Longboat Key Vacation Rentals | Hotels



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Longboat Key Vacation Rentals and Hotels

Longboat Key, an eleven mile barrier island off the coast of Florida, has two championship golf courses, tennis courts, swimming, health spas, bike riding, rollerblading, and watersports like windsurfing, jetskiing, boating, fishing, SCUBA diving, snorkeling, and waterskiing. The beautiful beaches provide the perfect backdrop, whether you seek relaxation or invigoration.

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We have over 600 properties in the Longboat Key, Florida area.
Please browse our top 30 properties below

Vacation Rentals in the Longboat Key/Sarasota area. (12 miles away)

	Sarasota 60s Modern Vacation Rental Home #400				From $2,750/month
	2 Beds	2 Baths	Sleeps 4	House
An unique property located in a desirable, centrally located, Sarasota residential neighborhood. The house is a 60's modern Sarasota ranch, decorated in period designer furniture and 60s kitsch. (Danish Modern, George Nelson, Knoll, Herman Miller, and a collection of tikis and vintage barware and dishes) ...


	VACATION RENTALS 1 BLOCK FROM BEACH IN SARASOTA #393
	1 Beds	1 Baths	Sleeps 4	Hotels
Delightful studio apartments to 3 bedroom apartments tucked away on exciting Lido Key. Nestled amid a tropical garden, the units are steps from the beautiful white sands of Lido beach, with the turquoise waters of the Gulf of Mexico just beyond. Quiet side roads and boulevards are perfect for a morning ...

Vacation Rentals in the Longboat Key/Crescent Beach area. (13 miles away)

	North Florida Vacation Rental Bungalow #204				From $400/week
	2 Beds	1 Baths	Sleeps 5	House
An ideal vacation rental in St. Augustine. Fun in the sun, Florida style! Come relax on Crescent Beach in our Cottage or Bungalow, situated on Anastasia Island, just south of Historic St. Augustine. Water, water, everywhere! You are just steps away out the front door to Crescent Beach and spectacular ...


	Crescent Beach Florida Vacation Rental #203				From $500/week
	2 Beds	2 Baths	Sleeps 6	Cottage
An ideal vacation rental in St. Augustine. Fun in the sun, Florida style! Come relax on Crescent Beach in our Cottage or Bungalow, situated on Anastasia Island, just south of Historic St. Augustine. Water, water, everywhere! You are just steps away out the front door to Crescent Beach and spectacular ...

Vacation Rentals in the Longboat Key/Treasure Island area. (24 miles away)

	Affordable Beach Condos - PRICE DISCOUNTED! #469				From $100/week
	1-3 Beds	1-3 Baths	Sleeps 1-8	Condo
Welcome to Affordable Beach Condos of Treasure Island, a Themed Vacation Condominium Rental. Each Condominium has a unique theme! Choose from a 1 or 2 bedroom vacation condominium rental or a 3 bedroom Executive House. Affordable Beach Condos Boutique Condominium was designated a "Superior Small ...


	Sunset House: Waterfront Caribbean Vacation Home #248				From $135/night, $795/week, $1,795/month
	1 Beds	1.5 Baths	Sleeps 2	House
Vacation on Florida's beautiful, Gulf Coast. Drop your anchor at Sunset House, a charming waterfront home with a tranquil waterfront patio and dock on desirable Sunset Beach, Treasure Island. Located directly on the inner-coastal within 200 feet of the white sand beaches of the Gulf of Mexico and its ...

Vacation Rentals in the Longboat Key/Madeira Beach area. (27 miles away)

	Jan's Beach Dream Luxury Gulf Front Penthouse Cond #1562				From $1,050/week
	3 Beds	2 Baths	Sleeps 10	Condo
Our luxury Gulf front penthouse is located on the most southern end of Madeira Beach, Florida which is directly on John's Pass. Our three bedroom, two bath, luxury penthouse condo features walk-in closets, a fully equipped kitchen, breakfast bar, dining room and a large balcony overlooking the fabulous ...

Vacation Rentals in the Longboat Key/Indian Shores area. (34 miles away)

	BEACH LOVERS CONDO at HOLIDAY VILLAS III #2388				From $600/week
	2 Beds	2 Baths	Sleeps 8	Condo
Completely renovated: Condo completed updated and freshly painted with new everything. New ceramic tile and carpet throughout. Most recent guests rate this unit as an A+: We dare you to compare with any other units at HOLIDAY VILLAS III. New Kitchen: New cabinets, granite countertops with stainless ...


	My Indian Shores Beach Resort Vacation Condo #1484				From $625/week
	2 Beds	2 Baths	Sleeps 4-7	Condo
Magnificent 2-bedroom/2-bathroom condominium beach vacation rental in resort oceanfront property on Indian Shores Beach on the Gulf of Mexico. Indian Shores is a unique, relaxed gulf coast community located 20 miles west of Tampa in the middle of an island with Clearwater to the north and St. Petersburg ...


