Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $251 per night (USD)VRBO
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to this lovely apartment in Bokeelia. The apartment is a completely separate unit with private entrance and pool ...
From $251 per night (USD)VRBO
From $260 per night (USD)Expedia
NEW! Tropical Oasis with Private Screened Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a tropical paradise at this charming retreat in Saint James City! Nestled on the picturesque Myers Lane, this ...
From $260 per night (USD)Expedia
From $402 per night (USD)VRBO
Osprey Lake House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This stunning lake front vacation rental in Southwest Florida features a heated pool, a built-in grill and outdoor kitch ...
From $402 per night (USD)VRBO
From $216 per night (USD)Expedia
Island cottage 2 bedroom house in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Matlacha, this enchanting 2-bedroom house offers an amazing retreat for guests. With a king bed and queen bed ...
From $216 per night (USD)Expedia
From $326 per night (USD)VRBO
Best Kept Secret #SJC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Saint James City at this pleasant house. Family friendly spacious home, with 3 bedrooms and ...
From $326 per night (USD)VRBO
From $428 per night (USD)Expedia
Gorgeous 3\/2 Waterfront Home with Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to 'In July, a lemonade'! This 3 bedroom 2 bathroom home has been completed renovated top to bottom. This stilt ...
From $428 per night (USD)Expedia
From $350 per night (USD)VRBO
The Jade House in Beautiful St James City
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Unwind in Saint James City at this lovely house. With 3 bedrooms including 2 queen beds and 1 bunk bed, this property of ...
From $350 per night (USD)VRBO
From $216 per night (USD)Expedia
For Rent: 3Bed\/2Bath Waterfront Oasis in Bokeelia, FL!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a peaceful retreat on Pine Island? Experience Bokeelia like a local, this stunning 3-bedroom, 2-bath home is ...
From $216 per night (USD)Expedia
From $260 per night (USD)VRBO
Beautiful home with access to private beach, pool and hot tub.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Consider this townhome your home away from home while you visit Bokeelia. With 3 cozy bedrooms including a king, queen, ...
From $260 per night (USD)VRBO
From $240 per night (USD)Expedia
Matlacha Palms - Direct Gulf Access - Near Burnt S
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to Matlacha Palms Matlacha Palms is a gorgeous, and cozy tree-bedrooms, 2 full bathroom vacation villa situated ...
From $240 per night (USD)Expedia
From $293 per night (USD)VRBO
The Monroe Lookout! 2\/2 Pool Waterfront Home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Beautiful heated pool waterfront home in St. James City! This property offers 2 bedrooms and 2 bathrooms, large living s ...
From $293 per night (USD)VRBO
From $215 per night (USD)Expedia
3-bedroom pool house on manatee-filled canal. BYOB: Bring your own boat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the beauty of Saint James City from this modern, updated 3-bedroom house in the Manatee Bay subdivision. Inside ...
From $215 per night (USD)Expedia
From $167 per night (USD)VRBO
Bocillia Island Club Unit C-13
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to the charming Bocilla Island Club and discover the ultimate island getaway. This beautifully decorated vacation ...
From $167 per night (USD)VRBO
From $173 per night (USD)Expedia
Captains Harbor Island Hide Away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is one of Pine Island's most stunning and modernized two-bed and two-bath condo is waiting for you to live your bes ...
From $173 per night (USD)Expedia
From $132 per night (USD)VRBO
Furnished 2-bedroom condo in Bokeelia with, boat dock, pool, storage unit, etc.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Seasonal rental. Experience Bokeelia like a local in this 2-bedroom condo. This wonderful property features 1 king bed a ...
From $132 per night (USD)VRBO
From $293 per night (USD)VRBO
Fishing inshore, offshore, with easy access to Charlotte Harbor and Gulf.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Recently renovated cottage with three bedrooms located on the tip of Pine Island. Go boating in Charlotte Harbor with qu ...
From $293 per night (USD)VRBO
From $270 per night (USD)VRBO
Pool home with Dock - March booking special!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom pool home on deep Monroe Canal. Put your boat int he water at the house and avoid the ramp each day ...
From $270 per night (USD)VRBO
From $240 per night (USD)Expedia
LOCATION Cozy bungalow on Monroe Canal, the most entertaining \/ traveled canal
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Come enjoy island time year-round and soak up the laid-back island vibes from this newly renovated, cozy bungalow situat ...
