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Luxury Home Villas - Vacation Rentals in Pineland

Luxury Island Escape @ Palm Tree Villa: Private Rooftop Deck & Saltwater Pool in Bookelia From US $385
         

10.0 (3 Reviews)
Villa
Luxury Island Escape @ Palm Tree Villa: Private Rooftop Deck & Saltwater Pool
  • Air Conditioner
  • Parking
  • Pool

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Luxury Places to Stay in Pineland

Over 245+ Luxury Places to Stay in or Near Pineland
New
House
Captain's Harbor Condo Relax: on your private screened balcony and enjoy the scenery just outside this gorgeous condo.
  • Air Conditioner
  • Parking
  • Pool

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Waterfront home on Pine Island w/pool in Bokeelia From US $943
         

New
House
Waterfront home on Pine Island w/pool
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Blue Heron * fish, boat, wine, dine, relax, repeat in Bokeelia From US $800
         

9.8 (31 Reviews)
House
Blue Heron * fish, boat, wine, dine, relax, repeat
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bokeelia Daydreamin' Incredible 4 bedroom with Pool! in Bokeelia From US $782
         

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House
Bokeelia Daydreamin' Incredible 4 bedroom with Pool!
  • Air Conditioner
  • Pool
  • TV

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Oceanfront Multi-Family Retreat . 4 Bed, 4.5 Bath . 2 Fully Equipped Kitchens in Bokeelia From US $731
         

10.0 (2 Reviews)
House
Oceanfront Multi-Family Retreat . 4 Bed, 4.5 Bath . 2 Fully Equipped Kitchens
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tarpon Tide Grand Remodeled 3 bdrm Waterfront in Bokeelia From US $670
         

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House
Tarpon Tide Grand Remodeled 3 bdrm Waterfront
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Boat House! Home with 2 Living Spaces in Bokeelia, Sleeps 11! in Bokeelia From US $658
         

10.0 (10 Reviews)
House
The Boat House! Home with 2 Living Spaces in Bokeelia, Sleeps 11!
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Barrancas Barnacle! A Private Canal-Front Island Oasis w/Dock, Sleeps 10 in Bokeelia From US $649
         

10.0 (16 Reviews)
House
The Barrancas Barnacle! A Private Canal-Front Island Oasis w/Dock, Sleeps 10
  • Air Conditioner
  • Parking
  • Pool

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Top-Rated Vacation Rentals with a Pool in Pineland

Over 111+ Top-Rated Vacation Rentals with a Pool in or Near Pineland
The Quarterdeck Cottage~Boat dockage available directly across the street in Bokeelia From US $296
         

10.0 (52 Reviews)
Cottage
The Quarterdeck Cottage~Boat dockage available directly across the street
  • Air Conditioner
  • Parking
  • Pool

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NEW! The “WATERSIDE” COTTAGE~With dockage in Bokeelia From US $396
         

10.0 (51 Reviews)
House
NEW! The “WATERSIDE” COTTAGE~With dockage
  • Air Conditioner
  • Parking
  • Pool

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Fishing inshore, offshore, with easy access to Charlotte Harbor and Gulf. in Bokeelia From US $315
         

10.0 (37 Reviews)
Cottage
Fishing inshore, offshore, with easy access to Charlotte Harbor and Gulf.
  • Air Conditioner
  • Parking
  • Pool

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Paradise awaits you at the Bocilla Island Club on Pine Island Florida. in Bokeelia From US $256
         

10.0 (33 Reviews)
Condo
Paradise awaits you at the Bocilla Island Club on Pine Island Florida.
  • Air Conditioner
  • Parking
  • Pool

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Waterfront condo located in the waterfront paradise of Bokeelia in Bokeelia From US $290
         

10.0 (16 Reviews)
Condo
Waterfront condo located in the waterfront paradise of Bokeelia
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  • Pool

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Condo w use of a 10k boat lift. 5min to open water. Tarpon capital 15min away in Bokeelia From US $228
         

10.0 (15 Reviews)
House
Condo w use of a 10k boat lift. 5min to open water. Tarpon capital 15min away
  • Air Conditioner
  • Parking
  • Pool

