Boca Grande Vacation Rentals

Beautiful and relaxing waterfront condo ready for you and your family to enjoy and make fantastic memories!! Fully renovated!! The views are amazing and natural setting is absolutely beautiful!! Located directly on the Gulf of America and Intercoastal Waterway. Please note that the condo, porches and outside areas are non-smoking. Come watch for dolphins every morning from the porch as you sip your coffee, and see the pelicans dive for fish, or be on the lookout for the local manatee that swim.......

2 Bedroom Condo in Boca Grande
Sleeps 6

People who know Boca Grande, know the Historic District is the best place to stay. My house is very private but also close to the beach, shops and restaurants. Boca Grande has no traffic lights, sprawling resorts or snowbird traffic jams -- just privacy, gorgeous white sand beaches, outstanding shops and excellent restaurants (like Key West without the crowds). Golf carts and bicycles are the best way to get around Boa Grande. It is an exclusive, barrier island just north of Sanibel and Captiva .......

4 Bedroom Vacation Home in Boca Grande
Sleeps 6

Located on the west coast of Florida, this condo is part of the Boca Grande Club, which is a 62 acre private residential community located on the gorgeous shores of the Gulf of Mexico on Gasparilla Island. The unobstructed views from this unit from the second floor (elevator available) are spectacular! Enjoy a pool, impeccable beach and grounds, tennis and fitness center. The unit is nicely furnished with a king size bed in the primary bedroom and queen size pull out couch in living room. Walk i.......

1 Bedroom Condo in Boca Grande
Sleeps 4

Discover the enchanting seaside village of Boca Grande and enjoy your ideal getaway at our two-bedroom apartment. Situated just 8 minutes from the stunning Boca Grande Beach and 10 minutes from the picturesque Gasparilla Island State Park, you'll be surrounded by the natural beauty of the area.

Unwind in the outdoor pool or soak in the hot tub after a day of exploring. Stay connected with the free WiFi, and enjoy the convenience of the in-unit washer and dryer. For entertainment, challeng.......

2 Bedroom Condo in Boca Grande
Sleeps 6

(NEW TO VRBO) BEAUTIFUL first floor 2-bedroom, 2-bath unit with Bay and Gulf views. Enjoy watching sunrises from the screened-in, comfortably furnished lanai as you sip your morning coffee.

This unit features a COMMERCIAL ICE-MAKER on the lanai, fishing rod rack and quick access to the pool, hot tub, boat dock and slips (rentals available.) Inside, you’ll find a fully equipped kitchen with plenty of seating. a wine storage fridge, brew and Keurig style coffee makers and sufficient ro.......

2 Bedroom Condo in Boca Grande
Sleeps 6

In this charming town of Boca Grande, you can find our beautiful 5-bedroom getaway. Nestled just a 2-minute walk from the pristine Boca Grande Beach and a 10 min walk to the town.

As a guest, you'll be able to enjoy a refreshing dip in the private outdoor pool which backs on to nature reserve, and stay connected with the high-speed WiFi.

Indulge in the comforts of home with the fully stocked kitchen, complete with a stove, oven, refrigerator, grill, and all the necessary appliance.......

5 Bedroom Vacation Home in Boca Grande
Sleeps 10
Pet Friendly

Enjoy all that Boca Grande has to offer in this beautiful 3 BR, 2BA single family home just off the beach. Walking distance to downtown shopping and restaurants our island paradise offers a large pool, outdoor deck, grill, and lots of tranquility. Outdoor shower, wifi, walk to tennis courts and, of course, the beautiful golden beach. One bedroom has a king, one a queen, and one has bunk-beds and a twin. There is no golf cart included with the property........

3 Bedroom Vacation Home in Boca Grande
Sleeps 7

Boca Grande is a seven mile long island in the gulf of Mexico accessible by bridge. Our condominium is only 50 steps from the water, has a great view of the gulf of Mexico and non crowded beach! We have access to the 7 mile walking beach. Our condo is fully furnished with many amenities. . . beach towels, beach chairs, Smart TV in family room and TV in most rooms. Modern, light decor to welcome you to your vacation! Lots of books for your reading pleasure, too. Be sure to pack a box for.......

2 Bedroom Condo in Boca Grande
Sleeps 6

Available for short or seasonal rental is Little House: a traditional 'Old Florida' cottage with separate guest house set in the historic district of Boca Grande, on Gasparilla Island (Florida Gulf Coast). Great beaches are a stone's throw away. (Walk to the beach in under 2 minutes...walk in fact to anything you want in town in 5minutes.) There's no fast food, no chain stores, just a unique and charming slice of bygone Florida ; Florida as it was meant to be, to borrow a tagline from the Gas.......

