Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $1004 per night (USD)VRBO
Private beach access, Pool, outdoor bar!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
5 Star Property. We are located on the northern tip of North Captiva Island, with lots of privacy away from the crowds ...
From $1004 per night (USD)VRBO
From $1145 per night (USD)VRBO
Flip Flops BEACH FRONT house and Sand Bar. \nMajestic panoramic views and sunsets
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Beautiful 2 story beach front house with ground floor Patio and Sand Bar. Home is located on the exclusive North Captiva ...
From $1145 per night (USD)VRBO
From $630 per night (USD)VRBO
GORGEOUS ISLAND BEACH HOME 4 BRS\/PRIVATE POOL\/TIKI\/360 ISLAND VIEWS\/PET FRIENDLY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FANTASTIC OPPORTUNITY! GREAT RATES! BOOK NOW! Thank you for your interest in Paloma Beach House! Book us today for your ...
From $630 per night (USD)VRBO
From $988 per night (USD)VRBO
AMAZING, LUXURIOUS & TRUE OCEAN BEACH FRONT! WHOLE DUPLEX! ISLAND CLUB INCLUDED!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
THE BRAND NEW "OCEAN WAVES" Unit 3 and THE BRAND NEW "BEACH DAYZ" Unit 4 - CALENDAR JUST OPENED UP! BOOK YOUR DATES TOD ...
From $988 per night (USD)VRBO
From $424 per night (USD)VRBO
Antigua Cay Retreat is a stylish home with pool on deep water canal in Bokeelia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably right on the water in Bokeelia at this amazing 3 bedroom 2 bath fully renovated custom home. This lovel ...
From $424 per night (USD)VRBO
From $693 per night (USD)VRBO
BEACH DAYZ - LUXE TRUE OCEAN BEACH FRONT! AMAZING VIEWS + ISLAND CLUB AMENITIES!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
"BEACH DAYZ" HAS JUST OPENED UP! SPECIAL RATES FOR THIS NEWLY LISTED PROPERTY JUST LISTED ON VRBO 7/14/24! ONE OF THE B ...
From $693 per night (USD)VRBO
From $300 per night (USD)VRBO
3\/2 Pool Home on the Water in Bokeelia!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bokeelia Oasis! This charming 3 bedroom two bathroom home is located on a canal that has easy access to the gulf! Featur ...
From $300 per night (USD)VRBO
From $175 per night (USD)Expedia
2\/2 Home in Cherry Estates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come relax and soak up the great Florida weather in this cozy 2 bedroom 2 bath home with great water access to the Intra ...
From $175 per night (USD)Expedia
From $316 per night (USD)VRBO
Fishing inshore, offshore, with easy access to Charlotte Harbor and Gulf.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Quaint little cottage with three bedrooms located on the tip of Pine Island. Go boating in Charlotte Harbor with quick a ...
From $316 per night (USD)VRBO
From $264 per night (USD)Expedia
Pool home with Deep canal and direct access out to boating area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom pool home on deep Monroe Canal. Put your boat at the dock and avoid the ramp each day, fish from th ...
From $264 per night (USD)Expedia
From $244 per night (USD)VRBO
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 $244 per night (USD)VRBO
From $314 per night (USD)Expedia
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 $314 per night (USD)Expedia
From $422 per night (USD)VRBO
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 $422 per night (USD)VRBO
Click For PricingExpedia
Outstanding 3 BR waterfront pool home in Matlacha Isles\/min.to Gulf of Mexico
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully stocked, and beautifully furnished 3-bedroom 2-bathroom waterfront Villa in quaint Matlacha Isles. Pool, kayaks, f ...
Click For PricingExpedia
From $128 per night (USD)VRBO
A little piece of paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Indulge yourself in beautiful sunsets and the peaceful island life in this one bedroom, one bathroom mobile home just m ...