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Fishermen's, Golfer's, Boater's, Kayaker's, Birder's & Snowbird's Dream! in Bokeelia From US $218
         

10.0 (15 Reviews)
House
Fishermen's, Golfer's, Boater's, Kayaker's, Birder's & Snowbird's Dream!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Welcome to our piece of Paradise! Great location for everything Pine Island 🎣👙🩳🚤 in Bokeelia From US $382
         

10.0 (11 Reviews)
House
Welcome to our piece of Paradise! Great location for everything Pine Island 🎣👙🩳🚤
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  • Parking
  • Pet Friendly

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Pet-Friendly Vacation Rentals in Pineland

Over 86+ Pet-Friendly Vacation Rentals in or Near Pineland
Bokeelia Cottage w/Private Pool in Bokeelia From US $202
         

9.4 (28 Reviews)
House
Bokeelia Cottage w/Private Pool
  • Air Conditioner
  • Pet Friendly
  • Pool

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1 Mi to Boat Ramp: Bokeelia Home w/Screened Patio in Bokeelia From US $194
         

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10.0 (1 Review)
House
1 Mi to Boat Ramp: Bokeelia Home w/Screened Patio
  • Parking
  • Pet Friendly
  • Balcony/Terrace

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Prettiest Sunset View Pine Island Waterfront Home on Water Paradise w/Golf Cart in Bokeelia From US $223
         

9.4 (58 Reviews)
House
Prettiest Sunset View Pine Island Waterfront Home on Water Paradise w/Golf Cart
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful Bokeelia! Fishing dream! Bring your boat and your dog in Bokeelia From US $334
         

10.0 (30 Reviews)
Apartment
Beautiful Bokeelia! Fishing dream! Bring your boat and your dog
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Oasis with Boat Lift & Hot Tub in Bokeelia in Bokeelia From US $370
         

10.0 (17 Reviews)
House
Waterfront Oasis with Boat Lift & Hot Tub in Bokeelia
  • Air Conditioner
  • Parking
  • Pet Friendly

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3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing in Bokeelia From US $460
         

10.0 (9 Reviews)
House
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
  • Air Conditioner
  • Parking
  • Pet Friendly

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Antigua Cay Retreat is a stylish home with pool on deep water canal in Bokeelia in Bokeelia From US $363
         

10.0 (8 Reviews)
House
Antigua Cay Retreat is a stylish home with pool on deep water canal in Bokeelia
  • Air Conditioner
  • Parking
  • Pet Friendly

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Brand New Build, 3/3 Heart of Bokeelia! Boat Ramp Across the Street! in Bokeelia From US $520
         

10.0 (7 Reviews)
House
Brand New Build, 3/3 Heart of Bokeelia! Boat Ramp Across the Street!
  • Air Conditioner
  • Pet Friendly
  • TV

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Large Vacation Homes & Villas in Pineland

Over 7+ Large Vacation Homes & Villas in or Near Pineland
Boater’s Paradise! Beautiful Home on the Water with 2 Boat Lifts & Dockage Space in Bokeelia From US $415
         

9.6 (21 Reviews)
House
Boater’s Paradise! Beautiful Home on the Water with 2 Boat Lifts & Dockage Space
  • Air Conditioner
  • Parking
  • Pet Friendly

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PIRATES COVE Inn & Marina in Bokeelia From US $232
         

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8.0 (1 Review)
Apartment
PIRATES COVE Inn & Marina
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Clubhouse - Fish, Bike and Relax in this spacious Home with a Hot Tub in Bokeelia From US $420
         

9.6 (11 Reviews)
House
The Clubhouse - Fish, Bike and Relax in this spacious Home with a Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bokeelia Oasis! Heated Pool, Sleeps 12! in Bokeelia From US $430
         

8.8 (5 Reviews)
House
Bokeelia Oasis! Heated Pool, Sleeps 12!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Osprey Lake House in Bokeelia From US $530
         

10.0 (1 Review)
House
Osprey Lake House
  • Air Conditioner
  • Parking
  • Pet Friendly

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Island Life! Great Fishing - Unique 2 Home Property w/Heated Pool -Tropical Breeze Villa 1 - Roelens in Bokeelia From US $389
         