	My Indian Shores Vacation Condo #1124				From $562/week
	2 Beds	2 Baths	Sleeps 1-6	Condo
Magnificent Gulf Front 2-bedroom/2-bathroom resort condominium rental on the Gulf of Mexico in the relaxed beachfront town of Indian Shores. Surrounded by warm, gentle surf and plenty to do...or do nothing but savor the relaxed atmosphere and walk barefoot on the beautiful soft, white sandy beach right ...


	Beautiful Direct Beach Front Condo #1548				From $795/week
	2 Beds	2 Baths	Sleeps 6	Condo
OUR FLORIDA GETAWAY....white, sugar-soft sands...warm waters perfect for swimming...splend sunset views over the Gulf of Mexico....dolphin, seashells, bird life, and game fish...fascinating restaurants and shops just minutes away.....here memories are made. We invite you to relax by our large heated ...


	Bayshores Yacht & Tennis Club #1592				From $400/week
	2 Beds	2 Baths	Sleeps 1-4	Condo
Vacation where you can enjoy the sun, surf & tropical sunsets. This privately owned condominium sits directly on the Intercoastal Waterway just steps away to a public beach and the beautiful Gulf of Mexico! Located in the quaint beach community of Indian Shores you can enjoy golf, shelling, tennis, ...

Vacation Rentals in the Longboat Key/Indian Rocks Beach area. (36 miles away)

	Original Gulf Coast cottage in Indian Rocks Beach #341				From $800/week
	2 Beds	1 Baths	Sleeps 6	Cottage
This cottage is one of the oldest original cottages in Indian Rocks Beach. "Manning Hammock" has been lovingly refurbished and has all amenities. Built by Captain John Manning in 1926, it is nestled in a hammock of live oaks and palm trees just a block from the beach, and the intercoastal waterway. ...


	BobsFloridaBeachCondo.com Beach,HeatedPool,Tennis #2701				From $846/week
	3 Beds	2 Baths	Sleeps 6-8	Condo
Beachfront luxury condo in Indian Rocks Beach, FL (between Clearwater and Tampa/St. Petersburg) on the Gulf of Mexico available for vacation rentals, holidays, golfing adventures, romantic getaways, weddings, graduations, and corporate housing. Indian Rocks Beach is a great family beach with lots of ...


	BobsFloridaBeachCondo.com Beach,HeatedPool,Tennis #2555				From $846/week
	3 Beds	2 Baths	Sleeps 6-8	Condo
Beachfront luxury condo in Indian Rocks Beach, FL (between Clearwater and Tampa/St. Petersburg) on the Gulf of Mexico available for vacation rentals, holidays, golfing adventures, romantic getaways, weddings, graduations, and corporate housing. Indian Rocks Beach is a great family beach with lots of ...


	Chic a si Cottage, directly on Indian Rocks Beach #1341				From $1,500/week
	3 Beds	2 Baths	Sleeps 6	Cottage
Enjoy the privacy of your very own cottage directly on the white sand beaches of the Gulf of Mexico. Located on a quaint, historic barrier island, Chic a si Cottage is an Indian Rocks Beach original. Built of cypress, with vaulted ceilings, it maintains its charm with its gingerbread trim and tin roof. ...


	Gulf of Mexico - fully furnished Beachfront Condo #563				From $900/week
	2 Beds	2 Baths	Sleeps 1-4	Condo
This newly renovated, fully furnished Gulf condo, is located on a quiet white sandy beach between Clearwater and St. Petersburg. The living room and master bedroom open onto the balcony where you can enjoy morning, noon and evening views of the Gulf and beach. There is a queen size bed in the master ...

Vacation Rentals in the Longboat Key/North Port area. (41 miles away)

	Luxury Presidental Hideaway in North Port #1608				From $750/week
	3 Beds	2 Baths	Sleeps 6	Villa
North Port, fit for a King, extreem luxury. Port Charlotte, Venice area, South West Gulf Coast. Very private electric heated Pool. 3 Bedroom , 2 Bath. Spacious Accomodation. Nestelt in lush tropical area. Only 5 minutes to Interstate 75 and US 41 a 10 mile long shopping strip.


	s/w Gulf Coast - Magnificent Sub Tropical Area. #1550				From $550/week
	3 Beds	2 Baths	Sleeps 6	House
Located on the s/w Gulf Coast in a very quiet street of North Port . The Villa is embedet in a sub tropical area with lush green grass, bushes and palm trees. It is 6 min. to Interstate 75 and 5 min. to shopping, restaurants and beaches. Disney 2 1/2 hrs.Fort Meyers Airport 40 min. Fauntain of Youth ...

