Key West, Florida Listings

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Monthly Rent $4800.00 - $10000.00

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 $6000.00 - $13400.00

Dog-friendly, cozy home w/ private pool & hot tub - walk to must-see attractions Key West, Florida, Listing ID: 26021

If Key West is on your travel itinerary, make this lovely dog-friendly rental for six your home away from home and spend your time lounging by your private pool and spa. Located in Historic Bahama Village, this home is one block away from the world-famous Duval Street, where...

  • Home
  • 0
  •  3
  •  2
Monthly Rent $3000.00 - $6150.00

Dog-friendly condo in prime location - walk to dining & sights, near the beach! Key West, Florida, Listing ID: 26073

Get away from it all and head to Key West for a sun-filled vacation with this two-bedroom, two-bath condo for six and enjoy easy access to restaurants, attractions, and the beach. You can also bring your beloved dog along for a small nightly fee! You'll be located on the...

  • Condo
  • 0
  •  2
  •  2
Monthly Rent $2500.00 - $7500.00

Enchanting seaside cottage w/private pool, off-street parking, & prime location Key West, Florida, Listing ID: 26080

Come explore the rich history, decadent beaches, and seaside dining spots when you book your getaway to this Key West cottage. Filled with charm for up to five guests to enjoy, this home offers off-street parking, a private pool, and a location that puts you close to all of the...

  • Home
  • 824
  •  1
  •  2
Monthly Rent $2500.00 - $6300.00

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 $2100.00 - $6500.00

Charming cottage w/a private parking spot and private hot tub Key West, Florida, Listing ID: 26087

Trade in the daily grind for sugar-sand beaches and gentle ocean breezes when you book your getaway to this lovely Key West cottage. Featuring a private parking spot and a bubbling hot tub, stress won't stand a chance. Located just a mile from Fort Zachary Taylor Historic...

  • Home
  • 750
  •  2
  •  2
Monthly Rent $2400.00 - $6300.00

Dog-friendly seaside escape with shared pool, hot tub, tennis courts, and more! Key West, Florida, Listing ID: 26088

Bring your bathing suit, camera, and up to two canine companions (for a small nightly fee) for your next trip to this Key West cottage. With room for up to four guests, private parking, and resort amenities like a shared pool, hot tub, and tennis courts, fun will always be close...

  • Condo
  • 1178
  •  2
  •  2
Monthly Rent $3700.00 - $10000.00

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 $3400.00 - $6700.00

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 $2000.00 - $3900.00

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 $3700.00 - $10300.00

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 $2200.00 - $4100.00

Gorgeous home w/ convenient location features shared pool, hot tub, & more! Key West, Florida, Listing ID: 26117

Two bedrooms, two bathrooms, and incredible beauty await you in this condo in Key West! The Florida Keys are yours to cherish, with amenities like a shared pool and an outdoor shower. Thanks to its convenient location near the airport, your new home away from home is...

  • Condo
  • 800
  •  2
  •  2
Monthly Rent $4100.00 - $7000.00

Ocean-view condo with shared pool and hot tub moments away from town and beach Key West, Florida, Listing ID: 26179

Soft sands, cool drinks, and breathtaking sunsets are at your fingertips at this beautiful Key West condo. You'll be moments from beaches, bars, and restaurants, with resort style perks like a pool and hot tub waiting back at the condo! You and your loved ones will love this...

  • Condo
  • 1658
  •  3
  •  2

Dog-friendly home with private pool and great central location! Key West, Florida, Listing ID: 26867

Ideal for families, this dog-friendly home is perfectly placed for fun in the Florida Keys. Perks like a private pool will keep you comfy between enjoying the sand, sun, and surf of the tropics! While the immediate neighborhood is low-key, this home is still close enough to...

  • Home
  • 915
  •  2
  •  1

Gorgeous modern home with private pool near beach, fishing and more Key West, Florida, Listing ID: 26868

Get ready to see a whole new side of the sunshine state from the comfort of this home in Key West. You'll enjoy perks like a private pool, as well as a great location just a few blocks from the beach! Nestled on the eastern edge of Key West, this home is a short walk from the...

  • Home
  • 1581
  •  2
  •  2
Monthly Rent $3300.00 - $5000.00

Beautiful dog-friendly townhome in central location w/ shared pool Key West, Florida, Listing ID: 26869

Enjoy the unbeatable location of this two-bedroom, dog-friendly Key West townhouse. This home features four covered balconies, including one that overlooks the community pool and central courtyard. Ceiling fans and central A/C keep the Florida heat at bay, while the private...