New
House
Island Life! Great Fishing - Unique 2 Home Property w/Heated Pool -Tropical Breeze Villa 1 - Roelens
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  • Parking
  • Pet Friendly

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3-bedroom pool house in charming Bokeelia with AC, WiFi. Beautiful, peaceful, in Bokeelia From US $274
         

New
House
3-bedroom pool house in charming Bokeelia with AC, WiFi. Beautiful, peaceful,
  • Air Conditioner
  • Pet Friendly
  • View

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Wheelchair Accessible Vacation Homes in Pineland

Over 7+ Wheelchair Accessible Vacation Homes in or Near Pineland
Condo in Four Winds! 2/2 Incredible Water Views! in Bokeelia From US $304
         

8.8 (10 Reviews)
Condo
Condo in Four Winds! 2/2 Incredible Water Views!
  • Air Conditioner
  • Parking
  • Pool

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Bokeelia Bliss! 3/3 Heated Pool, Boat Ramp Included! in Bokeelia From US $536
         

8.8 (5 Reviews)
House
Bokeelia Bliss! 3/3 Heated Pool, Boat Ramp Included!
  • Air Conditioner
  • Parking
  • Pool

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Best Pine Island Location In The Beautiful Bocilla Island Club Bokeelia in Bokeelia From US $160
         

4.9 (89 Reviews)
Condo
Best Pine Island Location In The Beautiful Bocilla Island Club Bokeelia
  • Air Conditioner
  • Pool
  • TV

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Pet-friendly, spacious, peaceful, serene, perfect for relaxing in Bokeelia From US $162
         

5.0 (10 Reviews)
House
Pet-friendly, spacious, peaceful, serene, perfect for relaxing
  • Air Conditioner
  • Pet Friendly
  • Pool

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Best location on Pine Island on Jug Creek in the Bocilla Island Club Unit I-49 in Bokeelia From US $180
         

4.9 (52 Reviews)
Condo
Best location on Pine Island on Jug Creek in the Bocilla Island Club Unit I-49
  • Air Conditioner
  • Pool
  • Wheelchair Accessible

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Weekly Rental in Bokeelia! Captain's Cove Community! in Bokeelia From US $195
         

New
House
Weekly Rental in Bokeelia! Captain's Cove Community!
  • Air Conditioner
  • Parking
  • TV

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Great Reviews - Lake view - Peaceful location in Bokeelia From US $250
         

9.6 (62 Reviews)
House
Great Reviews - Lake view - Peaceful location
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pineland Vacation Rentals and Airbnb Places to Stay Under $200

Over 62+ Pineland Vacation Rentals and Airbnb Places to Stay Under $200
Island Cottage-boat ramp end of street! Walk to Jug Creek Marina! in Bokeelia From US $138
         

10.0 (38 Reviews)
Cottage
Island Cottage-boat ramp end of street! Walk to Jug Creek Marina!
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning in Bokeelia From US $174
         

10.0 (1 Review)
House
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Island House on Pine Island with heat-pump heated most privacy pool in Bokeelia From US $178
         

9.8 (6 Reviews)
House
The Island House on Pine Island with heat-pump heated most privacy pool
  • Air Conditioner
  • Parking
  • Pool

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Tiki Hut Paradise 4-bedroom Bokeelia House w Golf Cart Tesla Charger Island Time in Bokeelia From US $168
         

9.4 (14 Reviews)
House
Tiki Hut Paradise 4-bedroom Bokeelia House w Golf Cart Tesla Charger Island Time
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bocilla Island Club - Newly Renovated Condo in Bokeelia From US $172
         

9.4 (8 Reviews)
Condo
Bocilla Island Club - Newly Renovated Condo
  • Air Conditioner
  • Pool
  • Security/Safety

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Bocilla Island Club H-43 in Bokeelia From US $198
         

9.0 (4 Reviews)
Condo
Bocilla Island Club H-43
  • Air Conditioner
  • Parking
  • Pool

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2 bed/2.5 bath Waterfront Condo with 2 pools and great fishing in Bokeelia From US $170
         