5 Bedroom Cottage in Boca Grande
Sleeps 6
Pet Friendly

Welcome back to beautiful Boca Grande — fully restored, refreshed, and better than ever. Our top-floor Gulf-front Sea Oats condo offers sweeping beach views, peaceful privacy, and all the comforts of a newly updated coastal retreat. Guests return year after year for the quiet charm of Sea Oats, and with the island revitalized, this is the perfect time to experience Boca Grande at its very best.

This is the kind of place families quietly pass down from generation to generation. A hidden .......

2 Bedroom Condo in BOCA GRANDE
Sleeps 6

Fully furnished 2 bedroom, 2 full bath condo as close to the beach as you can get on quaint, quiet Gasparilla Island. Wake up, roll over and view the ocean from your master bedroom suite. Then enjoy your breakfast on the lanai as you gaze at the unobstructed view of the gulf of Mexico. You might see a few early beach combers, as it's never crowded. Later, enjoy that glass of wine on the lanai while soaking in the brilliant sunsets night after night, or choose to venture down to the beach just.......

2 Bedroom Condo in Boca Grande
Sleeps 6

Recently remodeled with brand new bathrooms. 4 bedrooms: 2 master suites with king beds and 2 bedrooms with queen beds. Additional blow up mattress available. Ample family room with large smart TV. Dining area seats 6 comfortably with a kitchen table for 2. Off the kitchen is a screened in porch with 6 seats and table. Party lights for night time cocktails! Upper deck is great for watching the sunset!
Internet provided. Gas grill provided.
Storage room available to store your ex.......

4 Bedroom Vacation Home in Boca Grande
Sleeps 8

PLEASE NOTE: We rent by the week-Saturday to Saturday- December 12 thru April 30. During the rest of the year we have a strict 3 night minimum.

PLEASE NOTE: While a well behaved dog is welcome, we have had to institute a strict ONE DOG policy

PLEASE NOTE: We do not discount our rates.


Enjoy the most relaxing vacation week of your life. Park your car and walk, bike, or golf cart everywhere on island!

This charming, refurbished, 2 bedroom, 2 bath cottage with cour.......

2 Bedroom Cottage in Boca Grande
Sleeps 4
Pet Friendly

Welcome to the historic Mama Dear House. This home has undergone a remarkable renovation creating an unparalleled modern 5 bedroom home, in the heart of the Boca Grande town, w/the addition of a pool. The distance from the ocean is an easy 5 minute stroll, 3 minute bike ride. (.2miles). This home comes outfitted w/pool and beach towels, 6 beach chairs & one beach umbrella for your convenience. A wet bar/coffee bar off the dining room, game room off the living room, TVs in bedrooms & living room.......

5 Bedroom Vacation Home in Boca Grande
Sleeps 10

Welcome to the Turquoise Turtle – A Beachfront Escape in Boca Grande

Discover coastal elegance at the Turquoise Turtle, a beautifully appointed 3-bedroom, 3-bath townhome perfectly situated in the serene Turtleback Colony community. With direct access to the Gulf of Mexico and a heated community pool, this retreat embodies the relaxed sophistication of Boca Grande.

The primary suite offers a king-sized bed and private balcony access, where the soothing rhythm of the waves and pas.......

3 Bedroom Vacation Home in Boca Grande
Sleeps 6

Please book this room only if you need accessibility features or if this is the only room currently available. This room is designed for guests with disabilities. This room is on the first floor and includes a roll-in shower with rails, accessible bed, lowered sink, comfort height toilet, and accessible room controls. The hotel amenities include free parking, free wifi, daily housekeeping, and an outdoor pool. Beach towels, beach loungers, and a guest laundromat are provided for an additional fe.......

1 Bedroom Vacation Home in Boca Grande
Sleeps 5

Our economy king room includes one king bed, a private bathroom with a walk in shower, a flat screen TV, free wifi, an alarm clock, a hair dryer, a small dining table with chairs, a microwave, a mini-fridge and a coffee maker. The hotel amenities include free parking, free wifi, daily housekeeping, and an outdoor pool. Beach towels, beach loungers, and a guest laundromat are provided for an additional fee........

1 Bedroom Vacation Home in Boca Grande
Sleeps 3

PLEASE NOTE: We rent by the week, Saturday to Saturday Christmas thru April. During the rest of the year we have a strict 3 night minimum.