From $240 per night (USD)Expedia
From $236 per night (USD)VRBO
Bokeelia Oasis! Heated Pool, Sleeps 12!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to this stunning tropical retreat in Bokeelia, where relaxation meets luxury! This beautifully designed home feat ...
From $236 per night (USD)VRBO
From $766 per night (USD)Expedia
Shellabration - Ocean Views and Family Fun!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: 🏡 Spacious luxury home – ensuite baths in every bedroom 🌊 Breathtaking ocean & preserve views 🏖 Beach-ready! ...
From $766 per night (USD)Expedia
From $876 per night (USD)VRBO
4-bedroom Screened in Pool House with Bar! Golf Carts, Roof Top, and Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Island Time Beach House – Your Ultimate Getaway on North Captiva Island! Welcome to Island Time Beach House, a newly re ...
From $876 per night (USD)VRBO
From $571 per night (USD)Expedia
New! Waterfront home-poker room-Boat dock & HIDDEN ROOM Walk 2 town. FABULOUS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Its all about the WOW!! Your Matlacha adventure begins at this chic 3-bedroom 3 full bath house. This home has been rebu ...
From $571 per night (USD)Expedia
From $1058 per night (USD)VRBO
ON THE BEACH, HEATED POOL, 4 KAYAKS, 5 LUXURY KING SUITES ALL WITH BATHS
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
HOMEAWAY "TRAVELER FAVORITE" AWARD RECIPIENT NOVEMBER 2018, OWNER MANAGED * ALWAYS CLEANED AND SANITIZED BY A PROFESSION ...
From $1058 per night (USD)VRBO
From $141 per night (USD)Expedia
Pine Island Breeze where you can relax, swim, fish, see dolphins and manatees!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Pine Island Breeze, an island experience without leaving the country. Great place to relax, swim, fish, bike ride, explo ...
From $141 per night (USD)Expedia
From $296 per night (USD)VRBO
Pine Island canal home with boat access to Gulf.\n\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your morning coffee with spectacular sunrises looking down the canal. Typical Florida landscaping with palm trees, ...
From $296 per night (USD)VRBO
From $399 per night (USD)Expedia
Casita Salida del Sol-North Captiva Island Waterfront townhouse w\/dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to "Casita Salida del Sol", your private sanctuary nestled on the pristine shores of North Captiva Island, Flori ...
From $399 per night (USD)Expedia
From $394 per night (USD)VRBO
Waterfront Paradise, 2\/2 Heated Pool, Tiki Hut & Stunning Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this gorgeous 2/2 waterfront retreat, featuring a brand new heated pool and a spacious lanai with outdoor seat ...
From $394 per night (USD)VRBO
From $218 per night (USD)Expedia
2-bedroom waterfront home with gulf access and close to bars and restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax with the entire family at our peaceful getaway. Enjoy nature at its finest, as you might be greeted by manatees, d ...
From $218 per night (USD)Expedia
From $1309 per night (USD)VRBO
Lookout Escape: Private Island Luxury*Gulf Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: 🌅 360° Gulf-to-Bay Views 🎉 Outdoor Paradise: Pool, Bar, Dart Boards, TVs, Games, Outdoor Shower, Bikes+ 🏖️St ...
From $1309 per night (USD)VRBO
From $419 per night (USD)Expedia
Spacious \"Crab Cakes\" Cottage on beautiful North Captiva Island,FL with GolfCart
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Crab Cakes Cottage on North Captiva Island, your perfect getaway destination! Nestled on a tranquil street, j ...
From $419 per night (USD)Expedia
From $238 per night (USD)VRBO
Off the Charts Inn - King Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the ultimate luxury in our expansive King Suite! Indulge yourself in the grandeur of a king-sized bed, comple ...
From $238 per night (USD)VRBO
From $219 per night (USD)Expedia
Off the Charts Inn - Standard Queen room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the sheer bliss of this spacious haven, complete with a fully equipped kitchen for your convenience. ...
From $219 per night (USD)Expedia
From $238 per night (USD)VRBO
Off the Charts Inn - Queen Double Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the ultimate comfort and luxury in our expansive Queen double bed room! Immerse yourself in the sheer bliss o ...
