Key West, Florida Listings

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Welcoming home w/ private pool & covered porch - walk to dining & attractions Key West, Florida, Listing ID: 26008

Head to the Keys for your next Florida getaway and set yourself up for comfort and convenience when you stay at this welcoming, well-equipped home with a private pool and charming covered porch. You'll be situated only a mile from South Beach, so the sand and water are...

  • Home
  • 1440
  •  3
  •  3

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

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

Dog-friendly home w/ private pool - walk to parks, shopping, & the beach! Key West, Florida, Listing ID: 26017

This Key West home is waiting for you and your group of up to six to come make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach of the beach, parks, and all the necessities. Walk to Higgs Beach and the pier, Indigenous Park, and dinner...

  • Home
  • 1672
  •  3
  •  3

Dog-friendly, comfortable home w/ shared pool - close to beaches & attractions Key West, Florida, Listing ID: 26019

Head to Key West and revel in access to a shared pool, dog-friendly accommodations, and close proximity to beautiful beaches and major attractions when you stay at this three-bedroom, three-bath home for six. This rental is located in the heart of Old Town, putting you one...

  • Home
  • 1455
  •  3
  •  3

Stylish, inviting home w/private pool in heart of downtown - walk to everything! Key West, Florida, Listing ID: 26043

Make this stylish, three-bedroom, two-and-a-half bath home for six yours when you come to Key West, and revel in amenities like a private heated pool and an ideal location. Located in downtown Key West, this home is a mere one block from Duval Street. Southernmost Point and...

  • Home
  • 1178
  •  3
  •  2 1/2

New home w/ private pool & rooftop patio - ideal location & steps from beach! Key West, Florida, Listing ID: 26058

This four-bedroom, three-and-a-half bath Key West home has just what you and your group of up to eight need for an awe-inspiring Florida beach getaway, including a private heated pool, rooftop patio, and easy access to the beach and major attractions. You'll be a few steps...

  • Home
  • 1912
  •  4
  •  3 1/2

Home w/private pool & hot tub - walk to everything Key West, Florida, Listing ID: 26060

Sink into the comfort of this lovely Key West home for 10, and enjoy a luxurious Florida getaway, complete with private pool and hot tub and excellent location, allowing you to walk to dining and all the sights. This home is located on a quiet street in Old Town Key West, a...

  • Home
  • 2352
  •  4
  •  3 1/2

Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks Key West, Florida, Listing ID: 26063

Bring your large group of up to 18 to Key West and stay in this spectacular five-bedroom, three-bath oceanfront home for an unforgettable Florida vacation. Amenities include a private pool, massive deck with seating, lush surrounding gardens, and two private docks, as well as...

  • Home
  • 3332
  •  0
  •  

Cozy, dog-friendly home w/ patio & private pool - walk to dining & shopping! Key West, Florida, Listing ID: 26071

Head to Key West for a rejuvenating reprieve and enjoy the patio and private pool at this cozy, two-bedroom home conveniently situated near dining, shopping, and all the must-see sights. Your beloved family dog is also welcome for a small nightly fee. You'll be about two...

  • Home
  • 792
  •  2
  •  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

Welcoming, conveniently-located, dog-friendly home - walk to everything! Key West, Florida, Listing ID: 26074

If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island. You'll be in the center of Key West within walking distance to restaurants, bars, and shops, as well...

  • Home
  • 705
  •  1
  •  1

Fully-renovated home w/ yard, porch, shared pool - one block from Duval Street Key West, Florida, Listing ID: 26075

Originally built in 1933, this fully renovated, three-bedroom home has a yard, a cozy front porch where you can sit back and watch the day go by, and room for up to eight guests (six comfortably). Stroll to shopping, entertainment, and beaches, all within a few blocks of this...

  • Home
  • 1051
  •  3
  •  2

Dog-friendly home w/ private pool offers fantastic location in central Key West Key West, Florida, Listing ID: 26077

Leave your worries behind with a relaxing trip to the Florida Keys courtesy of this lovely vacation home! This traditional home in Key West features modern amenities and a location perfect for sightseeing. Nestled in Key West's old town, this home for four puts you only a few...

  • Home
  • 1062
  •  2
  •  1
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

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 $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 $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

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
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

Sprawling condo w/ ocean views, dock, & shared pool - dog-friendly! Key West, Florida, Listing ID: 26557

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
  • 1300
  •  2
  •  2 1/2

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

Similar Properties


Monthly Rent $800.00 - $1400.00

Ground Floor 1 BR, 1.5BA West of Ft. Lauderdale near golf, Sawgrass Mall Tamarac, Florida, Listing ID: 24275

Nice ground floor unit with updated kitchen, all new IKEA furniture. 1 large bedroom with Queen bed & full bath, one half bath in hallway. Couch in living room is a sleeper and porch is enclosed with a couch bed. Ceiling fans in living room & porch. For 2 persons, but can easily...

  • Condo
  • 600-800
  •  1
  •  1 1/2

Bright and cheery family-friendly home w/soaking tub, dock access, & ocean views Key Largo, Florida, Listing ID: 26003

Get the whole group together for a sun-soaked getaway they'll never forget when you book a trip to this waterfront Key Largo home. Boasting ocean views, easy beach access, and room for up to nine guests, this family-friendly gem will make sure that you enjoy your well-deserved...

  • Home
  • 5912434
  •  4
  •  2 1/2
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 $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...

  • Condo
  • 1500
  •  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
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...

  • Beach Home
  • 1,200
  •  3
  •  2

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
  • 2000
  •  5
  •  3
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
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3000.00 - $6000.00

Luxury Fiddler's Creek 3Br condo in gated golf resort community with tennis and multiple pools, paths, spa, fitness Naples, Florida, Listing ID: 27548

This luxury resort offers security at gate. The community is over 54,000 acres with walking paths, nature areas, water features, and gorgeous landscaping. Golf course on site. Tennis and pickleball. Each small community has a private pool and the clubhouse has a large waterfall...

  • Condo
  • 2100
  •  3
  •  2
Monthly Rent $5500.00

Ocean breezes and spectacular sunrises every morning from the Pier and the Marina. Great way for a gateway. 3 Floors. Key Largo, Florida, Listing ID: 28211

4 bedroom and 3.5 baths (Sleeps up to 10 People) 2 balconies, 3 floors, 1st floor storage & carport area. Neighborhood Feature: Clubhouse, Community Pool, Community Boat Ramp, Other Area Features, Community Dockage, Fire Hydrant, Manager on Premises, Security: Manned...

  • Home
  • 2665
  •  4
  •  3 1/2
Monthly Rent $5500.00

Walking distance from the ocean! KEY LARGO, Florida, Listing ID: 28212

Ocean breezes and spectacular sunrises every morning from the Pier and the Marina. ClubHouse and steps from the ocean.

  • Home
  • 2665
  •  4
  •  3 1/2