Calusa Land Trust and Nature Preserve of Pine Island Rentals
- From $417 per night (USD)
VRBO
Airstrip Ocean Oasis: Tortuga Sunset
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Tortuga Sunset – Your Caribbean Escape on North Captiva Island! Transport yourself to paradise at Tortuga Su ...
From $417 per night (USD)VRBO
- From $123 per night (USD)
Expedia
Saint James City Home w\/ Direct Water Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to Pine Island for a waterfront stay at this 3-bedroom, 2-bathroom vacation rental! The bright, comfortable inter ...
From $123 per night (USD)Expedia
- From $836 per night (USD)
VRBO
\"FLORIDAYS\" Newly Completed Private Beach House w\/ Heated Pool & Spa. 2 Carts
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Photos updated December 2023 “FLORIDAYS" Completed in 2019, this new custom-designed and crafted 4 bedroom, 4 full bath ...
From $836 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Townhome with stunning view of Matlacha Pass
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning Views….A unique town home community nestled on the island of Matlacha. This Matlacha location is literally minu ...
From $300 per night (USD)Expedia
- From $193 per night (USD)
VRBO
Beautiful, cozy, clean & fresh house on a canal with private ramp, spce to moore
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This house is located at the North of Pine Island, a tranquil, scenic, peaceful, tropical scenery. The area is renown fo ...
From $193 per night (USD)VRBO
- From $350 per night (USD)
VRBO
pool house on 2 acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island stilt house,close to lavenderlanding boat ramp,jug creek and 4 winds marina,bokeelia pier, lazy flaming and capt ...
From $350 per night (USD)VRBO
- From $328 per night (USD)
VRBO
Direct Gulf Access w\/ 60' Boat Dock \/360 Views\/ Private Heated Pool\/Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
White Sands is a luxury custom built waterfront home completed in 2022. Heated pool and direct access to the Gulf of Mex ...
From $328 per night (USD)VRBO
- From $230 per night (USD)
Expedia
Seatrout Suite Bokeelia Beachouse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Seatrout Suite Bedroom with shower, queen size bed, sitting room with futon, small complete kitchen with microwave and R ...
From $230 per night (USD)Expedia
- From $196 per night (USD)
VRBO
Snapper Room Bokeelia Beachouse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Snapper Room King size bed, small refrigerator, microwave, ROKU TV and bathroom with shower. Mini fridge Microwave TV B ...
From $196 per night (USD)VRBO
- From $235 per night (USD)
Expedia
RedFish Suite Bokeelia Beachouse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Redfish Suite Comfortable second-floor living room with plenty of seating. Complete kitchen, ROKU TV with DVD, 2 queen s ...
From $235 per night (USD)Expedia
- From $203 per night (USD)
VRBO
Snook Suite Bokeelia Beachouse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Snook Suite Comfortable second-floor living room with queen size pull out sofa. Complete kitchen with microwave, ROKU T ...
From $203 per night (USD)VRBO
- From $152 per night (USD)
Expedia
Saint James hidden gem. 3\/2 canal front home with 3 kayaks.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your gulf access waterfront paradise is waiting in quaint Saint James City. 3 Kayaks and 2 bikes for your use to explor ...
From $152 per night (USD)Expedia
- From $693 per night (USD)
VRBO
VILLA IN THE AIR - 2 Golf Carts, Private Pool, Steps to the beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Gorgeous 5 bedroom home with heated elevated pool. So much space at the poolside with sun-beds and screened outdoor liv ...
From $693 per night (USD)VRBO
- From $656 per night (USD)
Expedia
Ocean views, sleeps 10, heated pool, 2 golf carts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
4/20 to 4/27 is available and priced to book!! Featuring a private heated pool, a hot tub, ping pong, foosball, cornho ...
From $656 per night (USD)Expedia
- From $352 per night (USD)
VRBO
Matlacha Isles Oasis w\/ Gulf Access & Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
An unforgettable Matlacha Isles getaway awaits at this radiant 3-bedroom, 2.5-bathroom vacation rental. The vibrant home ...
From $352 per night (USD)VRBO
- Click For Pricing
Expedia
St James City Home on Canal w\/ Boat Davit!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you’re planning a snowbird retreat or a relaxing summer getaway, head to the canals of St James City for a stay ...