From $238 per night (USD)VRBO
From $278 per night (USD)Expedia
Pet friendly 3 bedroom, 2 bath pool home with direct access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this pet-friendly home, eagerly awaiting your arrival. With three bedrooms and two full baths, it provides a ...
From $278 per night (USD)Expedia
From $206 per night (USD)VRBO
Cozy home in Matlacha on the water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
comfy 2 bedroom 2 bathroom house in matlacha. House has beautiful kitchen and bathrooms. This home also is on the water ...
From $206 per night (USD)VRBO
From $161 per night (USD)VRBO
Island Getaway, with boat ramp access nearby. You can park your boat on property
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relaxing is an understatement. Perfect island getaway from the city. It's good for retirees to families. Island culture ...
From $161 per night (USD)VRBO
From $267 per night (USD)VRBO
Studio#1-Back Bay Sunsets in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take it easy at this unique and tranquil open water getaway - perfect for the solo traveler or a couple. Oversized close ...
From $267 per night (USD)VRBO
From $154 per night (USD)Expedia
1 Mi to Boat Ramp: Bokeelia Home w\/ Screened Patio
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Seeking a coastal adventure filled with sunshine and good times? Look no further than this 2-bedroom, 1-bathroom vacatio ...
From $154 per night (USD)Expedia
From $1125 per night (USD)VRBO
Escape to CASA PALMA HIDEAWAY! 4BD\/3BA, Pool, Outdoor Kitchen, boat slip & More!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This enchanting 4-bedroom, 3-bathroom retreat is a harmony of comfort and luxury, promising an unforgettable escape. On ...
From $1125 per night (USD)VRBO
From $137 per night (USD)Expedia
Island Cottage in Bokeelia - close to fishing and water sports!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom/one bath island cottage close to public boat ramp; fishing dock and marina. Down the street from kayak and p ...
From $137 per night (USD)Expedia
From $158 per night (USD)VRBO
Amazing Stay in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautifully renovated studio has everything you need for a fabulous stay in Matlacha. It is located on a quiet/peac ...
From $158 per night (USD)VRBO
From $223 per night (USD)Expedia
Off the Charts Inn King Efficiency
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the epitome of luxury with our King Efficiency suite. Indulge in the grandeur of a spacious king bed, a cozy ...
From $223 per night (USD)Expedia
From $294 per night (USD)VRBO
Dog-friendly waterfront home with heated pool, lanai, central AC, & W\/D
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beverly's Tarpon Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $294 per night (USD)VRBO
From $518 per night (USD)Expedia
Casa Florida 🌴 waterfront home with boat ramp
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
☞ Wifi ☞ Free boat ramp ☞ Walk Score 70 (Walk to cafes, dining, shopping etc.) ☞ 50” Smart TV ☞ Private patio w/ seatin ...
From $518 per night (USD)Expedia
From $892 per night (USD)VRBO
NEW LISTING! BEACH PARADISE: BEACHFRONT, SLEEPS 10, 2 CARTS, POOL, GAMES, & FUN
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Introducing Beach Paradise: A Luxurious Beachfront Retreat on North Captiva Island, Now Available for your next vacation ...
From $892 per night (USD)VRBO
From $195 per night (USD)VRBO
New Home in the heart of Pine Island. Private & Pet Friendly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to the island! Where the pace slows to a crawl and umbrella drinks await youEasy walk to swimming, tennis and s ...
From $195 per night (USD)VRBO
From $991 per night (USD)VRBO
NORTH CAPTIVA PEARL - Newly Completed multi level - Two Golf Carts - Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This newly completed, professionally designed multi-level, multi-deck home is located just 300 feet from the widest beac ...
From $991 per night (USD)VRBO
From $307 per night (USD)VRBO
Beautiful waterfront home with heated pool, dock, bikes, and kayaks!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hello and thank you for looking into Casa High Tide!! New owners have recently made lots of upgrades to this wonderful ...
From $307 per night (USD)VRBO
From $281 per night (USD)VRBO
4 Person 1 Bedroom Condo with Waterview Patio - Snapper - Welcome to our newly renovated one-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our newly renovated one-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep four g ...
From $281 per night (USD)VRBO
Click For PricingExpedia
Matlacha Home w\/ Boat Mooring & Gulf Access!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Make your next Florida vacation one to remember when you book this 2-bedroom, 1-bathroom vacation rental in Matlacha! Fe ...