PLEASE NOTE: While a well behaved dog is welcome, we have had to institute a strict ONE DOG policy

PLEASE NOTE: We do not discount our rates.

Watch the boats pass quietly by at idle speed from your porch directly overlooking the Boca Grande Bayou if you rent this 3 bedroom, 4 full bathroom elevated boat house. Main living area is access.......

3 Bedroom Vacation Home in Boca Grande
Sleeps 6
Pet Friendly

Welcome to Palm Paradise, your private island retreat in Boca Grande.

This immaculate three-bedroom, three-and-a-half-bath residence has been completely renovated and thoughtfully designed to offer both style and comfort. Surrounded by mature tropical landscaping, the home creates a secluded oasis while remaining just moments from the turquoise waters and pristine sands of Boca Grande.

The open-concept floor plan and meticulous attention to detail set the tone for a refined coastal.......

3 Bedroom Vacation Home in Boca Grande
Sleeps 6

Our king room includes one king bed, a private bathroom with a shower/bathtub, a flat-screen TV, free wifi, an alarm clock, a hair dryer, a small dining table with chairs, a microwave, a mini-fridge and a coffee maker. The hotel amenities include free parking, free wifi, daily housekeeping, and an outdoor pool. Beach towels, beach loungers, and a guest laundromat are provided for an additional fee........

1 Bedroom Vacation Home in Boca Grande
Sleeps 3

This Pilot Street beach house is the perfect getaway for your vacation. Three bedrooms, three full bath with a large great room and extended outdoor living space. Kitchen renovated (granite counters, new stainless appliances, bar stool seating). Dining table for up to 8. The private outdoor deck has a dining table and sitting area and grill. All new mattresses. This is a beautiful home in the premier location in Boca Grande - quiet block just steps to the beach, walk to town, climb the lig.......

3 Bedroom Vacation Home in Boca Grande
Sleeps 6

Welcome to cozy island life in this Beachfront Condo at the Boca Grande Club named #301 Dunes Chalet with 24-hour Guard-Gate Security and on-site Resort Management to serve all your needs. Never had less than a perfect review on this condo!

Featuring panoramic ocean views, endless beaches, world-class shelling, swimming pools, hot tub, kiddie pool, fishing, beachside Tiki Bar and Clubhouse Dining Room, clay tennis courts, pickleball and fitness center. Do not list children in your rese.......

1 Bedroom Condo in Boca Grande
Sleeps 4

fabulous newer home rented for three to four weeks. Dates are flexible. Two blocks from town and beach. All within walking distance. Located on the canal. Boat dock available.
no pets. Small pool on property.
we are looking for mature adults and families to rent our family home. House keeper included. forth bedroom available.


.......

4 Bedroom Vacation Home in Boca Grande
Sleeps 8

Pilot Street House
Boca Grande Beachside Retreat: 4 BR | 3.5 BA | Sleeps 8 | Private Pool | Near the Beach
Escape to a private Boca Grande retreat - Pilot Street House - with a secluded pool, four bedrooms, and easy access to the beach and historic village—an ideal island getaway for families and friends.
Welcome to the Pilot Street House
Discover a relaxed and private Boca Grande escape at the Pilot Street House, a spacious four-bedroom home surrounded by lush tropical landscaping.......

4 Bedroom Vacation Home in Boca Grande
Sleeps 8

Welcome to The Fish House — Your Boca Grande Coastal Escape
Discover timeless charm and modern comfort at this 2-bedroom, 1-bath cottage, perfectly situated in Boca Grande's historic district. Just one block from the sugar sands of the Gulf and two blocks from the heart of town, this home offers an idyllic island getaway where relaxation meets coastal elegance.
The thoughtfully designed interior creates a warm, inviting atmosphere. The primary bedroom features a queen bed dressed in soft.......

2 Bedroom Guest house in Boca Grande
Sleeps 4

Welcome to Sundown Colony, a beachfront townhome offering an extraordinary Gulf Coast escape in beautiful Boca Grande. This 2-bedroom, 2.5-bath residence combines coastal elegance, modern convenience, and the island's storied charm—creating the perfect setting for a vacation filled with relaxation and discovery.

Upon entry, you're greeted by a bright and inviting main level designed for both comfort and entertainment. The open kitchen features a breakfast bar for casual dining, sleek ca.......

2 Bedroom Condo in Boca Grande
Sleeps 4

Welcome to Coastal Chic — Your Island Oasis in Boca Grande

Discover timeless charm and refined coastal living at Coastal Chic, a 4-bedroom, 2-bath cottage perfectly situated just one block from the powder-soft sands of Boca Grande's Gulf beaches and two blocks from the historic village center. Blending comfort, luxury, and convenience, this home offers the quintessential island retreat.

