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Vacation rentals in Lakeland-Winter Haven Metropolitan Area

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Top-rated vacation rentals in Lakeland-Winter Haven Metropolitan Area

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Guesthouse in Lakeland

4.88 out of 5 average rating, 140 reviews

Cozy studio In Historic Lake Morton district

This cozy, Ground level studio is on our homes property, it has a KITCHENETTE, WITH LIMITED COOKING. It is nestled in the Historic District of Lakeland and mere steps from Florida Southern a Frank Lloyd Wright designed campus, a tour is recommended! Our cobblestone streets take you to unique neighborhood restaurants. We are walking distance of beautiful downtown Lakeland. We are between two lakes- Lake Hollingsworth, a great 3+ mile walking/running path and Lake Morton which is a bird paradise.

May 26 – Jun 2

R838 ZAR per night

Townhouse in Lakeland

4.97 out of 5 average rating, 179 reviews

Glam Townhouse in Downtown Lakeland - 2bed/2bath

Location, Comfort, and Privacy! We have all you look for one night or extended stay. This apartment was newly remodeled and designed for you to feel like home. Private garage, lock code system (key-less). Walking distance from Lake Hollingsworth, Morton, local coffee shops, restaurants, gas stations, etc. Lakeland is also conveniently located between Orlando and Tampa. 40minutes from Disney & Bush Gardens, 30min to Legoland, 1 hour from Orlando/Universal, and the gorgeous beaches on the gulf.

Jun 20 – 27

R2,540 ZAR per night

Guesthouse in Lakeland

4.96 out of 5 average rating, 141 reviews

Cozy Studio + Secluded Courtyard, SEU, FSC, dwntwn

Enjoy your stay in Lakeland in our cozy, newly remodeled studio! It is centrally located in Lakeland and a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) It comes fully equipped with everything you will need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the cozy modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Parking is just a few steps down the pathway through the courtyard from your door!

Aug 5 – 12

R1,940 ZAR per night

Home in Lakeland

4.96 out of 5 average rating, 113 reviews

Cute, Historic District Home - GREAT LOCATION

Enjoy a stylish experience at this centrally-located place 5 mins from downtown Lakeland, 8 mins from I-4, 40 mins from Tampa and Orlando (Disney World/Universal), 1 hour from several beaches including Clearwater. 🐕 Pet friendly but you MUST include your pets in the reservation Nearby places of interest: - Downtown Lakeland - Southeastern University and Florida Southern College - RP Funding Center - Lakeland Linder International Airport - Polk Theatre - Circle B Nature Reserve - and more!

Jul 6 – 13

R2,680 ZAR per night

Home in Lakeland

4.9 out of 5 average rating, 41 reviews

The Woodsy Weekender

Take it easy at this unique and tranquil getaway in the woods. Wake up in one of our cozy queen or full sized beds, and enjoy coffee and hot chocolate on the 2nd story deck. 10 minutes from downtown Lakeland, spend your day walking our beautiful lakes and eating at our foodie hotspots. End your day back the at Woodsy Weekender making dinner in our full kitchen and sipping wine on the screened in back porch swings watching the sunset. The perfect little "Safe Haven" cabin for all occasions.

May 31 – Jun 7

R2,201 ZAR per night

Guesthouse in Lakeland

4.9 out of 5 average rating, 30 reviews

Guest Home, Downtown, Lk Morton, FL Southern

Come visit this peaceful and centrally-located home. Fully remodeled. Queen size bed, twin Trundle, comfortable mattresses. Blinds are all double blinds to allow light in, but still allows privacy. Blackout shades in the bedroom. We have stocked the unit with everything we can think of to make your stay comfortable! Location is excellent! Walking distance to Downtown, library, and Black n Brew Coffee House. Driveway is shared parking with main house, assigned parking spots.

Dec 15 – 22

R1,852 ZAR per night

Guest suite in Lakeland

4.81 out of 5 average rating, 205 reviews

Cozy Suite in the Heart of Lakeland

This amazing, private suite is located on one of the most desired streets in all of Lakeland, and right near the beautiful Lake Hollingsworth. It is less than a block away from both the lake and Commonground Park. It is located along the I-4 between Tampa (40 min drive) and Orlando/Disney and its attractions (1 hr drive). It has close access to route 98 and the 570 Polk Pkwy and many other attractions, shopping, restaurants, and entertainment. You will love this place!