Click For PricingExpedia
From $252 per night (USD)VRBO
2\/2 Home in Bokeelia, Boat Lift Included!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This two level 2 bedroom, 2 bathroom canal front home is exactly what's needed for an excellent vacation on beautiful Pi ...
From $252 per night (USD)VRBO
Click For PricingExpedia
3\/2 Beautiful Pool Home on the Water! No Hurricane Damage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
There is nothing better than slipping away to your tropical paradise vacation home knowing that everything is in tip top ...
Click For PricingExpedia
From $688 per night (USD)VRBO
🐠Waterfront Island and Pool Dream Retreat!🐋
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
🌴Unique and tranquil getaway. No hurricane damage 🐠Heated pool on the water… make your families dream vacation! 🏖Priv ...
From $688 per night (USD)VRBO
Click For PricingExpedia
Old world Florida luxury waterfront sunsets!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This luxury unit on the open waters of the Matlacha Aquatic Preserve is part of a double unit and is now ready for guest ...
Click For PricingExpedia
From $620 per night (USD)VRBO
Newly Remodeled 4 Bedroom House w Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nama-Stay is located on a barrier island in southwest Florida. In fact, the only way to get to the island by boat or pri ...
From $620 per night (USD)VRBO
From $716 per night (USD)Expedia
Special:15% Discount! Book 2025 w\/private pool, elevator, ocean view!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Turtle Cove on Upper Captiva Island is here to help you provide an experience for your loved ones. Book your stay today ...
From $716 per night (USD)Expedia
From $387 per night (USD)VRBO
Includes 3 Pools, Kayaks, Tennis, Golf Cart & Both Island Clubs! Dock Available!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on North Captiva Island, in Safety Harbor Club, this comfortable home is conveniently located near beaches, pool ...
From $387 per night (USD)VRBO
From $490 per night (USD)Expedia
A True JEWEL on the Water - includes Boat and Spa!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Jewel of the Water - this spacious home boasts 4 bedrooms, 2 of which have ensuite baths. Dock and lift with 24ft Sweet ...
From $490 per night (USD)Expedia
From $459 per night (USD)VRBO
SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SANTA CLARA BEACH HOUSE is a NEW LISTING and is a luxurious, newly furnished 3 bedroom harbor front rental property loca ...
From $459 per night (USD)VRBO
From $528 per night (USD)Expedia
8 Person 3-Bedroom Condo with Private Patio - Mermaid - Welcome to our newly renovated, luxurious and spacious three-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to our newly renovated three-bedroom condo situated on the beautiful Gulf coast! With the ability to sleep eight ...
From $528 per night (USD)Expedia
From $440 per night (USD)VRBO
8 Person 2-Bedroom Condo with Waterview Patio - Manatee - Welcome to our newly renovated, spacious and luxurious two-bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to our newly renovated two-bedroom condo with a screened patio, situated on the beautiful Gulf coast! With the a ...
From $440 per night (USD)VRBO
From $334 per night (USD)Expedia
6 Person 1-Bedroom Condo with Waterview Patio Angel's Den - 6 Person 1-Bedroom Condo with Waterview Patio Angel
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our newly renovated one-bedroom condo with a screened patio, situated on the beautiful Gulf coast! With the a ...
From $334 per night (USD)Expedia
From $243 per night (USD)VRBO
2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly renovated studio condo, situated on the beautiful Gulf coast! With the ability to sleep two guests, ...
From $243 per night (USD)VRBO
From $250 per night (USD)Expedia
4 Person 1 Bedroom Condo with Waterview Balcony Fisherman Cabin - Welcome to our stunning, newly renovated one-bedroom condo room with a balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our newly renovated one-bedroom condo, situated on the beautiful Gulf coast! With the ability to sleep four g ...
From $250 per night (USD)Expedia
From $193 per night (USD)VRBO
Pine Island Breeze\/Bokeelia 1 Bdrm 1 bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A perfect place to be as close to people or as far away as you like. Pine Island is 20 minutes to busier areas of Fort ...
From $193 per night (USD)VRBO
Click For PricingExpedia
AVAILABLE FOR EASTER! 🛏️ 4 Bedrooms 🛁 4.5 Bath Pool Home on Pine Island
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Come enjoy the island life at this tastefully decorated Ranch style pool home in Bokeelia. This property is conveniently ...