Click For PricingExpedia
- From $750 per night (USD)
VRBO
STUNNING BEACH HOME-Private Pool, Bar & Game Area. 2 Carts.\nALL YOU NEED IS FUN!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
SAME OWNERS SAME HOME DIFFERENT NAME: A WAVE FROM IT ALL HAS CHANGED TO "ALL YOU NEED IS FUN" Are you ready for the be ...
From $750 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Large home on private penninsula with water views on three sides
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Large four bedroom waterfront home built in 2008. Located on private peninsula at the end of private road with water on ...
From $321 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Pirate's Captiva-Golf Cart and HOT Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Paradise!! Golf cart included with your rental. Pirates Captiva was built in 2018, and withheld Hurricane lan ...
From $425 per night (USD)VRBO
- From $106 per night (USD)
Expedia
Charming 2 Bedroom Vacation Home w\/ Pool and Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This charming getaway is nestled perfectly along Jug Creek with pool, tennis courts and boat slip. Large enough for the ...
From $106 per night (USD)Expedia
- From $285 per night (USD)
VRBO
Bokellia Tarpon Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island life Begins here. Waterfront canal. Take Your boat to Cabbage Key Boca grande Caya costa. Tarpon Capital of the W ...
From $285 per night (USD)VRBO
- Click For Pricing
Expedia
Pet-friendly, spacious, peaceful, serene, perfect for relaxing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This lovely Pine Island villa paradise, located in Bokeelia, Florida, is at the end of a quiet cul-de-sac with loads of ...
Click For PricingExpedia
- From $450 per night (USD)
VRBO
Spectacular beach front views with a short walk to members only beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bedroom 2.5 bathroom custom built home has amazing sweeping and unobstructed views of the Gulf of Mexico with mag ...
From $450 per night (USD)VRBO
- From $164 per night (USD)
Expedia
Beautiful Water Views, Tropical Sunsets, Gulf Access - Villa Island Escape - Roelens Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Villa Island Escape ~ Your Tropical Island Getaway awaits! Easy Gulf Access, Amazing Water Views, and Famous Matlacha ...
From $164 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Gorgeous Home - Captivating Cabana! Steps to pool, short golf cart ride to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Captivating Cabana - NEW rental on secluded North Captiva Island. A short ferry ride separates you from the hustle and b ...
From $418 per night (USD)VRBO
- From $834 per night (USD)
VRBO
Luxury Beachfront Home, New Lighted Fishing Dock, Shelling, Sunrises, Renovated!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Discover a secluded and unspoiled paradise on North Captiva Island, reachable solely by ferry, private boat, or small pl ...
From $834 per night (USD)VRBO
- From $130 per night (USD)
VRBO
No Rat Race here at the Royal Flush.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hidden oasis, Secluded 1 bedroom apartment set amongst the Royal Palms and Mango Trees. Private entrance. Plenty of room ...
From $130 per night (USD)VRBO
- From $130 per night (USD)
Expedia
Pine Island Pearl, private home on spacious lot
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation home minutes from several marinas, Matlacha restaurants and shops, hiking, golf, community swimming pool and bi ...
From $130 per night (USD)Expedia
- From $347 per night (USD)
VRBO
New Listing - Beach House located steps to the beach with private pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
New Listing – Beachin' & Winin', a Beach House with Private Pool Welcome to our piece of paradise!! Centrally situated ...
From $347 per night (USD)VRBO
- From $219 per night (USD)
Expedia
Deluxe King Suite w\/Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Deluxe King Suite is the epitome of comfort and sophistication, offering a private escape with distinct features. En ...
From $219 per night (USD)Expedia
- From $176 per night (USD)
VRBO
Historic Florida \"Cracker Cottage\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
NO DAMAGE FROM HURRICANE IAN!!!!! Beautiful historic property located in quaint Bokeelia, Florida. Close to boat ramps, ...
From $176 per night (USD)VRBO
- From $580 per night (USD)
Expedia
Waterfront home with private pool, dock, patio, balconies, & bikes
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Maison de Sirens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $580 per night (USD)Expedia
- Click For Pricing
VRBO
VRCC Villa Paradisio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
website: www.vr-capecoral.com Villa Paradisio - Located less than 500 yards from the Stonis Park, Restaurants, Tennis C ...