Vacation Rentals in the Longboat Key/Venice area. (41 miles away)

	Baycrest II Venice Florida Home #1679				From $795/week
	3 Beds	2 Baths	Sleeps 10	House
Just Listed! Available for Spring Break March 4-25 & Apr 1-30. Relax in a heated private pool that has a partial view of Roberts Bay. This wonderful 3 bedroom, 2 bathroom house is located at 424 Baycrest Drive! In fact, from our back yard you can sip a cup of coffee and watch boats sail along the ...


	Beachfront 1 & 2 Bedroom Vacation Rental Condos #1638				From $580/week
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
Beachfront, Venice Florida, Gulf Coast, beautiful, one & two-bedroom, full furnished, ranch style, condominium units with attached lanai (florida room) are available for your vacation rental of a lifetime. Located directly on the beach on the Island of Venice, Florida. All accommodations include: ...


	Lovely home for timeshare-enjoy a week in paradise #1594				From $5,000/week
	2 Beds	2 Baths	Sleeps 6	House
Excellent TIMESHARE available in PARADISE!!! Fully furnished!!! You will be close to beaches, dining, shopping , great golf and much, much more. Amenities include : Waterfront home, Three sparkling swimming pools, Whirlpool Spa, Shuffleboard, Tennis, Volleyball, Picnic area, Biking and Walking trails, ...


	Lovely 2 Bedroom House in Venice Florida #279				From $1,200/month
	2 Beds	2 Baths	Sleeps 4	House
Venice is located just 20 miles south of Sarasota airport and only 1 hour north of Fort Myers airport. It is a beautiful city, enhanced by red-tiled rooftops! Bay Indies is a very vibrant, extremely active, "55 + years young" community with 1,300 private homes, offering every activity you ...

Vacation Rentals in the Longboat Key/Dunedin area. (42 miles away)

	Florida Gulf Coast Bed & Breakfast Inn #214				From $155/night
	1 Beds	1 Baths	Sleeps 1-2	Bed and Breakfast
The Meranova Guest Inn offers luxury accommodations in a stylish, contemporary bed and breakfast setting, and is located in the charming quaint village of Dunedin. Fully renovated in 1998-1999, each distinctively different suite offers a private entrance, most with a porch or balcony, private bath, and ...

Vacation Rentals in the Longboat Key/Englewood area. (42 miles away)

	Tranquility, A Stunning Villa in Paradise #2346
	4 Beds	3 Baths	Sleeps 8	Villa
Pine Valley is located within the Rotonda on the South West coast of Florida in Charlotte County, often referred to as Florida's hidden secret, or the real Florida. It is near the beachside town of Englewood on the Gulf of Mexico. The International Airports of Tampa (1.5 hours) and Fort Myers (1 hour) ...

Vacation Rentals in the Longboat Key/Rotonda West area. (44 miles away)

	Whispering Palms on Florida's Gulf Coast #1911				From $950/week
	3 Beds	2 Baths	Sleeps 6	Villa
Our stunning home is now available for guests & is situated in the desirable & highly sought after residential community of Rotonda West, Port Charlotte, on Florida's Gulf Coast. Port Charlotte has been voted 'Best Place to live in the South' by 'Money Magazine' several times, and one of the ...


	Families Welcome-2Masters,Htd.Pool, WIFI, Golf Pkg #1863				From $900/week
	4 Beds	4 Baths	Sleeps 8	Villa
Look no further, Your Rotonda Villa awaits your arrival! Rotonda West is a gorgeous, quiet neighborhood of fine home with 6 golf courses within its boundaries. Ideally situated between Sarasota and Ft. Myers its location is the perfect place for your vacation. Close to beaches, shopping, world class ...


	SunHaven Luxury Gulf Vacation Villa #2421				From $800/week
	3 Beds	2 Baths	Sleeps 6	Villa
Luxury brand new Florida Villa for vacation rental. Built and furnished to the highest standards. Contemporary design. Private secluded heated south facing pool. Not over looked. Set in pine wooded area, quiet and peaceful. Close to Gulf beaches and crystal clear water. Ideal for beach goers, sun worshipers, ...


	ALMOST LIKE HEAVEN pool hot tub golf course PetsOK #486				From $700/week, $2,200/month
	2 Beds	2 Baths	Sleeps 6	House
This home is overlooking the third green, at the end of a dead end street, newly renovated, and pet friendly. The dining area, kitchen and family room with 2 sliders look out to the pool and lanai. The heated pool (electric heat pump) is sunny all day and the 2 level caged lanai with hot tub is shady.. ...


	SLICE OF HEAVEN pool hot tub golf course pets OK #485				From $700/week, $2,200/month
	2 Beds	2 Baths	Sleeps 6	House
You will love this 2 bed 2 bath home, overlooking the golf course. Spend your time on the oversized screened lanai, enjoying your heated (electric heat pump) pool and hot tub. This home is perfect for entertaining or spending a quiet day alone! The well equipped kitchen is open to the family room and ...

We have over 600 properties in the Longboat Key, Florida area.
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Longboat Key Vacation Rentals | Hotels