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Houses for Rent in Longboat Key, FL

Average rent

$10,000

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5801 Gulf Of Mexico Dr - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

5801 Gulf Of Mexico Dr, Longboat Key, FL 34228

In-unit laundry | Outdoor space | Garage parking

4 beds

3 baths

$19,975

House for rent

Gulf-Front Haven with Stunning Beach Views

Embrace coastal living in this expansive 4-bedroom, 3-bath home boasting over 4,200 sq. ft. of elegant space. Experience natural light through walls of windows in the open living area with vaulted ceilings. The gourmet kitchen, equipped with stainless steel appliances and a curved island, showcases breathtaking Gulf views. Enjoy a private pool, generous patio, and direct beach access. The primary suite features a private balcony and spa-style bath, adding luxury to everyday life.

6980 Poinsetta Ave - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

6980 Poinsetta Ave, Longboat Key, FL 34228

In-unit laundry | High ceilings | Ceiling fan

1 bed

1 bath

$4,650

$4,250

Price drop

House for rent

Tranquil Cottage with Modern Luxuries by the Beach

Nestled in a serene fishing village, this elegant one-bedroom cottage features vaulted ceilings and a contemporary kitchen. Enjoy high-speed internet, in-unit laundry, and exclusive boat parking. With Whitney Beach just a short stroll away, this charming retreat combines island charm with modern comfort, perfect for couples seeking a peaceful seaside getaway.

640 Broadway St - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

640 Broadway St, Longboat Key, FL 34228

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$7,250

$5,500

Price drop

House for rent

Historic Coastal Retreat with Modern Luxury

Immerse in history and elegance at this fully rebuilt coastal home in Historic Longbeach Village. This turnkey 3-bedroom, 2-bath residence features vaulted ceilings, a gourmet kitchen with quartz countertops, and spa-like bathrooms. The serene backyard boasts a lily-pad pond and fire pit, while the prime location allows easy access to beaches and waterfront dining. Enjoy modern amenities along with the charm of its historic roots, perfectly suited for personal use or vacation rentals.

600 Russell St - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

600 Russell St, Longboat Key, FL 34228

In-unit laundry | Outdoor space | Walk-in closets

4 beds

2 baths

$4,500

House for rent

Renovated 4-Bedroom Home in Charming Village

This beautifully updated 4-bedroom, 2-bathroom home features new appliances, cabinetry, and flooring throughout. With 1,280 square feet, it combines modern comfort with historic charm. Lawn maintenance is included, and there's convenient in-unit laundry. Enjoy the close proximity to stunning beaches, vibrant dining, and shopping options, making this residence perfect for the Gulf Coast lifestyle.

1155 Bogey Ln #NA - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

$16,000 - 3 Bedroom 3 Bathroom House In Longboat Key With Great Amenities

1155 Bogey Ln #NA, Longboat Key, FL 34228

In-unit laundry | Outdoor space | Garage parking

3 beds

3 baths

$12,000

House for rent

Available Nov 1

Chic Waterfront Home with Pool and Spacious Deck

This stunning 3-bedroom, 3-bathroom house offers 2,045 sq ft of luxurious living in Country Club Shores. Enjoy the serene ambiance with central air, a deck, and a refreshing pool. Included utilities such as cable, internet, and water make for stress-free living. Perfect for seasonal rentals, available for select dates in late 2026 and early 2027. Embrace the ultimate Florida lifestyle in this exquisite property!

3020 Gulf Of Mexico Dr #2 - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

3020 Gulf Of Mexico Dr #2, Longboat Key, FL 34228

In-unit laundry | Outdoor space | Storage

3 beds

3 baths

$6,500

House for rent

Luxurious Coastal Retreat with Private Pool

Experience Florida living in this exquisite three-story home, fully furnished for a comfortable stay. Spanning 3,310 sq ft, this rental features ample storage, a private pool surrounded by lush landscaping, and is just a short 3-minute walk to Gulf beaches. Perfect for sun-seekers and those who appreciate a serene outdoor oasis. Ideal for a year-long lease, this property offers the perfect blend of luxury, convenience, and relaxation.

Nearby rental good for eco-living

Nearby rental good for pet owners

1581 Gulf Of Mexico Dr #307 - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

1581 Gulf Of Mexico Dr #307, Longboat Key, FL 34228

Garage parking | Swimming pool | Furnished

1 bed

2 baths

$15,000

House for rent

Available Jan 1

Coastal Luxury Retreat with Stunning Views

Experience the ultimate in coastal living in this annual rental at The Residences at The St. Regis. This furnished 1-bed, 2-bath residence spans 1,721 sq ft, showcasing soaring ceilings and breathtaking views through floor-to-ceiling sliding glass doors. The gourmet kitchen features high-end Wolf and Sub-Zero appliances, while the elegant owner’s suite includes a spacious walk-in closet and luxurious bath. Enjoy resort-style amenities including pools, spa, fitness center, and private beach access.