Click For PricingVRBO
- From $333 per night (USD)
Expedia
3\/3 in St James City close to restaurants, boat ramp\/marina,2 paddle-boards
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your gulf access waterfront paradise awaits! Modern home with beautiful canal views. Kick back on the dock and relax wat ...
From $333 per night (USD)Expedia
- From $146 per night (USD)
VRBO
Private home on the canal with dock, screened pool, patio, AC, & W\/D - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Rock N' Reel Boat House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $146 per night (USD)VRBO
- Click For Pricing
Expedia
Updated, single-story cottage with great deck & large yard - 1 mile to town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Quail Trail Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For PricingExpedia
- Click For Pricing
Expedia
Serene Pine Island Getaway*Game Room*Bikes & More
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Discover Pine Island, Florida's hidden gem, in this exquisitely renovated home boasting high-end finishes. Enjo ...
Click For PricingExpedia
- From $217 per night (USD)
Expedia
Brand New! Fishing aficionado dream vacation w\/Hot Tub! -Villa The Reel It Inn - Roelens Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa The Reel It Inn Introducing a brand new vacation home that is a fishing aficionado's dream come true! This stunni ...
From $217 per night (USD)Expedia
- From $151 per night (USD)
VRBO
Marina Gardens Condo, 2\/2 with Incredible Endless Water Views! Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Marina Gardens where you find endless water views! This 2/2 condo features a full kitchen, 2 bathrooms, split ...
From $151 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
NEW LISTING! OCEAN PARADISE: BEACHFRONT, SLEEPS 12, 2 CARTS, POOL, GAMES, & FUN
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Introducing Ocean Paradise: A Luxurious Beachfront Retreat on North Captiva Island, Now Available for your next vacation ...
From $1200 per night (USD)Expedia
- From $145 per night (USD)
VRBO
The Palm Tree House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
beautiful 3 bedroom 2 bath home in a 55 plus community. Situated on 1/3 of an acre and backing onto a palm tree farm, ...
From $145 per night (USD)VRBO
- From $123 per night (USD)
Expedia
Blueberry Key, 2\/1 Overlooking canal, boat dock included minutes to open water!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Blueberry Key! This brand new 2 bedroom 1 bathroom home is just the island getaway you need. Offering a queen ...
From $123 per night (USD)Expedia
- From $472 per night (USD)
VRBO
🏝️Spring Break SALTWATER&SUNSETS🏖️Newly Remodeled🏝️Golf Cart Pool&Club Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
🏝 As soon as you step on one of the BOAT FERRIES THAT DELIVERS you to the island let your cares melt away, enjoy the lu ...
From $472 per night (USD)VRBO
- From $223 per night (USD)
VRBO
3 bedroom 2 bath pool home in quiet neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to a charming 3-bedroom, 2-bathroom canal home, offering a delightful pool and dock. This tastefully decorated re ...
From $223 per night (USD)VRBO
- Click For Pricing
VRBO
Matlacha Island House
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come experience the colorful charm and laid back style of Matlacha! This beautiful, bright and clean 2 bedroom, 2 bath ...
Click For PricingVRBO
- From $260 per night (USD)
Expedia
BEAUTIFUL WATERFRONT HOME WITH SALTWATER POOL AND BOAT LIFT
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The relaxed atmosphere at this beautiful home is perfect for vacationers who want to get away from everyday stress and w ...
From $260 per night (USD)Expedia
- Click For Pricing
Expedia
2\/1 in Bokeelia with Fenced in Yard, Minutes from Matlacha!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Bokeelia! This property is newly upgraded with amazing finishes! This two bedroom one bathroom has everything ...
Click For PricingExpedia
- From $180 per night (USD)
Expedia
Beautiful waterfront condo with gulf access
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Bocilla Island Club! Just listed and AVAILABLE JANUARY, FEB AND/OR MARCH 2024. This turnkey waterfront townho ...
From $180 per night (USD)Expedia
- Click For Pricing
Expedia
Bocilla Island Club Condo:Incredible Views of Charlotte Harbor!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy true resort style living in this beautiful condo. With some of the most lush tropical gardens on all of Pine Islan ...
Click For PricingExpedia
- From $9999 per night (USD)
Expedia
BCK N1-18
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Immaculate waterfront condo with one of the best views around. Direct access to Matlacha Pass and some of the worlds bes ...
