Homestead Listings

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Monthly Rent $3500

A 2 beds/1 bath vacation home located in a safe and quiet neighborhood surrounded by farmland perfect for snowbirds. Homestead, Florida, Listing ID: 26445

Located in a quiet neighborhood surrounded by farmland, gateway to the Keys, with just over 1,000 square feet of living space, this 2 beds/1 bath cozy single home built on 1.2 acre land, fully fenced-in with private driveway and parking lot. Amenities include a fully...

  • Home
  • 1100
  •  2
  •  1

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Monthly Rent $1300 - $2200

Waterfront Getaway , southern end of Pine Island. St James City, Florida, Listing ID: 22915

THIS HOME IS CURRENTLY LISTED FOR SALE. SEASONAL RESERVATIONS WILL NOT BE ACCEPTED UNTIL FALL 2018 ( PLEASE CHECK BACK FOR AVAILIBILITY). Unique one bedroom one bath canal front home. Stilt home with living area on second floor. Four hundred square foot Florida room with view...

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  • 1000-1200
  •  1
  •  1
Monthly Rent $1800 - $2550

Sorry we are booked Fort Myers, Florida, Listing ID: 23278

Cottage Delice I is the perfect couples get-a-way. It is located one mile from Bunche Beach and just one mile from San Carlos Blvd which leads over the Mantanzas pass bridge to Fort Myers Beach and just two miles to the Sanibel Island causeway leading to all that Sanibel Island...

  • RV Lot
  • 600-800
  •  1
  •  1
Monthly Rent $2400

Completely redone, immaculate bayside condo in the beautiful Florida Keys. Offered at the lowest monthly rate in the upper Keys! Tavernier, Florida, Listing ID: 23702

This is a completely redone, immaculate two-story condo in a 35-unit complex. It has two king size tempurpedic beds upstairs, and two queen size futons downstairs. There are flat screen TVs in the living rooms and bedrooms, and wireless access. The unit is located in a direct...

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  • 800-1000
  •  2
  •  1 1/2

FOR RENT Lake Worth, Florida, Listing ID: 23787

SHARE HOME WITH OWNER 15 MIN TO OCEAN WALKING DISTANCE TO TOWN 15 MIN TO WEST PALM BEACH AIRPORT TRI MIAMI RAIL SERVICE AVAILABLE BUS SERVICE AVAILABLE OWNER WILL DRIVE YOU PAY FOR GAS WITHIN REASONABLE DISTANCE AVAILABLE FOR JAN, FEB. MARCH AND APRIL 2017

  • Home
  • 1000-1200
  •  3
  •  1
Monthly Rent $5500 - $7500

Great Private Home with Spectacular Views of the Ocean from anywhere in Home!!!! Islamorada, Florida, Listing ID: 24289

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room...

  • Home
  • 1200-1400
  •  3
  •  3
Monthly Rent $3675 - $4750

"Meticulously" cared for Home the owners are now offering to share for your Vac! Islamorada, Florida, Listing ID: 24293

MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 4-6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering...

  • Home
  • 1000-1200
  •  2
  •  2
Monthly Rent $2875 - $3725

Bayfront townhouse located in the lush tropical setting of Rock Harbor Club. Key Largo, Florida, Listing ID: 24303

MINIMUM STAY: 28 Nights. Bayfront townhouse located in the lush tropical setting of Rock Harbor Club in Key Largo. You'll love the open water views from the two oversized screened balconies - one off the main living area and the other off the master suite. There's something...

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  • 1000-1200
  •  2
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Monthly Rent $3800 - $4850

3 BR Townhouse Oceanside with 30' Dock and Boat Lift Key Largo, Florida, Listing ID: 24304

Minimum Rental: 1 MONTH This is a gorgeous 3 bedroom townhouse in a private upscale ocean front condominium community! Everything you could want is located within the community - heated pool; hot tub; covered seating area; tennis court; children's playground;...

