$12,500 per month
- 4 Beds
- 4 Baths
- 2,952 Sq Ft
- Property for Rent
21640 Overseas Hwy, Summerland Key, FL 33042
21640 Overseas Hwy, Summerland Key, FL 33042$12,500 per month
21640 Overseas Hwy, Summerland Key, FL 33042
21640 Overseas Hwy, Summerland Key, FL 33042$6,500 per month
18 W Circle Dr, Key West, FL 33040
18 W Circle Dr, Key West, FL 33040$5,500 per month
59 Palm Dr, Key West, FL 33040
59 Palm Dr, Key West, FL 33040$2,700 - $3,000 per month
Coco Palms
2 Beds
21585 Overseas Hwy, Cudjoe Key, FL 33042
$5,490 per month
31547 Avenue D, Big Pine Key, FL 33043
Come see this immaculate 2 Bedroom 2 Bath Big Pine Key Waterfront home with its Wonderful Water Views! It is available for a seasonal rental, so come on down and enjoy the Florida winter weather! It has a well equipped kitchen for your convenience and is only 5 years old. Please see the attached photos. You'll be glad you did! Only 30 miles to Key West and all of the other Points of Interest in
Philip Vias LoKation
$3,900 - $5,500 per month
Little Torch Cottages
2 Beds
28501 Channel View Dr, Little Torch Key, FL 33042
$4,800 per month
29283 Coconut Palm Dr, Big Pine Key, FL 33043
Welcome to Coconut Palm Drive--a hidden gem in one of Big Pine Key's peaceful residential neighborhoods. This 3 bedroom, 1.5 bath island home offers vaulted ceilings, crown molding, and an open-concept layout that brings in natural light and a spacious feel. The tropical backyard is fully fenced for privacy and features mature banana trees. A generous downstairs storage area offers endless
Lisa Cattran Engel & Volkers Marathon
$3,525 per month
29822 Frostproof Rd, Big Pine Key, FL 33043
Property Id: 2218567Enjoy comfort and privacy in this elevated 2-bedroom, 2-bath home featuring an extra bedroom, open floor plan and vaulted ceilings for a bright, airy feel. The living room and master bedroom each open through French doors onto a balcony, while the bonus bedroom offers its own private sliding door access. Central A/C and heat keep the home comfortable year-round. Relax
$3,600 per month
30964 Nathalie Rd, Big Pine Key, FL 33043
Unfurnished long term rental. Nicely upgraded and available for occupancy now.
Roberta Mira Sunshine State Realty Services
$6,592 per month
886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042
Loggerhead Lagoon is a stunning, tropically themed 3-bedroom 2-bathroom home located on a large private lot that offers covered parking, a boat dock, and direct access to the Gulf of Mexico. This rare find boasts a lush outdoor area full of beautiful palms, sun loungers, and tons of Florida sunshine. Located in Sugarloaf Key, just 19 miles from Key West and the world-famous Duval Street, this
$5,000 per month
Unlisted Address
3 bedroom/3 bathroom 1500 sqft canal front home. This property includes 45' of dockage in addition to a 15,000 pound boat lift. Inside you will find two en suite bedrooms & baths, and an open living and kitchen. There is also a large sized screened in covered porch overlooking the yard and canal. Pets are allowed with an additional one time pet fee of $250. Utilities paid by tenant (water and
Nick Boumerhi Meyer and Boumerhi Realty LLC
$3,500 per month
30612 23rd Ln, Big Pine Key, FL 33043
Property Id: 2240886Discover the beauty of Big Pine Key from this delightful 2-bedroom house. With a king bed and a queen bed, guests can relax in comfort. Enjoy the convenience of WiFi, AC, and a washing machine during your stay. The 2 bathrooms are equipped with all of the conveniences of home. Located between the Back Bay and the Ocean. Property sits on an acre lot, enjoy the breezy,
$5,000 per month
24840 Park Dr, Summerland Key, FL 33042
{ WOW } Try and find a rental in the Lower Florida Keys! Then, yet again, one with 3 bedrooms, 2 Full baths and spacious Kitchen, Livingroom, Dinning open concept layout. Welcome to living in Summerland Key Cove.Live where others vacation -- in Summerland Key Cove, just 25 miles from Key West. Whether you're a boater, pilot, fisherman, or someone who simply enjoys walking their dog by the water,
Thomas Murphy LAER Realty
$4,950 per month
486 Airport Dr S, Summerland Key, FL 33042
Property Id: 2182502Enjoy Florida Keys living on a wide, flow-through boating canal with a concrete seawall and davits — perfect for your boat or water toys. relax on the 400 sq. ft. screened porch, or take advantage of the massive 1,300 sqft garage/airport hangar downstairs — plenty of room to park all your toys and gear. Upstairs offers 3 bedrooms, 2 baths, and 1,300 sq. ft. of bright,
$6,000 per month
21660 Overseas Hwy, Summerland Key, FL 33042