From $128 per night (USD)VRBO
From $231 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 $231 per night (USD)Expedia
From $1234 per night (USD)VRBO
Sunning Gulf Views! Pool and Endless Entertainment
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 9
🌅 360° Gulf-to-Bay Views 🎉 Outdoor Paradise: Pool, Bar, Dart Boards, TVs, Games, Outdoor Shower, Fat-Tire Bikes+ 🏖️St ...
From $1234 per night (USD)VRBO
From $441 per night (USD)Expedia
New Pool Coming! Charming 2\/2 Incredible Water Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This immaculate 2 bedroom 2 bathroom home is canal front with Direct Access to the Intra-coastal Waterway, your gateway ...
From $441 per night (USD)Expedia
From $260 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 $260 per night (USD)VRBO
From $235 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 $235 per night (USD)Expedia
From $247 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 $247 per night (USD)VRBO
From $299 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 $299 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 $245 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 $245 per night (USD)VRBO
From $202 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 $202 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 $371 per night (USD)VRBO
Weekly Rental in Bokeelia! Captain's Cove Community!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This 2-bedroom, 2-bathroom home in Bokeelia is an excellent choice for a seasonal rental! Situated in Captain's Cove, it ...
From $371 per night (USD)VRBO
From $312 per night (USD)Expedia
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 $312 per night (USD)Expedia
From $665 per night (USD)VRBO
Incredible 3\/2 Pool Home on Water in St. James City! No Hurricane Damage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
*No Hurricane Damage* Welcome to 'In July, a lemonade'! This 3 bedroom 2 bathroom home has been completed renovated top ...
From $665 per night (USD)VRBO
From $350 per night (USD)Expedia
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)Expedia
From $209 per night (USD)VRBO
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 $209 per night (USD)VRBO
From $260 per night (USD)Expedia
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)Expedia
From $484 per night (USD)VRBO
Matlacha Palms - Direct Gulf Access - Near Burnt Store\/Pine Island
- 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 $484 per night (USD)VRBO
From $503 per night (USD)Expedia
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 $503 per night (USD)Expedia
From $236 per night (USD)VRBO
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 $236 per night (USD)VRBO
From $218 per night (USD)Expedia
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 $218 per night (USD)Expedia
From $175 per night (USD)VRBO
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 $175 per night (USD)VRBO
From $132 per night (USD)Expedia
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)Expedia
From $676 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 $676 per night (USD)VRBO
From $900 per night (USD)Expedia
Minutes to the beach w\/private pool, elevator, ocean view!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Turtle Cove! This gorgeous home will provide multiple families with a well stocked kitchen, comfortable beds ...
From $900 per night (USD)Expedia
From $380 per night (USD)VRBO
Boat Dock & Island Clubs Included 3 pools, Kayaks, Tennis & 5 min walk to Beach
- 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 $380 per night (USD)VRBO
From $203 per night (USD)Expedia
Waterfront House near Boca Grande Pass!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Authentic fishing cottage! Waterfront house with access to world class fishing. Come via boat, trailer your boat, or cha ...
From $203 per night (USD)Expedia
From $367 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 $367 per night (USD)VRBO
From $241 per night (USD)Expedia
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 $241 per night (USD)Expedia
From $526 per night (USD)VRBO
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 $526 per night (USD)VRBO
From $835 per night (USD)Expedia
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 $835 per night (USD)Expedia
Click For PricingVRBO
2 Person Efficiency with Waterview Patio - Anchor's Inn - Welcome to our newly renovated efficiency, where comfort meets style.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly renovated one-room efficiency with a screened patio, situated on the beautiful Gulf coast. Relax in ...
Click For PricingVRBO
From $379 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 with private laundry and patio, situated on the beautiful Gulf coast! ...
