
Pet-friendly vacation rentals in Summerland Key
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Summerland Key
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Cottage 30 min from Key West, free parking, pool
Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

Family House, 2 K BR's, Private Spa/Deck, 2 pools.
The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 56” Smart TV. Bring your Netflix, Amazon or other UN and PW for your favorite programming. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

Tropical Paradise
Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.

Ocean~View w/ Dock, Pool, Kayaks, King Bed
Experience waterfront luxury in Venture Out on peaceful Cudjoe Key! Enjoy stunning Atlantic Ocean views, amazing sunsets, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Keep your boat at the house and reach the Atlantic or Gulf in minutes. Near Key West, this updated Keys getaway includes resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, especially lobster season in August, so book now!

Flakey's
Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!
Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Waterfront Anchor House with Boat Basin & Ramp!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Waterfront Cozy Modern Retreat w/Deep Canal
Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

Cottage
Experience island living at Sugarloaf RV Resort's NEW Cottages in the Lower Keys, just 25 minutes from Key West. These Two-Bedroom Cottages sleep up to 4 guests with 2 Queen beds. Features include a kitchenette with double burner stovetop, dorm fridge, microwave, single serve coffee maker, toaster, plus outdoor seating. Coastal charm with keys-style design and a private patio perfect for morning coffee or sunset relaxation.
Popular amenities for Summerland Key pet-friendly home rentals
Pet-friendly house rentals

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

Duval Vibes • Pool • 10 Guests

Oceanfront mermaid house pool and dock

Waterfront Private Home w/Pool-Family&Pet Friendly

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

Oceanview Marathon - Screened Porch, Theater & Bar

Golf Coast Oasis near Sombrero Beach
Pet-friendly home rentals with a pool

Castaway Cove: Pet-friendly 2/2 condo near beach!

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Waterfront Condo Dock Pool Near Duval St

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

Luxurious 40' Sailing Yacht!

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

Oceanview condo w/pool, jacuzzi
Private, pet-friendly home rentals

Powell Family Resort

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Starlight Serenity - Hideaway with Stunning Views

Key West Luxury Houseboat at Yacht Club Resort

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

Easy Ocean Access 30' Dock House Pool Cabana Club

Water, Water Everywhere! "The Wheel House"

New Waterfront 2/1 Cabin With Loft at Bonefish Bay
When is the best time to visit Summerland Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $424 CAD | $392 CAD | $436 CAD | $328 CAD | $320 CAD | $320 CAD | $324 CAD | $323 CAD | $299 CAD | $310 CAD | $327 CAD | $382 CAD |
| Avg. temp | 21 °C | 22 °C | 24 °C | 25 °C | 27 °C | 29 °C | 30 °C | 30 °C | 29 °C | 27 °C | 25 °C | 23 °C |
Quick stats about vacation rentals that are pet-friendly in Summerland Key

Total vacation rentals
Explore 150 vacation rentals in Summerland Key

Nightly prices starting at
Summerland Key vacation rentals start at $111 CAD per night before taxes and fees

Verified guest reviews
Over 1,670 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space and kid-friendly amenities

Vacation rentals with a pool
110 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
120 of Summerland Key vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Summerland Key rentals

4.8 Average rating
Summerland Key stays are highly rated by guests—averaging 4.8 out of 5!
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- Sombrero Beach
- Smathers Beach
- Ernest Hemingway Home & Museum
- Bahia Honda State Park
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Key West Butterfly & Nature Conservatory
- Fort Zachary Taylor Historic State Park
- Dolphin Research Center
- Southernmost Point
- Key West Lighthouse Museum
- Boca Grande Key
- Conch Key
- Mel Fisher Maritime Museum
- Curry Hammock State Park
- Key West Aquarium
- Truman Little White House