Private Oceanfront Beach House - Annual Rental Available.Your private slice of the Florida Keys, just 20 minutes from Key West. This direct oceanfront home offers sweeping Atlantic views and the ultimate coastal escape.Inside, you'll find an airy layout with plenty of natural light, stainless steel appliances, French doors, impact-rated sliders, doors, and windows, plus updated AC units for
Kelly Gardner Bluescape Real Estate
$7,500 per month
18954 Acosta Rd Unit ID1297838P, Summerland Key, FL 33042
Escape to paradise and feel at home in this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key, accommodating up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails.This charming home features a spacious open-concept floor plan designed for relaxation and connection. Natural light pours into the airy interior,
$4,800 per month
27316 Cayman Ln Unit 1,2, Summerland Key, FL 33042
House in the Lower Keys Seasonal Rental. Available Sept 15, 2025 – Villa Marquesa, Lower Keys waterfront retreat! Spacious furnished home ideal for families, multi-gen living, or work-from-paradise. Corner lot on 2 wide canals with deep water access & 2 private docks (45’ & 15’). Upstairs: 3BR/1BA, 1,200 SQF, open kitchen, dining, living & TV rooms, water views. You can also rent downstairs unit,
Hamlet Garcia Proxy Realty Group LLC
$5,500 per month
28515 Channel View Dr, Little Torch Key, FL 33042
Current resident moving out on 10/31/25.This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished townhome for rent on a year lease. It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated
Joseph Danieli AKT Realty LLC
$6,995 per month
30825 Ortega Ln, Big Pine Key, FL 33043
Welcome to your slice of paradise in Big Pine Key! This stunning property offers peace and privacy on a quiet street,just minutes from world class fishing, boating, and the natural beauty of Bahia Honda State Park. This charminghome comes fully furnished and features an open-concept layout, modern updates, and coastal finishes throughout. relax on the coveredporch, entertain on the
Walter Vargas Cervera Real Estate Inc.
$8,500 per month
1540 Lantana Ln, Big Pine Key, FL 33043
FISHERMANS DREAM HOUSE! BRING YOUR BOATS TO THIS AMAZING 3/2 HOUSE SECLUDED ON A CORNER LOT WITH 190FT OF SEAWALL. BOAT RAMP MINUTES AWAY. ICE MAKER AT THE OUTSIDE BAR.ENJOY THE POOL, OPEN DECKS, COCKTAILS AT THE OUTSIDE BAR, AND THE ADORABLE KEY DEER ROAMING THE NEIGHBORHOOD. SLEEPS 8. AVAILABLE FOR MONTHLY RENTALS TOO. DISCOUNTED PRICES FOR MULTIPLE MONTH RENTALS AND OFF SEASON.
Andrea Lennon Vylla Home
$5,800 per month
3770 Park Ave, Big Pine Key, FL 33043
Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for
Mary Jo Selden DomainRealty.com LLC
$5,800 per month
3770 Park Ave, Big Pine Key, FL 33043
Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for
Mary Jo Selden DomainRealty.com LLC
$4,900 per month
74 Pelican Ln Unit 1, Big Pine Key, FL 33043
Completely remodeled property, 2024 roof, new floors, termite treatment done 2025, fully furnished, with an excellent location 30 minutes from Key West, restaurants, schools, beaches, recreational centers and everything you need for a quiet and pleasant life, all nearby
Yunior Molina My Realty Group, LLC.
$3,950 per month
28511 Channel View Dr, Little Torch Key, FL 33042
Current resident moving out on 12/31/25.This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent on a year lease.It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, stackable washer and dryer, hurricane windows and doors, two balconies, 2 heated and chilled community pools, gym, sauna, marina
Joseph Danieli AKT Realty LLC
$13,500 per month
28502 Channel View Dr, Little Torch Key, FL 33042
This is a 3 story furnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.
Joseph Danieli AKT Realty LLC
$12,000 per month
441 La Fitte Rd, Summerland Key, FL 33042
** SHORT-TERM RENTAL ** Stunning open water house with high ceilings, open floor plan, covered screen porch, and open deck for the sun lovers! New deck with a heavy-duty boat lift in place (15,000 pounds) in one of the cleanest waters in the FL Keys! Metal roof, New A/C, Water Heater, and a Front aluminum fence with beautiful landscaping This home is located in one of the best neighborhoods in
Carolina Gil Caralex Intl Realty Group Corp
$1,450 per month
29859 Overseas Hwy Unit A14, Big Pine Key, FL 33043
🌴 Big Pine Key Lot for Rent - RV or Tiny Home Ready! 🌴Enjoy the Florida Keys lifestyle in this beautiful lot located in a desirable condominium community in Big Pine Key, just off U.S. 1 and close to everything!🏝️ Community Features:Heated pool for year-round enjoymentWasher/dryer available for tenantsSafe, friendly neighborhoodSteps from the bus stop, shops,
Graciela Lozano KeysLifestyle Real Estate (KW)