From $379 per night (USD)Expedia
From $331 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 $331 per night (USD)VRBO
From $284 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 $284 per night (USD)Expedia
Click For PricingVRBO
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 PricingVRBO
From $304 per night (USD)Expedia
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 $304 per night (USD)Expedia
From $276 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 $276 per night (USD)VRBO
From $300 per night (USD)Expedia
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 ...
From $300 per night (USD)Expedia
From $996 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 $996 per night (USD)VRBO
From $172 per night (USD)VRBO
Boaters Paradise in beautiful St. James City
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bring your own boat or rent one while you stay and play. Close to the gulf with easy access by boat. Great for water re ...
From $172 per night (USD)VRBO
Click For PricingExpedia
**Fishing Cottage * Gulf Access * Romantic Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Adventure awaits. Enjoy ocean access for fishing near and around the scenic Charlotte Harbor. This cottage sit ...
Click For PricingExpedia
From $405 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 $405 per night (USD)Expedia
From $914 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 $914 per night (USD)VRBO
From $191 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 $191 per night (USD)VRBO
From $1088 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 $1088 per night (USD)VRBO
From $181 per night (USD)Expedia
Single-Story Home in Bokeelia: Pets Welcome!
- 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 $181 per night (USD)Expedia
From $218 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 $218 per night (USD)VRBO
From $1076 per night (USD)Expedia
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 $1076 per night (USD)Expedia
From $144 per night (USD)VRBO
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 $144 per night (USD)VRBO
From $249 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 $249 per night (USD)Expedia
From $437 per night (USD)VRBO
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 $437 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 $144 per night (USD)VRBO
Reopened in November 2023
- 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 $144 per night (USD)VRBO
From $151 per night (USD)Expedia
Reopened in November 2023 !!!
- 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 $151 per night (USD)Expedia
From $131 per night (USD)VRBO
Reopened in November 2023 !!!
- 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 $131 per night (USD)VRBO
From $131 per night (USD)VRBO
Reopened in November 2023!!!
- 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 $131 per night (USD)VRBO
From $243 per night (USD)VRBO
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 $243 per night (USD)VRBO
From $187 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 $187 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 $144 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 $144 per night (USD)VRBO
From $153 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 $153 per night (USD)VRBO
From $130 per night (USD)VRBO
***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 $130 per night (USD)VRBO
From $152 per night (USD)VRBO
Reopened in November 2023
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
You will enjoy great days right here in one of the best places on earth! We guarantee the most beautiful sunset of Flor ...
From $152 per night (USD)VRBO
From $145 per night (USD)VRBO
Reopened in November 2023
- 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 $145 per night (USD)VRBO
From $516 per night (USD)VRBO
GORGEOUS HUGE BEACH HOUZ! INCLUDES ISLAND CLUB AMENITIES\/360 VIEWS\/ 2MINS 2BEACH
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
OUR NEW RENATL THE FANASTIC "COASTAL SOUL" is Being Offered at an AMAZING RATE! This GORGEOUS, SPRAWLING, HIGH END Hom ...
From $516 per night (USD)VRBO
From $402 per night (USD)Expedia
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 $402 per night (USD)Expedia
From $392 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 $392 per night (USD)VRBO
From $182 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 $182 per night (USD)Expedia
From $290 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 $290 per night (USD)VRBO
From $146 per night (USD)Expedia
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 $146 per night (USD)Expedia
From $227 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 $227 per night (USD)VRBO
From $184 per night (USD)Expedia
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 $184 per night (USD)Expedia
From $191 per night (USD)VRBO
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 $191 per night (USD)VRBO
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
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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 PricingVRBO
From $769 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 $769 per night (USD)VRBO
From $190 per night (USD)VRBO
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 $190 per night (USD)VRBO
From $917 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 $917 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 $190 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 $190 per night (USD)VRBO
From $461 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 $461 per night (USD)VRBO
From $833 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 $833 per night (USD)VRBO
From $167 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 $167 per night (USD)VRBO
From $795 per night (USD)Expedia
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 $795 per night (USD)Expedia