Oct 7 – 14

R1,835 ZAR per night

Bungalow in Lakeland

4.99 out of 5 average rating, 98 reviews

Charming Bungalow with Front Porch

Enjoy peace and serenity at this centrally located, charming, 1920's bungalow in Lakeland. You will find the front porch an inviting spot to relax and unwind on this quiet street in the Lake Morton historical district. Downtown Lakeland, a Publix grocery store, Dixieland shopping, restaurants, bars and a liquor store are less than a five minute drive away. FSC, Lake Morton and Lake Hollingsworth with its 3 mile, paved walking trail are within a few, walkable blocks.

Nov 7 – 14

R1,981 ZAR per night

Condo in Lakeland

4.97 out of 5 average rating, 29 reviews

New! Charming Lakefront Condo

Enjoy an experience at this centrally-located place in the heart of Lakeland with a style all its own! Perfect for a stylish atmosphere for work or pleasure. Enjoy the neighborhood park, the wildlife of Lake Hunter, or take a walk to downtown Lakeland with it's many restaurants, entertainment, and more beautiful lakes. Across the street from Lake Hunter & only a mile from Lake Hollingsworth! Just 36 miles from Disney, 43 miles from Universal, & 17 miles from Legoland!

Aug 29 – Sep 5

R1,920 ZAR per night

Home in Lakeland

5.0 out of 5 average rating, 23 reviews

Charming Historic Area Retreat!

Welcome to our charming one-bedroom short-term rental nestled in the scenic Lake Morton Historic District and conveniently located near the prestigious Florida Southern College. This thoughtfully designed accommodation offers a perfect blend of modern comfort and historic charm. Situated just a stone's throw away from the beautiful Lake Hollingsworth and Lake Morton our property provides an easy access to leisurely strolls around the lake and jogging trails.

Dec 21 – 28

R1,638 ZAR per night

Guesthouse in Lakeland

4.98 out of 5 average rating, 212 reviews

Modern lakeside retreat by SEU and FSC

This 1/1 lakefront historic cottage, built in 1920, is separate from the main house with its own entrance, parking, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks and fishing poles are provided for your enjoyment during your stay. Come unwind and enjoy the lake views from the hammock and private beach!

Jun 14 – 21

R2,122 ZAR per night

Home in Lakeland

4.91 out of 5 average rating, 378 reviews

Charming guest house

PRIVATE 1 bedroom 1 bath guest house! NO SHARED SPACES. Private patio with HOT TUB all to yourself during your stay! We’re centrally located in Lakeland between Tampa and Orlando. We’re on a nice quiet 1 acre property out in the country but still within 10 minutes of the mall, local parks, stores, and all major restaurants.

Jul 3 – 10

R1,980 ZAR per night

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Popular amenities for Lakeland-Winter Haven Metropolitan Area vacation rentals

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Air conditioning

Other great vacation rentals in Lakeland-Winter Haven Metropolitan Area

Apartment in Lakeland

5.0 out of 5 average rating, 59 reviews

Lakefront Property with Swans – Walk to Downtown

Jul 21 – 28

R2,170 ZAR per night

Home in Lakeland

4.88 out of 5 average rating, 60 reviews

Charming and comfy apt near downtown

Jul 8 – 15

R1,874 ZAR per night

Guesthouse in Lakeland

4.94 out of 5 average rating, 81 reviews

Beacon Hill Historic District - Cozy Cottage

May 12 – 19

R2,083 ZAR per night

Guesthouse in Lakeland

4.99 out of 5 average rating, 72 reviews

Serenity at Success

Oct 17 – 24

R2,636 ZAR per night

Guesthouse in Lakeland

4.93 out of 5 average rating, 87 reviews

Modern Retreat w/Privacy-Parking

Sep 17 – 24

R1,925 ZAR per night

Home in Lakeland

4.96 out of 5 average rating, 77 reviews

Cozy Lake House Retreat - Amazing Views !

Nov 26 – Dec 3

R2,845 ZAR per night

Home in Lakeland

4.99 out of 5 average rating, 94 reviews

Swan Studio Lakeland

Oct 21 – 28

R1,870 ZAR per night

Home in Lakeland

4.93 out of 5 average rating, 61 reviews

Queen's Suite with King Bed

May 30 – Jun 6

R1,534 ZAR per night

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