537 Outrigger Ln #1 - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

537 Outrigger Lane - 1

537 Outrigger Ln #1, Longboat Key, FL 34228

Garage parking | Swimming pool | Furnished

3 beds

2 baths

$7,000

House for rent

Available Mar 11

Waterfront Haven with Direct Gulf Access

Embrace the island lifestyle in this beautifully updated 2-bedroom, 2-bath home with a den, featuring a 20,000-pound boat lift and private heated pool. Perfect for boaters, the property includes hurricane-impact sliders, lush landscaping, and deeded beach access just steps away. An open-concept kitchen with a quartz island complements the upscale finishes throughout. Enjoy the convenience of being in a sought-after community, ideal for both long-term and seasonal leases. Pets welcome!

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3740 Gulf Of Mexico Dr #114 - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

3740 Gulf Of Mexico Dr #114, Longboat Key, FL 34228

In-unit laundry | Swimming pool | Furnished

1 bed

1 bath

$3,300

House for rent

Bayfront Villa with Beach Access & Modern Style

Experience breathtaking Bay and Marina views in this beautifully furnished 1-bedroom, 1-bath villa in a serene 55+ community. Renovated with a beachy vibe, the airy great room features an open layout with ample sunlight. Enjoy private deeded beach access just a short stroll away, along with a refreshing pool. The spacious bedroom includes a walk-in closet, making this maintenance-free retreat the perfect spot to embrace the Longboat Key lifestyle.

513 Gunwale Ln - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

SINGLE_FAMILY - Longboat Key, FL

513 Gunwale Ln, Longboat Key, FL 34228

In-unit laundry | Garage parking | Swimming pool

4 beds

3.5 baths

$14,750

House for rent

Luxurious Waterfront Retreat with Private Pool

Embrace beachside living in this stunning 4-bedroom, 3.5-bath luxury home. Spanning 2,292 sq ft, it offers direct access to Sarasota Bay and deeded beach access just a short stroll away. The screened patio features a family-friendly heated pool, perfect for endless summer fun. Enjoy outdoor dining beside the gas grill while watching the sunset. Located just 2 miles from St. Armand’s Circle and 4 miles from downtown Sarasota, this home blends relaxation with vibrant local attractions.

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690 Old Compass Rd - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

690 Old Compass Rd, Longboat Key, FL 34228

In-unit laundry | Outdoor space | Garage parking

3 beds

3 baths

$25,000

House for rent

Luxurious Canal-Front Oasis with Heated Pool

Experience luxury living in this beautifully renovated 3-bedroom, 3-bathroom home boasting 3,230 sq ft of space. Features include a modern kitchen with new appliances, an inviting heated pool, and a hot tub. Perfect for boating enthusiasts, it offers a brand new boat dock and lift, plus private beach access just across the street. Enjoy breathtaking views of the wide canal from the main sitting area, making it an ideal retreat for family and friends.

2254 Harbour Court Dr - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

2254 Harbour Court Dr, Longboat Key, FL 34228

In-unit laundry | Garage parking | High ceilings

3 beds

3.5 baths

$11,500

House for rent

Waterfront Paradise with Private Dock & Golf Views

Embrace the coastal lifestyle in this stunning 3-bedroom, 3.5-bath waterfront home boasting direct water access and a private dock, perfect for boating enthusiasts. Two floating jet ski docks add to the allure. Enjoy serene water and lush golf course views while being secure with hurricane-rated doors. Spread across 3,101 sq. ft., this residence captures the essence of Florida living with both luxury and tranquility.

591 Putting Green Ln - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

591 Putting Green Ln, Longboat Key, FL 34228

In-unit laundry | Garage parking | Swimming pool

5 beds

5.5 baths

$29,000

House for rent

Luxurious Waterfront Retreat with Heated Pool & Spa

Experience a luxury getaway in this stunning 5-bedroom, 5.1-bathroom home. Spanning 4,858 sq ft, this thoughtfully designed residence features state-of-the-art kitchen appliances, granite countertops, and spacious living areas. Enjoy the screened lanai overlooking the canal, or take a short stroll to the private deeded beach. Ideal for relaxation and recreation, this home is close to golf courses, boutique shopping, and outdoor activities like biking and boating.

