Vacation rentals in Boca Grande

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Top-rated vacation rentals in Boca Grande

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Guest favourite

Cottage in Matlacha

4.88 out of 5 average rating, 133 reviews

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

Jul. 18 – 25

$195 CAD per night

Guest favourite

Apartment in Boca Grande

4.89 out of 5 average rating, 180 reviews

Downtown Boca Grande Efficiency Flat#3-Special Rt

We survived Ian and are ready to host you! A great efficiency, one bath flat in the heart of historic Boca Grande on the gorgeous Gasparilla Island. Located across the street from The Temp Restaurant, down the block from Hudson's Market and around the corner from Sister's Pizza. Going to the beach, no worries, it is just down the road. Rent our place through Air BnB and receive a 10% discount on golf cart and bike rentals. You’ll love my place because of the location, and the neighborhood.

Aug. 15 – 22

$248 CAD per night

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 128 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

Jul. 23 – 30

$185 CAD per night

Guest favourite

Guesthouse in Englewood

4.97 out of 5 average rating, 201 reviews

Shabby chic cottage with pool one mile from beach

This adorable shabby chic decor style studio cottage for 2 is located on one acre of old Florida landscaping. Great area for walking, biking, for exercise. Included with this home is access to a pool and large, lovely lanai, just outside the door. Head south for 7 min to historic Dearborn St or north for 3 miles to Venice. This location offers peace and tranquility combined with accessibility to endless activities nearby. 2 twins OR one King, per your preference. The pool is unheated.

Apr. 9 – 16

$212 CAD per night

Guest favourite

Condo in Englewood

5.0 out of 5 average rating, 39 reviews

Sunrise Over the Bay

Watch the sunrise on Manasota Key in Englewood Florida and dolphins & birds from your balcony. PRIVATE BEACH ACCESS directly across the street! Beach chairs, & umbrella provided for your use. Find restaurants or jet ski rentals near by. This condo has 2 bedrooms, 1 bath and a kitchen. Boat slips available upon request & availability. You must arrange off site trailer parking. A community heated pool & grills are right outside your condo. It’s time for some spring and summer fun!

Aug. 6 – 13

$212 CAD per night

Guest favourite

Guest suite in Englewood

4.98 out of 5 average rating, 180 reviews

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The rental includes use of bikes and kayaks. Kayaks are kept at 998 Oxford Dr. We are available to launch or to help you launch kayaks at a local spot. Front porch pictured is part of the main house and is use of this space is not included.

Jun. 26 – Jul. 3

$228 CAD per night

Guest favourite

Home in Captiva

5.0 out of 5 average rating, 24 reviews

Private Island Luxury * Pool * Dock * Club Access

🏠 Exquisite interior design & curated coastal furnishings 🏖️ Stroll to beach: chairs, umbrellas, wagon provided 🛥️ Shared boat dock - ask about availability. 🏊 Private pool 🍹 Screened-in pool bar 🏓 FUN! Ping pong, cornhole, PlayStation, bikes, games ✅ Fully stocked kitchen 🧴 Plush bedding, luxurious linens & bath amenities 💻 Starlink internet 🐶 Pet-friendly 🌴 Breathtaking views; luxury treehouse experience ⭐ Dedicated guest concierge to help you plan your perfect vacation

Sep. 13 – 20

$1,064 CAD per night

Guest favourite

Home in Boca Grande

4.95 out of 5 average rating, 57 reviews

Perfect Beach House Excellent Location

Perfect Beach House, Excellent Location - Quiet Street & Very Short Walk to Beach. This Pilot Street beach house is the perfect getaway for your vacation. Three bedrooms, two full bath with a large great room and extended outdoor living space. Kitchen fully renovated (granite counters, new stainless appliances, bar stool seating). All new mattresses. The premier location in Boca Grande near the beach, walk to town, shop, dine at one of the 14 restaurants with fresh local catch...

Sep. 11 – 18

$1,334 CAD per night

Guest favourite

Condo in Englewood

4.93 out of 5 average rating, 112 reviews

Immaculate Ground Floor Beach Studio on the Gulf

Please note: This complex had minimal damage, but you may see remnants of the hurricane in the complex. There is a protective tarp on the roof of my building even though there was very few tiles that blew off in the storm. There is a separate, beachside building with the same protective tarp & is getting new stucco on the west side facing the beach. You do not see the face of this building from my property as my place faces the pool. *See my pictures for more details*

May 15 – 20

$334 CAD per night

Guest favourite

Villa in Boca Grande

4.89 out of 5 average rating, 19 reviews

Yacht Watch

Watch the yachts cruise by en route to and from Miller's Dockside, while rocking on your private and serene breeze-filled balcony. Yacht Watch sleeps 8 and has 3 bedrooms and 3 bathrooms. This charming home is a quick walk or golf cart ride downtown Boca Grande for shopping and dining. It is a most idyllic and exclusive community. Very walkable area allows for viewing of local palms and birds and exotic wildlife in addition to local attractions.

Dec. 1 – 8

$1,351 CAD per night

Guest favourite

Bungalow in Englewood

4.96 out of 5 average rating, 169 reviews

TROPICAL OASIS, MINUTES FROM THE BEACH!!

This charming 2 bedroom/2 bathroom, dog friendly home in Englewood is located 2 miles away from our beautiful Manasota Beach. Call this your home away from home, as you will find a flat screen TV, Dish, free wireless internet and a gas grill, washer/dryer, and a fully equipped kitchen. Bring your boat (boat ramp is located in the neighborhood), bathing suits, beach towels and sunscreen. We have the rest ready for you.

Nov. 2 – 9

$197 CAD per night

Guest favourite

Apartment in Englewood

4.92 out of 5 average rating, 393 reviews

BEACH FRONT Unit w/Pool Sandy Toe's #4

Directly Beach front unit. Listen to the waves, walk the beach, hunt for beautiful shells and prehistoric shark teeth, take a swim in the gulf, watch the dolphins, manatees swim by. You can even try your luck at fishing from your 75 feet of private beach. Life is good! 1 of 5 units for rent, please inquire if interested in another. 3 night minimum stay.