  • Condo
  • 1120
  •  2
  •  2 1/2

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Monthly Rent $2500.00

6 MONTH SEASONAL RENTAL POMPANO BEACH CONDO - FANTASTIC VIEWS Pompano Beach, Florida, Listing ID: 24578

4-6 MONTH MINIMUM SEASONAL RENTAL Spacious open floor plan, 2BR/2BA top floor unit. Private balcony with fabulous views of the waterway, pool and hot tub. Assigned parking with plenty of guest parking. Near casino and racetrack.

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Details No Image Available

$Multi-Month Discount!

Monthly Rent $4500.00

Ground floor 3 bedroom condo,situated near Barefoot beaches,gated community. Naples, Florida, Listing ID: 25318

Our property overlooks a lake, fountain and small waterfall. It is situated in lush grounds well tendered gardens. It is very peaceful even in high season. The property it self is furnished and well maintained to a very high standard. There are 9 local beaches the nearest...

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Monthly Rent $1700.00 - $2800.00

Bayfront home with shared pool, tennis on-site, shared boat ramp! Key Largo, Florida, Listing ID: 26000

Kick off your shoes and leave your worries behind when you book your next seaside getaway to this bayfront Key Largo home. Boasting shared amenities like a pool, tennis courts, and a community boat ramp, your stay promises to be stress-free. Set on the north shore of Key...

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  • 778
  •  2
  •  2
Monthly Rent $2900.00 - $3500.00

Waterfront getaway with private dock - great for fishermen and boaters! Key Largo, Florida, Listing ID: 26001

Surround yourself with water views and canal-front convenience when you book your next stress-free getaway to this Key Largo retreat. Boasting views from nearly every window and private dock slipping into vacation mode will be a breeze. Set near the calm waters of Florida's...

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  • 1800
  •  3
  •  2 1/2
Monthly Rent $2000.00 - $3500.00

Classic lakefront condo w/shared pool, sauna - lots of amenities, including golf Naples, Florida, Listing ID: 26115

Head to Naples for your next Florida getaway and revel in high-end amenities, including a shared resort-style pool and sauna, clay tennis courts, golf, and much more. Perfect for a small family or group of friends wanting to escape the din of life's hustle and bustle, this...

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  • 1107
  •  2
  •  2
Monthly Rent $3000.00 - $3200.00

Classy condo w/ shared pool & hot tub, panoramic ocean views from private lanai! Marco Island, Florida, Listing ID: 26122

When you want to vacation in style in a beautiful tropical setting, escape to this pleasant Marco Island condo. You and your guests will enjoy amenities like a shared pool and hot tub, as well as gorgeous panoramic views from your private lanai and walking distance to the...

  • Condo
  • 1296
  •  2
  •  2
Monthly Rent $2800.00 - $4800.00

Waterfront, golf community home w/ private heated pool, overlooking a lake Naples, Florida, Listing ID: 26123

Treat yourself to a stress-free, fun-filled getaway when you book your next vacation to this Naples home. Whether you're driving down the lush fairways, floating in your private pool, or basking in your lake views, this home ensures that you'll be able to unwind in style....

  • Home
  • 1691
  •  3
  •  2
Monthly Rent $2000.00 - $6800.00

Pristine condo w/ shared pool, hot tub & sauna - ocean views, walk to beach! Marco Island, Florida, Listing ID: 26124

Escape to Marco Island for your next sun-filled getaway and stay in this pristine two-bedroom condo with a shared pool, hot tub, sauna, and tennis. You'll also enjoy lovely ocean views from the balcony and easy beach access! This rental is located on the south end of the...

  • Condo
  • 1457
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3500.00 - $3700.00

Beautiful two bedroom condominium with a picturesque view overlooking a lake and the 8th tee box on the golf course. Naples, Florida, Listing ID: 26189

Seasonal Rental - Naples Heritage Golf and Country Club - Rate negotiable if rented for more than 3 months or May-December. Currently available May 2020 to December 2020. Leased from January 1, 2020 to April, 2020. Beautiful 2-bedroom 2-bath condo located on the 2nd...

  • Condo
  • 1194
  •  2
  •  2
Monthly Rent $4200.00 - $4700.00

Centrally-located condo near shopping, dining, features shared pool and tennis Marco Island, Florida, Listing ID: 26203

Perfect for small families, this condo comes with everything you need for an exciting South Florida getaway, complete with a shared pool, tennis courts, and easy access to shops and restaurants. You and your loved ones will be on northern Marco Island, just a short walk away...

  • Condo
  • 804
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $1750.00

Secret little gem in Dania Beach Fl. Newly renovated 1/1 unit available for Snow Birds looking for a 4-6 month rental. Dania Beach, Florida, Listing ID: 26487

The Sunshine Villas are a private community of Canadian and American Snow Birds located in the heart of Dania Beach. This secret little gem offers amazing proximity to the Cities, Airports, Beaches, Casinos, shopping and even the Everglades and beautiful Florida Keys and Key...