957 Spanish Dr N - Photo 1 of 1
Age restricted

5d+ ago

House for rent in Longboat Key

Villa - LONGBOAT KEY, FL

957 Spanish Dr N, Longboat Key, FL 34228

In-unit laundry | Swimming pool | Furnished

2 beds

2 baths

$5,500

House for rent

Waterfront Villa with Stunning Bay Views

Enjoy coastal living in this newly renovated 2-bedroom, 2-bath waterfront villa that offers breathtaking full-bay views. This turnkey furnished gem features a spacious layout, perfect for a tranquil lifestyle. Steps from the Intracoastal Waterway and close to your deeded beach access, experience the best of island living. The vibrant Spanish Main Yacht Club community adds to the charm with a heated pool and clubhouse amenities, all within minutes of downtown shopping and dining.

6979 Longboat Dr S - Photo 1 of 1

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

6979 Longboat Dr S, Longboat Key, FL 34228

In-unit laundry | Swimming pool | Ceiling fan

3 beds

2 baths

$10,000

House for rent

Private Garden Oasis with Heated Pool & Chef’s Kitchen

This tropical retreat accommodates up to 9 guests, featuring a lush garden, a sparkling heated pool, and a spacious screened lanai for outdoor relaxation. The stylish chef's kitchen boasts premium appliances, including a Wolf range, and the newly updated bedrooms provide comfort with a king bed in the primary suite and fun bunk beds in the kids' room. Just a short stroll from Whitney Beach and local dining options, this home is perfect for unforgettable family getaways.

531 Birdie Ln - Photo 1 of 1
New construction

5d+ ago

House for rent in Longboat Key

Single Family Residence - LONGBOAT KEY, FL

531 Birdie Ln, Longboat Key, FL 34228

In-unit laundry | Outdoor space | Garage parking

4 beds

3.5 baths

$14,000

House for rent

Elegant Waterfront Retreat with Pool & Boat Lift

Experience luxurious living in this stunning 4-bedroom, 3.5-bathroom home, boasting breathtaking canal views and direct access to Sarasota Bay. The spacious layout includes a gourmet kitchen, a dedicated office, and a bonus room, perfect for relaxation and productivity. Enjoy your private heated pool and spa, surrounded by beautiful landscaping. This residence features an 11,000 lb boat lift, making it a true boater’s paradise, all just minutes from pristine beaches and upscale dining.

5015 Eastchester Dr - Photo 1 of 1

5d+ ago

House for rent in Sarasota

House for rent

6420 8th Street Ct W - Photo 1 of 1

5d+ ago

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6420 8th Street Ct W Bradenton, FL 34207

6420 8th Street Ct W, Bayshore Gardens, FL 34207

Outdoor space | Garage parking

4 beds

2 baths

$2,295

House for rent

Available Apr 21

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1713 Roslyn Ave - Photo 1 of 1

4d ago

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1713 Roslyn Ave Bradenton, FL 34207

1713 Roslyn Ave, Bayshore Gardens, FL 34207

Outdoor space

3 beds

1.5 baths

$2,145

House for rent

Available May 4

Listings within 10 miles
3919 Roberts Point Rd - Photo 1 of 1

4d ago

Siesta house for rent in Siesta Key

3919 Roberts Point Rd, Siesta Key, FL 34242

In-unit laundry | Outdoor space | Garage parking

4 beds

2.5 baths

$10,500

$9,975

Price drop

House for rent

2066 Roselawn St - Photo 1 of 1

5d+ ago

Townhouse for rent in Sarasota

2066 Roselawn St, Sarasota, FL 34231

In-unit laundry | Outdoor space | Garage parking

4 beds

3.5 baths

$2,995

House for rent

4237 Higel Ave - Photo 1 of 1

5d+ ago

House for rent in Sarasota

3 beds

2 baths

$6,250

House for rent

611 89th St Nw - Photo 1 of 1

5d+ ago

House for rent in Bradenton

611 89th St Nw, Bradenton, FL 34209

In-unit laundry | Swimming pool | Microwave

5 beds

4 baths

$11,000

House for rent

6311 7th Ct E - Photo 1 of 1

4d ago

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6311 7th Ct E, Bayshore Gardens, FL 34203

Walk-in closets | Ceiling fan

3 beds

2 baths

$2,290

House for rent

Available Jul 3

5103 22nd Street Ct E - Photo 1 of 1

22h ago

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5103 22nd Street Ct E Bradenton, FL 34203

5103 22nd Street Ct E, Bayshore Gardens, FL 34203

Outdoor space | Garage parking | Walk-in closets

3 beds

2 baths

$2,240

House for rent

Available May 7

Showing 1 - 25 of 25 results
Home > House Rentals in Longboat Key
Updated: May 5, 2026

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Discover houses for rent in Longboat Key, FL

🌇Available house rentals25 houses
💰Best rent deal1713 Roslyn Ave
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🍽With dishwasher
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❄️With air conditioning
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