244+ Vacation Rentals Near Pineland |
  1. USA
  2. Florida
  3. Fort Myers
  4. Pineland

Hidden Paradise Beachfront Resort - Vacation Rentals in 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

View Availability
Bokeelia BeachHouse Snapper in Bokeelia From US $260
         

New
Apartment
Bokeelia BeachHouse Snapper
  • Air Conditioner
  • Parking
  • Child Friendly

View Availability
MALU LANI Inn & Marina in Bokeelia From US $409
         

|
10.0 (6 Reviews)
Apartment
MALU LANI Inn & Marina
  • Air Conditioner
  • Parking
  • Designated Smoking Area

View Availability
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

View Availability
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

View Availability
NEW! The “WATERSIDE” COTTAGE~With dockage in Bokeelia From US $394
         

10.0 (50 Reviews)
House
NEW! The “WATERSIDE” COTTAGE~With dockage
  • Air Conditioner
  • Parking
  • Pool

View Availability
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

View Availability
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

View Availability
See More Pineland Vacation Rentals

Luxury Places to Stay in Pineland

Over 235+ 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

View Availability
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

View Availability
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

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

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

View Availability
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

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

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

View Availability
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

View Availability
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

View Availability
See More Pineland Luxury Vacation Rentals
Find More Pineland Villas, Resorts, & Rentals on BedroomVillas

Top-Rated Vacation Rentals with a Pool in Pineland

Over 107+ Top-Rated Vacation Rentals with a Pool in or Near Pineland
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

View Availability
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
  • Air Conditioner
  • Parking
  • Pool

View Availability
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

View Availability
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

View Availability
Welcome to our piece of Paradise! Great location for everything Pine Island 🎣👙🩳🚤 in Bokeelia From US $379
         

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

View Availability
Beautiful waterfront Key West style home with a pool in Bokeelia From US $391
         

10.0 (10 Reviews)
House
Beautiful waterfront Key West style home with a pool
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
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

View Availability
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

View Availability
See More Pineland Vacation Rentals with a Pool

Pet-Friendly Vacation Rentals in Pineland

Over 81+ Pet-Friendly Vacation Rentals in or Near Pineland
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

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

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

View Availability
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

View Availability
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

View Availability
Redfish suite a Welcoming 1-bedroom unit in a beach lodge right on the water in Bokeelia From US $298
         

10.0 (6 Reviews)
Apartment
Redfish suite a Welcoming 1-bedroom unit in a beach lodge right on the water
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

View Availability
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

View Availability
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

View Availability
3 Minutes to Open Water! Great Fishing Retreat on Gulf-Access Canal! Over $125 Free Daily Activities in Bokeelia From US $284
         

9.8 (79 Reviews)
House
3 Minutes to Open Water! Great Fishing Retreat on Gulf-Access Canal! Over $125 Free Daily Activities
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Pet-Friendly Vacation Rentals in Pineland on PetFriendly.io

Large Vacation Homes & Villas in Pineland

Over 7+ Large Vacation Homes & Villas in or Near Pineland
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

View Availability
PIRATES COVE Inn & Marina in Bokeelia From US $232
         

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

View Availability
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

View Availability
Osprey Lake House in Bokeelia From US $530
         

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

View Availability
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

View Availability
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
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
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

View Availability
See More Family Vacation Rentals in Pineland on FVR

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

View Availability
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

View Availability
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

View Availability
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

View Availability
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

View Availability
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

View Availability
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

View Availability
See More Properties

Pineland Vacation Rentals and Airbnb Places to Stay Under $200

Over 61+ Pineland Vacation Rentals and Airbnb Places to Stay Under $200
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

View Availability
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

View Availability
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

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

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

View Availability
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

View Availability
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

View Availability
Captain`s Harbor Condo 2/2 on the water! in Bokeelia From US $194
         

8.0 (1 Review)
Condo
Captain`s Harbor Condo 2/2 on the water!
  • Pool
  • Security/Safety
  • Internet

View Availability
2/2 Privacy in Pine Island! in Bokeelia From US $109
         

8.0 (1 Review)
House
2/2 Privacy in Pine Island!
  • Air Conditioner
  • Parking
  • TV

View Availability
See More Pineland Vacation Rental Deals

Instantly Bookable Vacation Homes in Pineland

Over 110+ Instantly Bookable Vacation Homes in or Near Pineland
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

View Availability
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

View Availability
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

View Availability
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

View Availability
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

View Availability
Beautiful waterfront condo with gulf access in Bokeelia From US $252
         

10.0 (1 Review)
Condo
Beautiful waterfront condo with gulf access
  • Air Conditioner
  • Parking
  • Pool

View Availability
Stunning canal-front home with pools, AC, W/D & hammock in Bokeelia From US $596
         

9.8 (48 Reviews)
House
Stunning canal-front home with pools, AC, W/D & hammock
  • Air Conditioner
  • Pool
  • TV

View Availability
Bokeelia Island Oasis: Waterfront, Private Dock! in Bokeelia From US $455
         

9.8 (39 Reviews)
House
Bokeelia Island Oasis: Waterfront, Private Dock!
  • Air Conditioner
  • Parking
  • Pool

View Availability
See More Pineland Short-Term Vacation Rentals

About Pineland Vacation Rentals

With more than 244 Pineland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hiddenparadisebeachfrontresort and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Pineland.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hiddenparadisebeachfrontresort 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 758.15 ft² on average, with prices averaging US $431 a night.

Hiddenparadisebeachfrontresort 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
Vacation Homes 166
Holiday Apartments 21
Cottages 9
Cabin Rentals 1
Others 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Pineland

★ Pro Tip: Hiddenparadisebeachfrontresort makes it easy to compare the best listings on Hiddenparadisebeachfrontresort homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Hiddenparadisebeachfrontresort 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

Hiddenparadisebeachfrontresort 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

What are the top vacation rentals in Pineland?

There are a lot of options in Pineland. If you plan on staying in the Pineland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pineland:

How many vacation rentals are available in Pineland?

Currently, the total number of properties listed in 2026 is over 244 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.