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

Similar Properties


Monthly Rent $1300 - $2200

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

NOW ACCEPTING RESERVATIONS FOR FALL AND WINTER 2018-2019 Unique one bedroom one bath canal front home. Stilt home with living area on second floor. Four hundred square foot Florida room with view down canal with quick access to San Carlos Bay and Long Cut. Covered boat slip...

  • Home
  • 1000-1200
  •  1
  •  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...

  • Home
  • 1000-1200
  •  2
  •  2 1/2
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;...

  • Condo
  • 2261
  •  3
  •  2
Monthly Rent $9500 - $11000

Magnificent Home mouth of a wide canal in Tavernier Phenomenal Open Water View Plantation Key, Florida, Listing ID: 24309

***FALL SPECIAL*** RECEIVE 20% OFF RENT FOR ALL BOOKINGS IN NOVEMBER AND DECEMBER. MINIMUM STAY: 29 DAYS This magnificent home is located at the mouth of a wide canal in Tavernier and offers phenomenal open water views. The furnishings are new and provide a comfortable...

  • Home
  • 2500-3000
  •  4
  •  3
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...

  • Home
  • 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 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best.  Conveniently located on a deep and wide canal with easy access to...

  • Home
  • 2000-2500
  •  3
  •  2 1/2
Monthly Rent $9975

!Tropical Retreat Wonderful Home Billiard/Game Room Pool Boat Dock A True Gem!!! Plantation Key, Florida, Listing ID: 24314

*****SUMMER SPECIAL ***** RECEIVE A $100 VISA GIFT CARD FOR ALL BOOKINGS BETWEEN JUNE 1, 2018 AND AUGUST 31, 2018. RESERVATION MUST BE MADE BY MAY 31, 2018. Minimum Rental: 1 Month Spacious elegant home with pool and dock. Gently swaying palm trees greet you at the...

  • Home
  • 2500-3000
  •  4
  •  3
Monthly Rent $3950

"Sunshine Place" Perfect for one or two people who treasure the tropical Live!!! Islamorada, Florida, Listing ID: 25398

"Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who...

  • Home
  • 800-1000
  •  1
  •  1
Monthly Rent $5200

harming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! Islamorada, Florida, Listing ID: 25667

MINIMUM RENTAL 1 MONTH Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom ...

  • Home
  • 1494
  •  3
  •  2
Monthly Rent $1200 - $2900

Coach Homes of Berkshire Lakes Naples Florida, Pet Friendly, Friendly Community, Close to 5th Avenue Downtown Naples Naples, Florida, Listing ID: 25711

This tastefully decorated condo unit is located on the ground floor of a 2 story condo complex and comes with attached garage that allows direct access to the unit. It is a 10 minute drive to the famous 5th Avenue shopping, dining and entertainment district of Olde Naples as...

  • Condo
  • 1200
  •  2
  •  2
Monthly Rent $4800 - $10600

Cozy, chic cottage w/ private pool - close to beach and dog friendly, too! Key West, Florida, Listing ID: 26007

Make this cozy and chic Key West cottage your home away from home for your next Florida vacation, and revel in a private pool, deck, and covered back porch, as well as close proximity to the beach. And the real bonus: you can bring your favorite canine friend along,...

  • Home
  • 1400
  •  3
  •  2
Monthly Rent $6150 - $16350

Historic home in Old Town w/ private pool & detached cottage - dogs OK Key West, Florida, Listing ID: 26011

Come experience Key West in all its glory when you stay in this dog-friendly historic home featuring a private pool and lush tropical gardens. Your group of up to six will be set for a comfortable and convenient stay, and the detached cottage is the perfect spot for the teenager...

  • Home
  • 1599
  •  3
  •  3
Monthly Rent $5000 - $13000

Dog-friendly home w/ private pool & space to lounge - walk to everything! Key West, Florida, Listing ID: 26013

Come to Key West and ensure your Floridian getaway is the best it can be when you make this desirable rental your home away from home. Your group of up to eight will experience tranquil comfort and tasteful style in this dog-friendly home with a private pool, luxurious patio...