From $9999 per night (USD)Expedia
- From $9999 per night (USD)
VRBO
Captain's Harbor Condo Relax: on your private screened balcony and enjoy the scenery just outside this gorgeous condo.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Relax on your private screened balcony and enjoy the scenery just outside this gorgeous condo. Everything you need is he ...
From $9999 per night (USD)VRBO
- From $5400 per night (USD)
Expedia
Blue Crab Key Condo! Two Bedroom Two Bathroom!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful 2 bedroom, 2.5 bath condo has everything you need to enjoy the island to the fullest! Blue Crab Key is a ...
From $5400 per night (USD)Expedia
- From $276 per night (USD)
VRBO
Bokeelia Bliss! 3\/2 with Pool & Hot Tub, Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bokeelia, Florida is home to some of the world's best fishing grounds, and it's all at your fingertips when you stay in ...
From $276 per night (USD)VRBO
- From $145 per night (USD)
Expedia
Blue Crab Key Condo with Amazing Water Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful, Bright & Airy Condo with Spectacular Views of Pine Island Creek. This beautiful 2 bedroom 2 and 1/2 bath cond ...
From $145 per night (USD)Expedia
- From $9999 per night (USD)
VRBO
Captain`s Harbor Condo: Experience real Florida living in this beautiful condo with all of its charm & beautiful artwork
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience real Florida living in this beautiful condo with all of its charm. True island decor abounds in this 2 bedroo ...
From $9999 per night (USD)VRBO
- From $360 per night (USD)
VRBO
GORGEOUS HOME WITH HEATED POOL ON WATER AND COMMUNITY BOAT RAMP
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Come and enjoy Island Time in this beautiful 3 bedroom home with an amazing heated pool. This home has a large master be ...
From $360 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Boater's Dream Nestled On a Wide Gulf Access Canal - Bokeelia Breeze
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bokeelia Breeze • Bokeelia Vacation Rental Nestled on a wide Gulf access canal, Bokeelia Breeze is every boater's dream ...
From $350 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Bokeelia Bliss! 2\/2 Pool Home with Incredible Gulf Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Bokeelia Bliss! This two bedroom two bath pool home is everything you need in a vacation rental. Walk into th ...
From $287 per night (USD)Expedia
- From $321 per night (USD)
VRBO
Beautiful waterfront home with pool\/spa, boat lift, kayaks and kayak launch!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Island home with direct access to Matlacha Pass. A 2-story property equipped with a pool and spa, high-speed internet, s ...
From $321 per night (USD)VRBO
- From $470 per night (USD)
Expedia
Private Island Luxury * Pool * Dock * Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
🏠 Exquisite interior design & curated coastal furnishings 🏖️ Stroll to beach: chairs, umbrellas, wagon provided 🛥️ Ac ...
From $470 per night (USD)Expedia
- From $182 per night (USD)
VRBO
3\/2 POOL HOME WITH ENDLESS WATER VIEWS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bedroom 2.5 bath home is the perfect spot for relaxation. Bring your boat or enjoying the two kayaks this propert ...
From $182 per night (USD)VRBO
- Click For Pricing
Expedia
Flamingo Hideaway! 3\/2 Pool Home on Water with Boat Lift!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Flamingo Hideaway! This is the perfect island vibe vacation rental! Beautiful old Florida charm with brig ...
Click For PricingExpedia
- Click For Pricing
VRBO
ISLAND COTTAGE
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
ISLAND COTTAGE LOCATED IN BOKEELIA FLORIDA. KNOWN FOR THE BEST TARPON FISHING IN THE WORLD. BLOCKS FROM THE GULF OF MEXI ...
Click For PricingVRBO
- From $280 per night (USD)
Expedia
Two-story townhouse with a sunroom, heated pool, hot tub, & tennis courts
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Pine Island Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $280 per night (USD)Expedia
- From $137 per night (USD)
VRBO
Bocilla Island Club - Newly Renovated Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Stay at Bocilla Island Club and enjoy this beautiful 2 bedroom, 2 1/2 bath, newly refurbished, clean condo. You will ap ...
From $137 per night (USD)VRBO
- From $500 per night (USD)
Expedia
High Tide Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to High Tide Retreat on beautiful North Captiva Island. No cars, just fun and beaches. We are on a small island ...