  • Condo
  • 620
  •  1
  •  1
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2600.00 - $4900.00

+++ 2-BED 2-BATH LUXURY CONDO IN NAPLES, FLORIDA ++ LAKE VIEW ++ VERY PRESTIGIOUS AREA ++ NEAR DOWNTOWN AND BEACHES! +++ Naples, Florida, Listing ID: 26574

DESCRIPTION: Bright corner unit. Fully furnished. 2 bedroom, 2 full bathrooms. Heated pool. Tennis courts. Close to beaches, restaurants, shopping, golf, tennis and attractions. Incredible lake view from everywhere in your living area. Large private screened lanai...

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  • 1500
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2500.00

Cypress Bend condo, 5 miles from beach! Lakeview, 2nd floor, corner unit Clean Pompano Beach, Florida, Listing ID: 26745

Plenty of parking, master parking space right in front of unit, stairs or elevator access, 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...

  • Condo
  • 1000
  •  2
  •  2

Dog friendly home on wide canal with amazing water views! Tavernier, Florida, Listing ID: 26862

This home is perfect for anyone coming to the Keys to spend time on the water. The two-story home sits on the widest canal in Hammer Point that leads to Florida Bay and has its own private dock capable of anchoring a boat up to 40 feet. Back on land, you and your party have a...

  • Home
  • 1248
  •  2
  •  2
Monthly Rent $5000.00 - $5400.00

Charming waterside getaway w/private pool-close to golf & beach Naples, Florida, Listing ID: 26865

Luxury and relaxation are waiting for you at this family-friendly Naples home. Boasting a private pool, jacuzzi hot tub, and covered lanai, this home surrounds you with a peaceful ambience and opportunities for fun! Set in the quiet Fiddlers Creek neighborhood, about 13 miles...

  • Home
  • 2583
  •  3
  •  3
Monthly Rent $4300.00
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2250.00

HALLANDALE BEACH FRONT BEAUTIFUL APARTMENT FOR SEASONAL RENTAL NEAR GREAT RESTAURANTS, SHOPS AND CASINO Hallandale Beach, Florida, Listing ID: 27128

Awesome beachfront apartment in Parker Tower for seasonal rental in beautiful Hallandale Beach. It's a 900 square feet, 1 bedroom (w/ walk-in closet), 1-1/2 bathrooms, fully furnished (cable TV, Wi-Fi, electric and water utilities included) with all kitchen appliances. The...

  • Apartment
  • 900
  •  1
  •  1 1/2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $4000.00 - $4500.00

AMAZING WATER AND SUNSET VIEW KEY LARGO TOWN-HOME 3BR/2BATH Leave the stress! Key Largo, Florida, Listing ID: 27176

Gorgeous luxury Town-home located in the private community of Marina del Rey. Spacious 3 bedrooms and 2 bathrooms. Come and relax or invite the family and get together for a family vacation. Located very close to many convenient stores, restaurants, and attractions. To name a...

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BEAUTIFUL WATER FRONT HOME W/ PRIVATE BEACH, JACUZZI, DOCK, RAMP, LIFT, KAYAKS, ETC. Key Largo, Florida, Listing ID: 27311

Beautiful home directly on the water, being able to watch stunning sunsets all year around! 180 degrees of open water views. Imagine yourself being able to enjoy your glass of wine every afternoon watching the sunset. Tranquil waterway perfect for swimming, paddle-boarding,...

  • Beach Home
  • 1,750
  •  2
  •  2

beautiful beach front property,steps to the water Key Largo, Florida, Listing ID: 27322

  • Home
  • 1,750.00
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $4200.00 - $5000.00

Stunning modern 1 bedroom condo equipped with all amenities. Beautifully furnished,excellent location with ocean views. Hollywood, Florida, Listing ID: 27329

Rent Nightly or monthly. Beautifuly furnished unit with modern decorating. This place is on a top floor and has spectacular views of both the bayside, city and ocean views. It is equipped with everything you need. all you have to do is bring a packed bag. It is located in a...

  • Condo
  • 1000
  •  1
  •  1 1/2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3500.00

Very beautiful large spacious furnished 2 bedroom/2 bath condo intercoastal to beach Sunny Isles Beach, Florida, Listing ID: 27330

This is a very large beautifully furnished unit.This unit has been completely renovated with new floors,cabintry, appliances,furniture. Unit faces northeast so there is lots of bright light shining in throughout the day. It has floor to ceiling sliding glass doors, kitchen has...

  • Condo
  • 1400 sq ft
  •  2
  •  2