Click For PricingExpedia
From $291 per night (USD)VRBO
Amazing sunsets, Fishing from the dock, Large lanai & Pool - Villa Boa Vista - Roelens Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Boa Vista "Villa Boa Vista" is the perfect vacation spot for your next getaway. This gulf access canal home with ...
From $291 per night (USD)VRBO
From $894 per night (USD)Expedia
Spectacular Sunsets. Private multilevel designer home with heated pool and spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Multilevel Designer Home with plenty of room for family. Multiple living areas and plenty of outside areas to enjoy. T ...
From $894 per night (USD)Expedia
From $323 per night (USD)VRBO
Beautiful pool home on canal with 45-foot boat dock. 10 minutes to Gulf by boat.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pine Island is the No. 1 Tarpon fishing spot in the world. Many islands to go to for shelling, fishing, dining. After yo ...
From $323 per night (USD)VRBO
From $174 per night (USD)VRBO
Are you looking for old Florida.? Lower heart rate? No high rises\/ traffic?
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Florida style home is for guests who want to relax and unwind. It is located on a quiet street and the refreshing ...
From $174 per night (USD)VRBO
From $623 per night (USD)VRBO
OCEAN WAVES -LUXE TRUE OCEAN BEACH FRONT! AMAZING VIEWS + ISLAND CLUB AMENITIES!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE BRAND NEW "OCEAN WAVES" CALENDAR IS OPEN TO BOOK YOUR DATES TODAY! ONE OF THE BEST BEACH FRONT LOCATIONS ON NORTH ...
From $623 per night (USD)VRBO
From $162 per night (USD)VRBO
Bokeelia Charming Island House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your getaway home- a newly remodeled spacious 3 beds 2 bath house, the left side unit of a duplex. Quiet and ...
From $162 per night (USD)VRBO
From $905 per night (USD)VRBO
Butterfly Beach on North Captiva Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
"Experience Island Paradise at Butterfly Beach: Your North Captiva Oasis Escape to a world of luxury and tranquility at ...
From $905 per night (USD)VRBO
From $725 per night (USD)VRBO
Oceanfront Luxury Home with Secluded Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Sandcastle is a completely updated beachfront home that has been owned by a single family for over 40 years, and i ...
From $725 per night (USD)VRBO
From $1057 per night (USD)VRBO
Reel Laxing: Private Pool, Hammocks & Games
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Reel Laxing, your ultimate retreat on North Captiva Island. This spacious 4-bedroom home offers a blend of re ...
From $1057 per night (USD)VRBO
From $114 per night (USD)Expedia
Reopened in November 2024
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great holiday days right here in one of the best places on earth! We guarantee the most beautiful sunset ...
From $114 per night (USD)Expedia
From $132 per night (USD)VRBO
Reopened in November 2024
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $132 per night (USD)VRBO
From $132 per night (USD)Expedia
Reopened in November 2024
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $132 per night (USD)Expedia
From $130 per night (USD)VRBO
Reopened in November 2024
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $130 per night (USD)VRBO
From $111 per night (USD)VRBO
Reopened in November 2024
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $111 per night (USD)VRBO
From $136 per night (USD)VRBO
Reopened in November 2024
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $136 per night (USD)VRBO
From $176 per night (USD)Expedia
Pet-Friendly \/ Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ANGLER'S INN in Matlacha, Florida is a pet-friendly waterfront "Botel" accommodation located between Cape Coral and Pine ...
From $176 per night (USD)Expedia
From $178 per night (USD)VRBO
Closest Inn to Deep Water in St James City. Perfect for monthly rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Hook Studio". Compared ...
From $178 per night (USD)VRBO
From $186 per night (USD)VRBO
Studio on the Water. Great for monthly stays!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to Southernmost Inn on Pine Island! Come and enjoy a relaxing stay on the water in our "Rod Studio". We are loc ...
From $186 per night (USD)VRBO
From $127 per night (USD)VRBO
*** private screened area by the water ***
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio "Redfish Room" in a house with 4 apartments, open water - cozy atmosphere in an open living-sleeping area with fu ...
From $127 per night (USD)VRBO
From $111 per night (USD)Expedia
***BEST FISHING AREA NEW REFURNISHED GROUPER ROOM***
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio "Grouper Room" - comfort in the smallest space - living, sleeping, cooking - ideal for singles and couples - well ...