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  • 2261
  •  3
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Monthly Rent $4950

Stay in the Florida Keys! You will love this wonderful 2013 built stilt home!!!! Plantation Key, Florida, Listing ID: 24310

MINIMUM STAY: 30 DAYS NEW HOME (2013) Spend the fall or winter in the Florida Keys! You will love this wonderful 2013 built stilt home. Features include an open living area with gourmet kitchen, stainless steel appliances, including a wine refrigerator and granite...

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  • 1400-1600
  •  3
  •  2
Monthly Rent $5950 - $7950

The Florida Keys at its best.3 Bedrooms and 2 Plantation Key, Florida, Listing ID: 24311

MINIMUM STAY: 28 DAYS NEW OPPORTUNITY to LIVE THE LIFE! This 3 Bedrooms and 2

  • Home
  • 2000-2500
  •  3
  •  2 1/2
Monthly Rent $8500 - $9950

!Exceptional Home Designed for Tropical Living Pool Boat Dock Tropical Setting!! Key Largo, Florida, Listing ID: 24316

MINIMUM STAY: 1 MONTH Exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. Open concept living area on the middle level of the home offers a formal dining with 8 chairs and 3 bar stools at the kitchen counter....

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  • 2000-2500
  •  4
  •  4
Monthly Rent $2200

KEY WEST STYLE CONDO 2/2 RECENTLY UPDATED! Fort Myers, Florida, Listing ID: 24932

"THIS IS A GREAT 2/2 SECOND FLOOR CONDO WITH FRONT SCREENED LANAI AND A REAR SCREENED LANAI" - Beautifully decorated and updated condo. Key West Style in a quiet complex with tropical grounds. Located across the road from the Caloosahatchee River and across the "FREE BRIDGE" ...

  • Condo
  • 1000-1200
  •  2
  •  2
Monthly Rent $2500

cozy 2 bedroom 2 bath canal front home on a corner 3 lot sight direct access St.James City, Florida, Listing ID: 24950

100 feet of deep water access to Pine Island Sound and the Gulf of Mexico, Private 3 corner lot site with dock, covered parking, close to many local restaurants, boat & kayak rentals available nearby, All linens, dishes and cookware, washer and dryer, plenty of space to park...

  • Home
  • 1000-1200
  •  2
  •  2
Monthly Rent $6500 - $7500

THE GORGEOUS POOL, HOT TUB, and TIKI BAR are ready and waiting SENSATIONAL HOME Plantation Key, Florida, Listing ID: 25068

*****SUMMER SPECIAL ***** RECEIVE A $100 VISA GIFT CARD FOR ALL BOOKINGS BETWEEN JUNE 1, 2018 AND AUGUST 31, 2018. RESERVATION MUST BE MADE BY JUNE 30, 2018. MINIMUM STAY: 29 DAYS Sensational remodeled single family home on Plantation Key awaits your arrival. The...

  • Home
  • 1800-2000
  •  4
  •  3
Monthly Rent $1000 - $2700

2BR/2BA with golf and water view North Fort Myers, Florida, Listing ID: 25133

BEAUTIFUL 2BR/2BA MANUFACTURED HOME IN A GATED COUNTRY CLUB COMMUNITY

  • Home
  • 1000-1200
  •  2
  •  2
Monthly Rent $1800 - $3000

NEW on the Market! If You Lost Your Reservation Due to IRMA we have YOUR Replacement! Fort Myers, Florida, Listing ID: 25443

This property is strategically placed 4 miles to Fort Myers Beach's Times Square and 6 miles to Lighthouse Point of Sanibel Island. The beaches of Sanibel and Captiva have been rated as some of the best in Florida and the world. Cottage Delice III is almost 1200 square feet and...

  • RV Lot
  • 1176
  •  2
  •  2
Monthly Rent $2500 - $6300

Cute dog-friendly tropical condo close to attractions w/a pristine shared pool Key West, Florida, Listing ID: 26085

This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh...

