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Osprey Vacation Rentals and Hotels

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Looking for Osprey hotels? View all hotels in the Osprey area.

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

Vacation Rentals in the Osprey/Crescent Beach area. (7 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 Osprey/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 Osprey/Englewood area. (22 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) ...


	Eagle Preserve on Lemon Bay Golf Course #2004				From $3,000/month
	3 Beds	2 Baths	Sleeps 6	House
Like new, furnished 3 bedroom, 2 bath home at the prestigious Lemon Bay Golf Course in Rotonda Florida. Eagle Preserve is nature at it's best. 2 bald eagles reside within view of the upstair's deck.. You will enjoy a quiet setting with a bird's eye view of the golf course. This home is very comfortable ...

Vacation Rentals in the Osprey/North Port area. (22 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 Osprey/Venice area. (22 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 ...


	Private Venice Island condo close to the beach #798				From $500/week
	2 Beds	1 Baths	Sleeps 6	Condo
This delightful second floor condo is just off the beach, right next to both the Venice pier and the Venice municipal airport. A short walk down the block lands you on one of the most beautiful beaches on the Gulf. Venice holds an interesting history and is untouched by developers. It contains a bit ...


	Gulf of Mexico Island home - Venice Island #797				From $650/week
	3 Beds	2 Baths	Sleeps 8	House
Drive or fly onto the island; drop your bags, grab yourself an umbrella drink, and watch the sun dissolve into the Gulf of Mexico. This Venice Island vacation home is just a short walk to the beach. Maybe you would prefer to walk to one of the best steak dinners in town or drive up the island to any ...

Vacation Rentals in the Osprey/Rotonda West area. (24 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 $950/week
	3 Beds	2 Baths	Sleeps 6	Villa
Luxury brand new Florida Villa for vacation rentals. 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. 3 bedroom 2 bathroom. master suite has direct pool access.Covered lanai. Sleeps ...


	South-facing luxury villa on golf course with pool #1295				From $924/week
	4 Beds	2 Baths	Sleeps 8	Villa
Our luxury vacation house is located in a peaceful cul-de-sac in the Rotonda region of South-West Florida. The villa is south-facing, overlooking the fairway and 15 minutes drive from beautiful Gulf of Mexico beaches. The property comfortably accommodates up to 8 people and has over 2600 sq ft of living ...


	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 ...


	House for All Seasons ..pool..hot tub..pets OK.. #484				From $750/week, $2,300/month
	3 Beds	2 Baths	Sleeps 6	House
My beautiful 3 bed, 2 bath canal front home comes with a heated pool (electric heat pump) and a hot tub on the lanai . Sleeps up to 6, Pets allowed with owner's permission. Landscaping with citrus trees and hibiscus give the tropical feeling that you are looking for. Open split floor plan includes 2 ...

Vacation Rentals in the Osprey/Boca Grande area. (32 miles away)

	An excellent location in Boca Grande, Florida #1930				From $2,500/week
	4 Beds	4.5 Baths	Sleeps 10	House
A magical blend of old and new located conveniently close to downtown Boca Grande, FL, an exclusive island resort where the pace is slow, the beaches are never crowded, and the fishing is world class. Excellent restaurants and shopping. Boca Grande appeals to every generation and this estate sized property ...


	A Dunes Of Boca #1637				From $1,500/week
	3 Beds	3 Baths	Sleeps 6	Townhouse
3 bedroom 3 bath townhouse on the Gulf of Mexico. Two pools ,Two tennis courts - miles of white sand beaches. Excellant fishing and shelling !


	A Boca Grande Beach House #1634				From $3,000/week
	5 Beds	5 Baths	Sleeps 13	House
Beautiful Boca Grande Florida Beach home - On Cul- de - sac across from the Gulf of Mexico. - Heated private pool.

Vacation Rentals in the Osprey/Treasure Island area. (44 miles away)

	A Whisper of Treasure Island - PRICE DISCOUNTED! #469				From $50/week
	1-3 Beds	1-3 Baths	Sleeps 1-8	Condo
Welcome to Whispers of Treasure Island, A Boutique condominium designated a "Superior Small Lodging". Winner of the White Glove Award For Excellence 2005 2006 You will be swept away by the unique charm of Whispers where every condominium has a different theme! We have two bedroom units ...


	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 Osprey/Madeira Beach area. (47 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 Osprey/North Fort Myers area. (51 miles away)

	RIVERFRONT/HTD POOL/EXERCISE ROOM/SAUNAS/BILLIARDS #1488				From $1,000/month
	1 Beds	2 Baths	Sleeps 1-4	Condo
A spectacular riverfront view can be seen from each room. Directly across the river from downtown Ft Myers & the famous Henry Ford & Thomas Edison Homes. Near dining, shopping, golf, theatres, sightseeing & dinner cruises, the high-speed ferry to Key West, rental boats, Sanibel & Ft Myers ...

Vacation Rentals in the Osprey/Cape Coral area. (52 miles away)

	NEWLY BUILT LAKEFRONT/HTD POOL/HOT TUB/DOCK/GARAGE #1485
	1-3 Beds	2 Baths	Sleeps 2-6	Condo
MANDALAY COVE. Large 1 to 3 bedroom/2 bath lakefront condos. Sleeps 2 to 6 people. King, queen, double, and twin beds. The condos at Mandalay Cove are beautiful lakefront Key West style condos. Near many popular SW Florida attractions. Fully furnished - linens, towels, dishes, utensils, full kitchen ...


	RIVER TOWERS/Near Gulf/Free Docks Below Lanai/Pool #1486				From $1,000/month
	2 Beds	2 Baths	Sleeps 1-6	Condo
Waterfront RIVER TOWERS is surrounded by the broad Caloosahatchee River & 2 broad canals near the Gulf of Mexico. Free docks below your screened lanai for rented or personal sail or motorboats. Fully furnished with everything needed. Elevators. Half block to Riverfront Park with walking & biking ...

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