From $500 per night (USD)Expedia
- Click For Pricing
VRBO
Your own little bit of paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautifule trailer 1 bedroom plus sofa bed so you have planty of room for 4 people . A few steps to canal that leads to ...
Click For PricingVRBO
- From $125 per night (USD)
Expedia
**New** Pine Island Paradise - Saltwater Canal 2 bed\/2 bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for your own piece of island paradise? This beautifully decorated spacious 2 bedroom, 2 bathroom home in St. Jam ...
From $125 per night (USD)Expedia
- From $1600 per night (USD)
VRBO
FALL DISCOUNTS! BEAUTY AND THE BEACH- BEACHFRONT MANSION, HEATED POOL, 2 CARTS
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 17
VISIT OUR WEBSITE WWW.BEAUTYANDTHEBEACHNORTHCAPTIVA.COM BEAUTY AND THE BEACH is a 5 Bedroom with 3 Master Suites, Sleep ...
From $1600 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Secluded Island Beach Home - Starcut Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Starcut Cottage, our dream home on our favorite island. When we stayed in this home in the spring of 2022 we ...
From $425 per night (USD)Expedia
- From $350 per night (USD)
VRBO
New! Modern 3 Bed Townhome on North Captiva Island w\/Beachfront views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ahoy, land-ho! Gorgeous getaway destination ahead! Come visit La Casa Delphine: an elegant 3-bedroom waterfront haven, t ...
From $350 per night (USD)VRBO
- From $112 per night (USD)
VRBO
Lovely 1-Bedroom Vacation Home with Pool & Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Relax with the whole family at this peaceful place to stay. High speed WI-FI, completely furnished, fully equipped kitch ...
From $112 per night (USD)VRBO
- From $278 per night (USD)
VRBO
Gorgeous Private Getaway - Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Note: This property is on Pine Island. Hurricane Ian impacted the island heavily and there was damage throughout islan ...
From $278 per night (USD)VRBO
- From $566 per night (USD)
Expedia
Turtle Escape: Luxury Island Retreat with Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🍹 Outdoor Oasis: Pool, Bar, Games, TV & Shower 🐚 Beach Access: A Leisurely Stroll Away 🛥️Private Dock Available 🏠 Ch ...
From $566 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Gorgeous Four Winds Condo, Newly Renovated!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy this beautiful newly remodeled 2 bedroom 2 bath condo with an amazing marina view! Four Winds Marina has The ...
From $144 per night (USD)VRBO
- From $184 per night (USD)
VRBO
Charming 2\/2 on the Water in St. James City! Boat Lift Included!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This 2 bedroom 2 bathroom home sits on one of the deepest canals on Pine Island, and offers a boat lift. The Gulf of Mex ...
From $184 per night (USD)VRBO
- From $108 per night (USD)
VRBO
Lina`s Tropical Retreat Down
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to what we call ... Lina's Tropical Retreat Downstairs on beautiful St James City, Florida. We're located within ...
From $108 per night (USD)VRBO
- From $525 per night (USD)
VRBO
CHARMING 4 BEDROOM POOL HOME ON NORTH CAPTIVA HAS BREATHTAKING VIEWS OF THE GULF
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Consider this On Island Time your home away from home while you visit North Captiva. This fabulous property boasts 4 bed ...
From $525 per night (USD)VRBO
- From $188 per night (USD)
VRBO
Priceless Waterfront Escape in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Discover island living at our newly-remodeled waterfront escape in Matlacha on a deep water canal. This spacious two-bed ...
From $188 per night (USD)VRBO
- From $219 per night (USD)
Expedia
Off the charts Inn - Double Efficiency Room
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Experience comfort in our Double Efficiency, featuring two double beds, a living area, and a fully equipped kitchen. Unw ...
From $219 per night (USD)Expedia
- From $137 per night (USD)
VRBO
Incredible location. Waterfront unit in Matlacha with many amenities!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Turnkey furnished - 1 bed, 1 bath with additional queen pullout sofa bed in the living room. Additional outside shower. ...
From $137 per night (USD)VRBO
- From $190 per night (USD)
VRBO
2\/2 The Sea-Batical ~ Waterfront Dream Escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Keep it simple at Sea-Batical’s waterfront 2/2 with den + a bonus flex-space garage 🌴 The Sea-Batical is beautifully d ...