The interiors exude warmth and sophistication, with an inviting sunporch that fills the home w.......

4 Bedroom Vacation Home in Boca Grande
Sleeps 8

Our queen room includes two queen beds, a private bathroom with a shower/bathtub, a flat-screen TV, free wifi, an alarm clock, a hairdryer, a small dining table with chairs, a microwave, a mini-fridge and a coffee maker. The hotel amenities include free parking, free wifi, daily housekeeping, and an outdoor pool. Beach towels, beach loungers, and a guest laundromat are provided for an additional fee........

1 Bedroom Vacation Home in Boca Grande
Sleeps 5

A few short blocks from the beach and one block from town make this rare cottage located in the Historic District of Boca Grande the perfect get-away. Situated on an over sized property, this sunny home has recently been updated (most recently with a brand new beautiful kitchen... including a gas stove, stainless steel refrigerator, farm house sink, etc.). This house has been meticulously maintained and everything inside the home is brand new, including the furniture, linens, and appliances. The.......

3 Bedroom Vacation Home in Boca Grande
Sleeps 6
Pet Friendly

Incredible location on the South end with gorgeous beachfront nonstop views of the Gulf of Mexico! This 3/2 on the corner of Belcher is right on the beach and has the most extravagant wrap around views so you can enjoy the sunset from all angles!! You have a sliding door in each bedroom with a lanai that looks right out to the Gulf. The Master bedroom features a king bed, the bathroom has a soaking tub as well as a shower and a queen bed in each guest room. The main deck is huge giving you plent.......

3 Bedroom Vacation Home in Boca Grande
Sleeps 6

Summary:
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 villa 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.

The Space:
Enter this
<.......

4 Bedroom Villa in Boca Grande
Sleeps 8
Pet Friendly

Summary:
Three bedroom, two bath retreat located a few blocks from town and the white sandy beaches of Boca Grande. Full kitchen with island and family room. A separate work space lets you work remotely. Enjoy the deck, porch, pool, and dock. Fish and crab off the dock. Bring your boat or charter one. Stroll the barrier islands and marvel at the tropical palms, flowers, and birds. Recharge and restore yourself in nature, in town. Very walkable, only a few blocks downtown to restaurants and sh.......

4 Bedroom Vacation Home in Boca Grande
Sleeps 8
Pet Friendly

This exceptionally renovated cottage is located in the beachfront colony of Sundown on exclusive Boca Grande. Take in the sunset from almost any room in this two-story home featuring two bedrooms along with two and one half bathrooms in 1,276 square feet of living space.

This end unit features indoor and outdoor living at its finest. A stunning renovated kitchen with Viking appliances gives way to an open plan living area. The cottage`s two bedrooms each feature king-sized beds and en su.......

2 Bedroom Vacation Home in Boca Grande
Sleeps 4

The “Osprey Nest” is the perfect getaway to relax. Surrounded by crystal clear turquoise waters, world class fishing, sugar sand beaches and “Old Florida” island atmosphere, you will leave feeling restored and delighted!

We love our home and welcome guests to share daybreak sunrises and fiery sunsets! Located directly off the famous Boca Grande Pass at the southern tip of the island with private unobstructed views of the Gulf and Gasparilla Island State Park/ Historic Lighthouse........

4 Bedroom Vacation Home in Boca Grande
Sleeps 7

Set yourself apart from other beach rentals in one of the only single-family rental homes, with pool, available on Boca Grande. Entirely renovated a few years ago with new appliances, flat-panel TVs, furniture, fixtures, baths, flooring, and in-ground pool, it sleeps 6 comfortably, and up to 8 including sofa bed. The property is adjacent to a tropical nature preserve, which offers privacy for your vacation, not found in condos, townhomes or even most other single-family house rentals (you’re o.......

3 Bedroom Vacation Home in Boca Grande
Sleeps 6

Boca Grande's iconic charm is beautifully reflected in this five-bedroom residence, ideally positioned across from the historic Johann Fust Library with convenient beach access just beyond the front door. Its premier location within the Historic District also places you just a short distance to boutique shops, fine dining, and the cultural heart of downtown.
Thoughtfully updated, the home blends timeless architecture with modern comfort. Two spacious primary bedrooms upstairs each feature kin.......

5 Bedroom Vacation Home in Boca Grande
Sleeps 10