront Fisherman’s Escape

Jun 8 – 15

R2,429 ZAR per night

Guest favorite

Home in Saint James City

5.0 out of 5 average rating, 31 reviews

Gulf getaway! Boat dock, heated saltwater pool

Aug 22 – 29

R4,984 ZAR per night

Superhost

Apartment in Bokeelia

4.87 out of 5 average rating, 45 reviews

Doublemint Duplex B - Cozy & Stylish Getaway!

Jun 7 – 14

R2,211 ZAR per night

Guest favorite

Home in Bokeelia

4.97 out of 5 average rating, 31 reviews

Relaxing island home near marina and boat ramp

Apr 18 – 25

R3,068 ZAR per night

Show all

Other great vacation rentals in Saint James City

Guest favorite

Home in Bokeelia

4.78 out of 5 average rating, 51 reviews

Island Retreat

Sep 22 – 29

R2,421 ZAR per night

Superhost

Home in Matlacha

4.8 out of 5 average rating, 15 reviews

Island Romp

Apr 27 – May 4

R2,651 ZAR per night

Guest favorite

Vacation home in Saint James City

4.86 out of 5 average rating, 7 reviews

Waterfront Efficiency Apartment

Oct 1 – 8

R2,416 ZAR per night

Guest favorite

Apartment in Bokeelia

5.0 out of 5 average rating, 49 reviews

Bokeelia , Florida - Suite/ apartment, w/ Pool.

Nov 23 – 30

R2,395 ZAR per night

Guest favorite

Cottage in Matlacha

4.86 out of 5 average rating, 85 reviews

A Hidden Gem Waterfront Retreat Matlacha Island!

Dec 25 – Jan 1

R2,799 ZAR per night

Guest favorite

Home in Bokeelia

4.91 out of 5 average rating, 32 reviews

NEW- Sunny Island Cottage w/ Large Patio

May 2 – 9

R2,183 ZAR per night

Guest favorite

Home in Matlacha

4.88 out of 5 average rating, 34 reviews

Sunset Waterfront Retreat with Kayak

Jun 23 – 30

R2,943 ZAR per night

Guest favorite

Apartment in Matlacha

5.0 out of 5 average rating, 26 reviews

Nature Lover's Paradise - Sea Sprite in Matlacha

Jun 4 – 11

R1,959 ZAR per night

Show all

Quick stats about vacation rentals in Saint James City

Total rentals	150 properties
Rentals with a pool	60 properties have a pool
Pet-friendly rentals	60 properties allow pets
Family-friendly rentals	120 properties are a good fit for families
Total number of reviews	2.1K reviews
Nightly prices starting at	R1,329 ZAR before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Saint James City?
Yes! Work meets play with ease at over 60 vacation rentals in Saint James City featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Saint James City?
Four-legged friends are welcome in Saint James City. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there Saint James City vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Saint James City, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Saint James City have air conditioning?
Absolutely! We offer over 110 house rentals with air conditioning in Saint James City. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Saint James City have wifi?
Absolutely! We offer over 110 house rentals with wifi in Saint James City. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Saint James City?
Saint James City has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Saint James City have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Saint James City. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Saint James City?
Experience the best of Saint James City with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Saint James City vacation rentals

Top-rated vacation rentals in Saint James City

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Saint James City vacation rentals

Stay near Saint James City's top sights

Other great vacation rentals in Saint James City

Home in Bokeelia

Home in Matlacha

Home in Matlacha

Apartment in Bokeelia

Home in Matlacha

Home in Saint James City

Apartment in Bokeelia

Home in Bokeelia

Other great vacation rentals in Saint James City

Home in Bokeelia

Home in Matlacha

Vacation home in Saint James City

Apartment in Bokeelia

Cottage in Matlacha

Home in Bokeelia

Home in Matlacha

Apartment in Matlacha

Quick stats about vacation rentals in Saint James City

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Saint James City?

Are there pet-friendly vacation rentals in Saint James City?

Are there Saint James City vacation rentals on Airbnb with pools?

Do house rentals in Saint James City have air conditioning?

Do house rentals in Saint James City have wifi?

Are there family-friendly house rentals in Saint James City?

Do house rentals in Saint James City have a bbq area?

How much does it cost to stay in house rentals in Saint James City?

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