From $190 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Amazing Sunset Serenity Retreat at St. James City on Canal w Spa kayaks and dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our spectacular waterfront view deck with direct gulf access, along with various water-based activities with two k ...
From $239 per night (USD)VRBO
- From $993 per night (USD)
Expedia
New & Luxe ~Serene Gulf View~ 4 king suites
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Land the vacation you've always dreamed of at Isle Escape on North Captiva Island, where luxury meets tranquility in thi ...
From $993 per night (USD)Expedia
- From $130 per night (USD)
VRBO
The Island House on Pine Island\nwith heat-pump heated most privacy pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to "The Island Home", a fully equipped private retreat nestled on Pine Island. Wake up to the serene ambiance of ...
From $130 per night (USD)VRBO
- From $129 per night (USD)
Expedia
Bocilla Island Club Unit H-42
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Immerse yourself in the splendor of Charlotte Harbor with a stay in this exquisite waterfront condo. Prepare to be capti ...
From $129 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Matlacha Fishing cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This newly renovated 1940's Fishing Cottage is certain to catch your eye. Matlacha is a quiet village just on the way t ...
From $200 per night (USD)VRBO
- From $185 per night (USD)
Expedia
A piece of heaven on earth, where island time begins.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for peace and tranquility? Come visit and get to know quaint Saint James City, FL. Beautiful sunset views right ...
From $185 per night (USD)Expedia
- From $217 per night (USD)
VRBO
Beautiful three bedroom, two bath, large home has a pool and boat lift.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this stunning vacation rental, a spacious ground-level guest house with three bedrooms and two bathrooms. This ...
From $217 per night (USD)VRBO
- Click For Pricing
Expedia
St. James City POOL Home with BOATLIFT! \nEnjoy the best Florida has to offer!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wake up to the Florida Sun, sipping coffee on your screened balcony on the living level overlooking the canal and pool. ...
Click For PricingExpedia
- From $79 per night (USD)
VRBO
Island Getaway - Monthly Rental - 3 Queen Beds
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy island life in this spacious and serene space. Gulf access and restaurants are in walking distance as well as boat ...
From $79 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Turtle House in matlacha on the water with spectacular sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This peacefull yet centrally located property has all the comforts you will need for the perfect getaway or extended sta ...
From $299 per night (USD)VRBO
- From $224 per night (USD)
VRBO
Gorgeous Off Water 3\/2 with Pool in the Heart of Pine Island!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful upgraded 3 bedroom 2 bath pool home in St. James City has everything you are looking for a relaxing islan ...
From $224 per night (USD)VRBO
- From $652 per night (USD)
Expedia
Newer construction designed to bring the outside in, short walk to the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Breezy Palm is a two minute barefoot walk to the Island’s pristine white sand gulf beach. Come here to enjoy the tranqu ...
From $652 per night (USD)Expedia
- From $333 per night (USD)
VRBO
Stunning Waterfront Home with Southeast Bay Frontage - Villa Cuquita
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Cuquita • St. James City Vacation Rental Escape to your slice of paradise at Villa Cuquita, a stunning waterfront ...
From $333 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Cozy and Private our island home on North Captiva is the perfect escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled at the conclusion of a tranquil lane lies Calliope Cottage, a snug and well-appointed bungalow offering optimal ...
From $295 per night (USD)Expedia
- From $114 per night (USD)
VRBO
great vacation, water front house on pine island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a newly remodeled 2 bdr/2bth house with additional Florida room over looking water. Pine Island Tiki Bars right ar ...
From $114 per night (USD)VRBO
- From $439 per night (USD)
Expedia
Distinguished Island Home with Amazing Beach View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
🌊 Amazing beach views from most rooms in the house 🌅Stunning sunset views from crow’s nest. 🏠 Distinguished island ...
From $439 per night (USD)Expedia
- From $107 per night (USD)
VRBO
St. James City Bungalow on Canal
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to island life at this cute property on the canal! This seasonal rental includes: Washer/Dryer, Screened porch, ...
From $107 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful home 100 steps from a white sandy beach.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
If you are looking for a place to get away from it all, this is it! Enjoy beautiful quiet beaches on an island that doe ...
Click For PricingExpedia