  • Home
  • 1596
  •  3
  •  3 1/2
Monthly Rent $4600 - $12100

Dog-friendly home w/ private pool, jetted tub, & gardens - relax on a hammock! Key West, Florida, Listing ID: 26015

If you're headed to Key West, make the most of your vacation and stay in this comfortable dog-friendly home with a private pool, a jetted tub, and gardens for an unforgettable Florida experience. You'll be located in a quiet neighborhood in New Town and only a bike ride or...

  • Home
  • 1646
  •  3
  •  2
Monthly Rent $5400 - $11800

Spacious, canal front villa w/ private pool and hot tub - 3 dogs are welcome! Summerland Key, Florida, Listing ID: 26068

Stay in this three-bedroom, two-bath canal front villa for six when you come to Summerland Key and revel in rest and relaxation with your very own private pool and hot tub. And to make your vacation complete, you can bring three dogs along for a small nightly fee! This...

  • Villa
  • 1650
  •  3
  •  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...

  • Condo
  • 731
  •  1
  •  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...

  • Home
  • 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...

  • Home
  • 2328
  •  2
  •  2 1/2
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...

  • Condo
  • 1237
  •  2
  •  2 1/2
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...

  • Home
  • 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 &...

  • Home
  • 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....

  • Home
  • 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,...

  • Home
  • 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 $4000 - $8500

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...

  • Home
  • 1140
  •  3
  •  3
Monthly Rent $2900 - $3500

Pet Friendly! Luxurious Fully Furnished 3BR 2BA with Water View,Office, EIK, LR and All Amenities! Fort Myers, Florida, Listing ID: 26125

3 bedrrom, office space, private parking in door and out door, 20 minutes to beach, 10 minutes from major shopping mall, 20 minutes to waterparks, washer and dryer, eat in kitchen, fitness center, lake view.

  • Condo
  • 1700
  •  3
  •  2

Breezy Keys House on wide canal with immediate access to Gulf and Ocean. Great Fishing and Restaurants nearby. Islamorada, Florida, Listing ID: 26134

Updated two story Keys House on a wide canal in the Venetian Shores neighborhood of Islamorada. Heated pool, Tiki Hut and Boat Lift handling boats up to 12,500 lbs. Close to all the best restaurants in Islamorada and new Publix Supermarket. Three bedrooms and three bathrooms...

  • Home
  • 2000
  •  3
  •  3
Monthly Rent $3000 - $5300

Dog-friendly getaway w/ furnished patio & shared pool - blocks from the beach Key West, Florida, Listing ID: 26177

Enjoy this classic Key West cottage featuring a shared pool and a furnished patio, located within blocks of beaches, shops, restaurants, and museums! You can even bring the family dog for a small nightly fee. If you're here for the sand and sun, several local beaches are...

  • Home
  • 540
  •  1
  •  1

Beautiful 2 level Condo minutes from beach and downtown Palm Beach . West Palm Beach, Florida, Listing ID: 26473

Completely furnished 2 level, 2 bed, 2.5 bath condo with two assigned parking spaces directly in front as well as plenty of guest parking. Nice private patio with patio set, grill and additional chairs. Beach supplies also provided including umbrella, chairs and towels. pool,...

  • Condo
  • 1246
  •  2
  •  2 1/2
Monthly Rent $1800 - $3300

Chill in the Florida Keys Key largo, Florida, Listing ID: 26642

3 Story Town house

  • Home
  • 1500
  •  3
  •  3
Monthly Rent $2700 - $3150

Beautiful completely updated 2/2 House in Tamarac with community pool Tamarac, Florida, Listing ID: 26663

In a quiet neighborhood .This house has everything you need to make you feel at home, secure and relaxed. Also included, is basic cable TV, internet, central A/C and much more. This beautiful spacious, self-contained fully equipped house has everything you need to make you feel...

  • Home
  • 1,275 sq. ft.
  •  2
  •  2
Monthly Rent $2500

Cypress Bend condo, 6 miles from beach! Lakeview, 2nd floor, corner unit, small pet OK ! Pompano Beach, Florida, Listing ID: 26745

Plenty of parking, access to 1 Olympic size pool. And 2 other pools, 2 hot tubs, 1.5 mile walking path, on lake, short drive to beach, restaurants, groceries. 1 small pet allowed. 2 Gyms. 1 clubhouse, 1 billiard room, 3 outdoor BBQ areas. Smoking OK on screened in patio...

  • Condo
  • 1000
  •  2
  •  2