8.8 (6 Reviews)
Condo
2 bed/2.5 bath Waterfront Condo with 2 pools and great fishing
  • Air Conditioner
  • Parking
  • Pool

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Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida in Bokeelia From US $196
         

8.6 (4 Reviews)
Cottage
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida
  • Air Conditioner
  • Parking
  • Pet Friendly

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Instantly Bookable Vacation Homes in Pineland

Over 118+ Instantly Bookable Vacation Homes in or Near Pineland
Direct water access to Charlotte Harbor and Gulf of Mexico with no bridges. in Bokeelia From US $375
         

10.0 (34 Reviews)
House
Direct water access to Charlotte Harbor and Gulf of Mexico with no bridges.
  • Air Conditioner
  • Parking
  • TV

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Well Equipped Pet/Smoke Free Family Home - bring your boat! in Bokeelia From US $314
         

10.0 (25 Reviews)
House
Well Equipped Pet/Smoke Free Family Home - bring your boat!
  • Air Conditioner
  • Parking
  • TV

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GORGEOUS RENTAL! Paradise In Old Time Florida at "The Dew Drop Ian" in Bokeelia From US $269
         

10.0 (11 Reviews)
House
GORGEOUS RENTAL! Paradise In Old Time Florida at "The Dew Drop Ian"
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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Boater's Dream Nestled On a Wide Gulf Access Canal - Bokeelia Breeze in Bokeelia From US $592
         

10.0 (7 Reviews)
House
Boater's Dream Nestled On a Wide Gulf Access Canal - Bokeelia Breeze
  • Air Conditioner
  • Parking
  • Pool

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Waterfront condo with easy water access to world class fishing and sightseeing. in Bokeelia From US $237
         

10.0 (5 Reviews)
Condo
Waterfront condo with easy water access to world class fishing and sightseeing.
  • Air Conditioner
  • Parking
  • Pool

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2 Mi to Boat Ramp: Home in Bokeelia in Bokeelia From US $251
         

10.0 (3 Reviews)
House
2 Mi to Boat Ramp: Home in Bokeelia
  • Air Conditioner
  • Parking
  • Pet Friendly

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Angler's Luxury Waterfront in Bokeelia - Infinity Pool, Bar & Dock for Fishing in Bokeelia From US $492
         

10.0 (1 Review)
House
Angler's Luxury Waterfront in Bokeelia - Infinity Pool, Bar & Dock for Fishing
  • Air Conditioner
  • Parking
  • Pool

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Large home on private penninsula with waterfront and views on three sides. in Bokeelia From US $489
         

10.0 (1 Review)
House
Large home on private penninsula with waterfront and views on three sides.
  • Air Conditioner
  • Parking
  • TV

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About Pineland Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Luxuryhomevilla Pineland, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Pineland. Places to stay near Pineland are 3400 ft² on average, with prices averaging US $385 a night.

Luxuryhomevilla makes it easy and safe to find and compare vacation rentals in Pineland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Pineland

Type Count
Villas 1

Use these Quick Filters to Find a Vacation Rental in Pineland

★ Pro Tip: Luxuryhomevilla makes it easy to compare the best listings on Luxuryhomevilla homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxuryhomevilla homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pineland.

Weather in Pineland

View the weather forecast for Pineland before booking your Pineland Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Pineland, FL

Luxuryhomevilla offers a large selection of top attractions around Pineland. Research things to do on your vacation before you visit Pineland.


Randell Research Center Captiva Beach Sanibel Island Southern Beach Times Square Fishing Pier Fort Myers Beach Fishermen's Village Bowman's Beach Boca Grande Beach Edison and Ford Winter Estates Sanibel Island Lighthouse Bell Tower Shops Fort Myers Country Club Sanibel Island Golf Club Gasparilla Island State Park Don Pedro Island State Park San Carlos Island Bunche Beach Centennial Park Sun Splash Water Park Florida Southwestern State College

Other Places to Stay Near Pineland, FL


Alden Pines 222 Properties Randell Research Center 216 Properties

Pineland Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Pineland?

Currently, the total number of properties listed in 2026 is over 1 in the Pineland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pineland.