From $111 per night (USD)Expedia
From $132 per night (USD)VRBO
*** roomy Studio Snook Suite *** perfect for Fishermen ***
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Apartment "Snook Suite" with 4 beds - open living / sleeping area - well equipped kitchen and dining area for 4 persons ...
From $132 per night (USD)VRBO
From $148 per night (USD)Expedia
Quiet, clean & comfy 2 bed-2bath with 8000lb boat lift and large screened lanai
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cute, clean and comfy 2 bed, 2 full bath mobile home in Saint James City, Florida on a quiet canal with 8000 pound boatl ...
From $148 per night (USD)Expedia
From $409 per night (USD)VRBO
Canal-front, island paradise sleeps 9 with pools, kayaks, bikes and more!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to Island Paradise! Located on the north end of Pine Island, this stunning canal-front home is light and bright ...
From $409 per night (USD)VRBO
From $426 per night (USD)VRBO
Sandy Toes Villa - North Captiva
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sandy Toes Villa is a three bedroom, two bathroom townhome located within the Safety Harbor Club on North Captiva Island ...
From $426 per night (USD)VRBO
From $520 per night (USD)VRBO
GORGEOUS HUGE BEACH HOUZ! INCLUDES ISLAND CLUB AMENITIES\/360 VIEWS\/ 2MINS 2BEACH
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
THE FANTASTIC "COASTAL SOUL" is Being Offered at an AMAZING RATE! PLEASE SEE LAST MINUTE RATE FOR MARCH 1ST WEEK RENTAL! ...
From $520 per night (USD)VRBO
From $243 per night (USD)Expedia
2 Person Studio with Patio - Island Paradise - Welcome to our stunning, newly renovated studio condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly renovated studio condo, situated on the beautiful Gulf coast! With the ability to sleep two guests, ...
From $243 per night (USD)Expedia
From $273 per night (USD)VRBO
The Hook Oar House - Waterfront Retreat with Private Boat Lifts - 2B\/2B
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to The Hook Oar House, your perfect waterfront retreat for fishing, kayaking, and boating in St. James City, Flor ...
From $273 per night (USD)VRBO
From $137 per night (USD)VRBO
Waterfront Effeciency Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This cozy efficiency apartment attached to the "Hook Oar House" has everything you need for a comfortable and relaxing ...
From $137 per night (USD)VRBO
From $248 per night (USD)VRBO
GORGEOUS RENTAL! Paradise In Old Time Florida at \"The Dew Drop Ian\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Very secluded on a dead-end road. Fabulous Stilt Cottage where the breeze keeps you cool all day in the many open air si ...
From $248 per night (USD)VRBO
From $626 per night (USD)VRBO
AWESOME NEW POOL HOME SPRAWLING OUTDR ENTERTAINING AREA\/STEPS2 OCEAN\/2CARTS\/DOCK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
BRAND NEW GORGEOUS ISLAND HOUSE RENTAL! NOW BOOKING FOR VACATION RENTALS! TYPICALY 7 NIGHT RENTALS - WEEKENDS TO WEEKEND ...
From $626 per night (USD)VRBO
From $195 per night (USD)VRBO
Island Life at its Finest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Matlacha Isles is part of the Cape Coral-Fort Myers, Florida Metropolitan Statistical Area. Imagine waking up to tropic ...
From $195 per night (USD)VRBO
From $194 per night (USD)VRBO
Bokeelia Florida's hidden gem: waterfront condos
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Your Bokeelia Haven! Escape to our charming 2-bedroom, 3-bathroom condo, perfectly designed for a relaxing g ...
From $194 per night (USD)VRBO
From $371 per night (USD)VRBO
\"GOOD DAY SUNSHINE\" LUXE ISLAND TOWNHME\/CLUB POOL\/3 BRs w2 KINGS & DOCKAGE AVAIL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*** The FABULOUS “GOOD DAY SUNSHINE” is a LUXURY ISLAND TOWNHOME located on North Captiva Island! A Remote Barrier Islan ...
From $371 per night (USD)VRBO
From $839 per night (USD)Expedia
WHITE PELICAN WATCH- Unobstructed views, private beach, heated pool, slip
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Your Dream Unobstructed Beachfront Getaway! Experience the ultimate in island living with our stunning 4-be ...
From $839 per night (USD)Expedia