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  • 731
  •  10
  •  1 1/2
Monthly Rent $2600 - $6300

Breezy Florida home with shared swimming pool, dog-friendly - walk to beach! Key West, Florida, Listing ID: 26094

Small families and close groups of friends will love this dog-friendly home for four in Key West! A shared swimming pool and nearby beach access provide everything you need for a great vacation. Your new home away from home rests comfortably by the city's Old Town, where lots...

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  • 694
  •  2
  •  2
Monthly Rent $3700 - $10000

Vibrant home w/hot tub & private pool blocks from the beach - dog-friendly! Key West, Florida, Listing ID: 26096

This colorful dog-friendly Florida home has everything you need for an unforgettable vacation, with a private swimming pool and hot tub and walking distance from the beach. Your home sits only a few blocks away from the soft sands and warm waters of Higgs Beach. If you'd...

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  • 2328
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Monthly Rent $3400 - $6700

Sprawling condo w/ ocean views, dock, & shared pool - dog-friendly! Key West, Florida, Listing ID: 26100

Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views, and more await you. Nestled on the northern side of Key West, you have easy access to the shops and restaurants of Old Town, as well as a dock and...

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  • 1237
  •  2
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Monthly Rent $2300 - $2800

Lovely home tucked away in northern Key West w/shared pool, near golf - dogs OK! Key West, Florida, Listing ID: 26103

Bring your family, friends, dog (for a small nightly fee) and golf clubs along for a stay in this lovely two-bedroom, one-and-a-half-bathroom home! A great location near the golf course, along with plenty of amenities (including a shared pool), ensure this will be a vacation to...

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  • 820
  •  2
  •  1 1/2
Monthly Rent $4000 - $6500

Oceanview home w/ shared pool & hot tub - near golf & more. Dogs OK! Key West, Florida, Listing ID: 26104

Two bedrooms, two bathrooms, dog-friendly accommodations, and a stunning ocean view make this Key West condo ideal for your next Florida getaway! Your home is right near the marina, and only a short distance from the Key West Golf Club. The Key West Tropical Forest &...

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  • 1024
  •  2
  •  2
Monthly Rent $3600 - $7000

Breezy home w/central location in Key West near shopping, dining, etc. - dogs OK Key West, Florida, Listing ID: 26106

Dive into the thick of it with this dog-friendly home in downtown Key West. One of Florida's most amazing island towns awaits, right outside your door. Your home is set right on Duval Street. You're never more than a few minutes from any shopping or dining you might need....

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  • 1577
  •  2
  •  2
Monthly Rent $4500 - $10500

Centrally located home w/ private pool 3 blocks to Duval St - dogs OK! Key West, Florida, Listing ID: 26108

Swim in the private pool, head to downtown Key West to soak up the sights, or relax in a breezy dog-friendly home - with this amazing cottage, everything is possible! Your new home away from home sits on a hill only a few blocks from the beating heart of Key West. Shopping,...

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  • 1507
  •  2
  •  2
Monthly Rent $3600 - $9500

Welcoming home w/ shared pool boasts great Old Town location - dogs welcome! Key West, Florida, Listing ID: 26114

Amenities like a shared pool, dog-friendly accommodations, and a fantastic location all make this home perfect for your next trip to the Florida Keys! Your new getaway of choice is only a block away from Duval Street, right near Key West's Old Town. Shops and restaurants are...

  • Home
  • 1275
  •  2
  •  3
Monthly Rent $4700 - $8900

Stunning home near beach and town with private hot tub and shared pool - dogs OK Key West, Florida, Listing ID: 26118

Make your next stay in the Florida Keys one to remember with this amazing home in Key West! Three bedrooms, three bathrooms, dog-friendly accommodations, and a shared pool ensure your next trip to the tropics will be one you'll always remember. Your home is only a block away...

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  • 1140
  •  3
  •  3